[ { "pathScore": "-1.092", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 7499, "pathwayScore": -1.09 }, "uniqueReaction": 0, "children": [ { "depth": 1, "reaction": { "label": "AT ER UA T5 CF TTL LR>>9", "id": 9 }, "molecules": [{ "commercial": true, "inchi": "JACRWUWPXAESPB", "smiles": "O=C(O)C(CO)C1=CC=CC=C1", "id": 9, "pathId": 7499 }] }, { "depth": 1, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 7499 }] } ], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 7499 }], "RXN": "[CH3:9][N:8]1[C@@H:5]2[CH2:6][CH2:7][C@H:1]1[CH2:2][C@@H:3]([CH2:4]2)[OH:10].[cH:19]1[cH:18][cH:17][c:16]([cH:21][cH:20]1)[CH:11]([CH2:14][OH:15])[C:12](=[O:13])O>>[CH3:9][N:8]1[C@@H:5]2[CH2:6][CH2:7][C@H:1]1[CH2:2][C@H:3]([CH2:4]2)[O:10][C:12](=[O:13])[CH:11]([CH2:14][OH:15])[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3;2.6.2;Esterification" }, { "pathScore": "-1.123", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 26033, "pathwayScore": -1.12 }, "uniqueReaction": 1, "children": [ { "depth": 1, "reaction": { "label": "AT UA TTL CF T5 ER>>8", "id": 8 }, "molecules": [{ "commercial": true, "inchi": "OLEWRQVKIUHEJP", "smiles": "COC(=O)C(CO)C1=CC=CC=C1", "id": 8, "pathId": 26033 }] }, { "depth": 1, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 26033 }] } ], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 26033 }], "RXN": "[CH3:10][N:9]1[C@@H:2]2[CH2:3][CH2:4][C@H:5]1[CH2:6][C@H:7]([CH2:1]2)[OH:8].CO[C:12](=[O:11])[CH:13]([CH2:20][OH:21])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>C1=CC(=CC=C1)C.[Na]>[CH3:10][N:9]1[C@@H:2]2[CH2:3][CH2:4][C@H:5]1[CH2:6][C@H:7]([CH2:1]2)[O:8][C:12](=[O:11])[CH:13]([CH2:20][OH:21])[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3;2.6.14;Transesterification" }, { "pathScore": "-1.222", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 164, "pathwayScore": -1.22 }, "uniqueReaction": 3, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.52426, "label": "T5 ER TTL LR AT>>13", "id": 13 }, "uniqueReaction": 2, "children": [ { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 164 }] }, { "depth": 2, "reaction": { "label": "T5 AT UA TTL ER LR>>146", "id": 146 }, "molecules": [{ "commercial": true, "inchi": "WWYDYZMNFQIYPT", "smiles": "O=C(O)C(C(=O)O)C1=CC=CC=C1", "id": 146, "pathId": 164 }] } ], "molecules": [{ "commercial": false, "inchi": "QDTDAWBMOSCLIB", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)O)C3=CC=CC=C3)C2", "id": 13, "pathId": 164 }], "RXN": "[CH3:10][N:3]1[C@@H:2]2[CH2:9][CH2:8][C@H:4]1[CH2:5][C@H:6]([CH2:1]2)[OH:7].[cH:19]1[cH:18][cH:17][c:16]([cH:21][cH:20]1)[CH:13]([C:12](=[O:11])[OH:22])[C:14](=[O:15])O>C(C)N=C=NCCCN(C)C.C1=CC(=CC=N1)N(C)C.Cl.ClCCl>[CH3:10][N:3]1[C@@H:2]2[CH2:9][CH2:8][C@H:4]1[CH2:5][C@H:6]([CH2:1]2)[O:7][C:14](=[O:15])[CH:13]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:12](=[O:11])[OH:22];2.6.2;Esterification" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 164 }], "RXN": "[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[O:15]C;1.7.6;Methyl" }, { "pathScore": "-1.6", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 21225, "pathwayScore": -1.6 }, "uniqueReaction": 5, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 6, "literatureScore": 0, "intrinsicScore": -1.2967, "label": "ER>>20", "id": 20 }, "uniqueReaction": 4, "children": [ { "depth": 2, "reaction": { "label": "T5 AT CF UA>>147", "id": 147 }, "molecules": [{ "commercial": true, "inchi": "FGYDHYCFHBSNPE", "smiles": "CCOC(=O)C(C(=O)OCC)C1=CC=CC=C1", "id": 147, "pathId": 21225 }] }, { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 21225 }] } ], "molecules": [{ "commercial": false, "inchi": "TVCIYBKIJUANQQ", "smiles": "[C@H]12CC[C@H](C[C@@H](C1)OC(=O)C(C(=O)OCC)C3=CC=CC=C3)N2C", "id": 20, "pathId": 21225 }], "RXN": "CCOC(=O)C(c1ccccc1)C(=O)OCC.CN1C2CCC1CC(C2)O>>CC(C)(C)OC(=O)C(C1=CC=CC=CC1)C(=O)O[C@@H]2C[C@H]3CC[C@@H](C2)N3C;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 21225 }], "RXN": "CCO[C:12](=[O:13])[CH:11]([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[C:9](=[O:10])[O:8][C@H:6]2[CH2:5][C@H:4]3[CH2:3][CH2:2][C@@H:1]([CH2:7]2)[N:20]3[CH3:21]>>[CH3:21][N:20]1[C@@H:4]2[CH2:3][CH2:2][C@H:1]1[CH2:7][C@H:6]([CH2:5]2)[O:8][C:9](=[O:10])[CH:11]([CH2:12][OH:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3;7.4.1;Ester" }, { "pathScore": "-1.62", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 1824, "pathwayScore": -1.62 }, "uniqueReaction": 3, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.52426, "label": "T5 ER TTL LR AT>>13", "id": 13 }, "uniqueReaction": 18, "children": [{ "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.21623, "label": "T5 ER AT UA>>14", "id": 14 }, "uniqueReaction": 17, "children": [ { "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.14293, "label": "T5 ER AT UA TTL CF>>166", "id": 166 }, "uniqueReaction": 16, "children": [ { "depth": 4, "reaction": { "label": "ER TTL CF T5 LR UA ALL>>245", "id": 245 }, "molecules": [{ "commercial": true, "inchi": "WVDDGKGOMKODPV", "smiles": "C1(=CC=CC=C1)CO", "id": 245, "pathId": 1824 }] }, { "depth": 4, "reaction": { "label": "T5 AT UA TTL ER LR>>146", "id": 146 }, "molecules": [{ "commercial": true, "inchi": "WWYDYZMNFQIYPT", "smiles": "O=C(O)C(C(=O)O)C1=CC=CC=C1", "id": 146, "pathId": 1824 }] } ], "molecules": [{ "commercial": false, "inchi": "QSBAHMROFICXDC", "smiles": "O=C(O)C(C(=O)OCC1=CC=CC=C1)C2=CC=CC=C2", "id": 166, "pathId": 1824 }], "RXN": "c1ccc(cc1)CO.c1ccc(cc1)CO.c1ccc(cc1)C(C(=O)O)C(=O)O>>c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)OCc3ccccc3;0.0;Unrecognized" }, { "depth": 3, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 1824 }] } ], "molecules": [{ "commercial": false, "inchi": "JVKNBLWGJDJFIF", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OCC3=CC=CC=C3)C4=CC=CC=C4)C2", "id": 14, "pathId": 1824 }], "RXN": "CN1[C@@H]2CC[C@H]1C[C@H](C2)O.c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)[O-]>>CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(C(c3ccccc3)C(=O)OCc4ccccc4)O;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "QDTDAWBMOSCLIB", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)O)C3=CC=CC=C3)C2", "id": 13, "pathId": 1824 }], "RXN": "[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[O:9]Cc4ccccc4>>[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[OH:9];6.2.4;CO2H-Bn" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 1824 }], "RXN": "[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[O:15]C;1.7.6;Methyl" }, { "pathScore": "-1.701", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 21226, "pathwayScore": -1.7 }, "uniqueReaction": 5, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 6, "literatureScore": 0, "intrinsicScore": -1.2967, "label": "ER>>20", "id": 20 }, "uniqueReaction": 6, "children": [ { "depth": 2, "reaction": { "label": "T5 ER AT CF UA LR TTL>>164", "id": 164 }, "molecules": [{ "commercial": true, "inchi": "INQWZSLKTMTMSK", "smiles": "CCOC(=O)C(C(=O)O)C1=CC=CC=C1", "id": 164, "pathId": 21226 }] }, { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 21226 }] } ], "molecules": [{ "commercial": false, "inchi": "TVCIYBKIJUANQQ", "smiles": "[C@H]12CC[C@H](C[C@@H](C1)OC(=O)C(C(=O)OCC)C3=CC=CC=C3)N2C", "id": 20, "pathId": 21226 }], "RXN": "[CH3:3][CH2:2][O:1][C:4](=[O:5])[CH:6]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:7](=[O:8])O.[CH3:21][N:20]1[C@@H:16]2[CH2:17][CH2:18][C@H:19]1[CH2:22][C@@H:23]([CH2:15]2)[OH:24]>>[CH3:3][CH2:2][O:1][C:4](=[O:5])[CH:6]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:7](=[O:8])[O:24][C@H:23]2[CH2:15][C@H:16]3[CH2:17][CH2:18][C@@H:19]([CH2:22]2)[N:20]3[CH3:21];2.6.2;Esterification" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 21226 }], "RXN": "CCO[C:12](=[O:13])[CH:11]([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[C:9](=[O:10])[O:8][C@H:6]2[CH2:5][C@H:4]3[CH2:3][CH2:2][C@@H:1]([CH2:7]2)[N:20]3[CH3:21]>>[CH3:21][N:20]1[C@@H:4]2[CH2:3][CH2:2][C@H:1]1[CH2:7][C@H:6]([CH2:5]2)[O:8][C:9](=[O:10])[CH:11]([CH2:12][OH:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3;7.4.1;Ester" }, { "pathScore": "-1.9", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 1828, "pathwayScore": -1.9 }, "uniqueReaction": 3, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.52426, "label": "T5 ER TTL LR AT>>13", "id": 13 }, "uniqueReaction": 18, "children": [{ "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.21623, "label": "T5 ER AT UA>>14", "id": 14 }, "uniqueReaction": 17, "children": [ { "depth": 3, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 1828 }] }, { "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.14293, "label": "T5 ER AT UA TTL CF>>166", "id": 166 }, "uniqueReaction": 71, "children": [ { "depth": 4, "reaction": { "label": "T5 AT UA TTL ER LR>>146", "id": 146 }, "molecules": [{ "commercial": true, "inchi": "WWYDYZMNFQIYPT", "smiles": "O=C(O)C(C(=O)O)C1=CC=CC=C1", "id": 146, "pathId": 1828 }] }, { "depth": 4, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.4336, "label": "T5 ER UA TTL CF>>764", "id": 764 }, "uniqueReaction": 70, "children": [ { "depth": 5, "reaction": { "label": "ALL>>1396", "id": 1396 }, "molecules": [{ "commercial": false, "inchi": "NFWSQSCIDYBUOU", "smiles": "C1C=CC=C1C", "id": 1396, "pathId": 1828 }] }, { "depth": 5, "reaction": { "label": "T5 UA ALL ER>>804", "id": 804 }, "molecules": [{ "commercial": true, "inchi": "PCLIMKBDDGJMGD", "smiles": "O=C1CCC(=O)N1Br", "id": 804, "pathId": 1828 }] } ], "molecules": [{ "commercial": false, "inchi": "AGEZXYOZHKGVCM", "smiles": "BrCC1=CC=CC=C1", "id": 764, "pathId": 1828 }], "RXN": "CC1=CC=CC1.C1CC(=O)N(C1=O)Br>>c1ccc(cc1)CBr;0.0;Unrecognized" } ], "molecules": [{ "commercial": false, "inchi": "QSBAHMROFICXDC", "smiles": "O=C(O)C(C(=O)OCC1=CC=CC=C1)C2=CC=CC=C2", "id": 166, "pathId": 1828 }], "RXN": "[cH:16]1[cH:15][cH:14][c:19]([cH:18][cH:17]1)[CH2:20]Br.[cH:7]1[cH:6][cH:5][c:4]([cH:9][cH:8]1)[CH:3]([C:2](=[O:1])[OH:13])[C:10](=[O:12])[OH:11]>>[cH:16]1[cH:15][cH:14][c:19]([cH:18][cH:17]1)[CH2:20][O:11][C:10](=[O:12])[CH:3]([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[C:2](=[O:1])[OH:13];2.6.2;Esterification" } ], "molecules": [{ "commercial": false, "inchi": "JVKNBLWGJDJFIF", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OCC3=CC=CC=C3)C4=CC=CC=C4)C2", "id": 14, "pathId": 1828 }], "RXN": "CN1[C@@H]2CC[C@H]1C[C@H](C2)O.c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)[O-]>>CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(C(c3ccccc3)C(=O)OCc4ccccc4)O;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "QDTDAWBMOSCLIB", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)O)C3=CC=CC=C3)C2", "id": 13, "pathId": 1828 }], "RXN": "[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[O:9]Cc4ccccc4>>[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[OH:9];6.2.4;CO2H-Bn" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 1828 }], "RXN": "[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[O:15]C;1.7.6;Methyl" }, { "pathScore": "-2.026", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 16, "pathwayScore": -2.03 }, "uniqueReaction": 21, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -1.0068, "label": "AT T5 UA>>10", "id": 10 }, "uniqueReaction": 20, "children": [ { "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.53706, "label": "T5 AT UA TTL>>156", "id": 156 }, "uniqueReaction": 19, "children": [ { "depth": 3, "reaction": { "label": "AT UA TTL CF T5 ER>>8", "id": 8 }, "molecules": [{ "commercial": true, "inchi": "OLEWRQVKIUHEJP", "smiles": "COC(=O)C(CO)C1=CC=CC=C1", "id": 8, "pathId": 16 }] }, { "depth": 3, "reaction": { "label": "T5 AT ER UA TTL>>192", "id": 192 }, "molecules": [{ "commercial": true, "inchi": "BCNZYOJHNLTNEZ", "smiles": "CC(C)(C)[Si](C)(C)Cl", "id": 192, "pathId": 16 }] } ], "molecules": [{ "commercial": false, "inchi": "JBESXMGDZODMSC", "smiles": "COC(=O)C(CO[Si](C)(C)C(C)(C)C)C1=CC=CC=C1", "id": 156, "pathId": 16 }], "RXN": "[CH3:14][C:15]([CH3:16])([CH3:17])[Si:18]([CH3:19])([CH3:20])Cl.[CH3:13][O:12][C:10](=[O:11])[CH:3]([CH2:2][OH:1])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[CH3:14][C:15]([CH3:16])([CH3:17])[Si:18]([CH3:19])([CH3:20])[O:1][CH2:2][CH:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[O:12][CH3:13];5.3.2;O-TBS" }, { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 16 }] } ], "molecules": [{ "commercial": false, "inchi": "XVCMSYBIFAADGK", "smiles": "CN1C2CCC1CC(OC(=O)C(CO[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C2", "id": 10, "pathId": 16 }], "RXN": "[CH3:26][C:25]([CH3:27])([CH3:28])[Si:12]([CH3:11])([CH3:13])[O:14][CH2:15][CH:16]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[C:17](=[O:18])OC.[CH3:2][N:1]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:9]2)[OH:10]>>[CH3:26][C:25]([CH3:27])([CH3:28])[Si:12]([CH3:11])([CH3:13])[O:14][CH2:15][CH:16]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[C:17](=[O:18])[O:10][CH:8]2[CH2:9][CH:3]3[CH2:4][CH2:5][CH:6]([CH2:7]2)[N:1]3[CH3:2];2.6.14;Transesterification" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 16 }], "RXN": "CC(C)(C)[Si](C)(C)OCC(c1ccccc1)C(=O)OC2CC3CCC(C2)N3C>>CC(C)(C)[Si](C)(C)OCC(c1ccccc1)C(O)OC2CC3CC(C(C2)N3C)I;0.0;Unrecognized" }, { "pathScore": "-2.109", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 166, "pathwayScore": -2.11 }, "uniqueReaction": 3, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.52426, "label": "T5 ER TTL LR AT>>13", "id": 13 }, "uniqueReaction": 7, "children": [ { "depth": 2, "reaction": { "label": "T5 AT CF UA>>147", "id": 147 }, "molecules": [{ "commercial": true, "inchi": "FGYDHYCFHBSNPE", "smiles": "CCOC(=O)C(C(=O)OCC)C1=CC=CC=C1", "id": 147, "pathId": 166 }] }, { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 166 }] } ], "molecules": [{ "commercial": false, "inchi": "QDTDAWBMOSCLIB", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)O)C3=CC=CC=C3)C2", "id": 13, "pathId": 166 }], "RXN": "CCOC(=O)C(c1ccccc1)C(=O)OCC.CN1C2CCC1CC(C2)O>>CC(C)(C)OC(=O)C(C1=CC=CC=CC1)C(=O)O[C@@H]2C[C@H]3CC[C@@H](C2)N3C;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 166 }], "RXN": "[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[O:15]C;1.7.6;Methyl" }, { "pathScore": "-2.176", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 4770, "pathwayScore": -2.18 }, "uniqueReaction": 22, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 6, "literatureScore": 0, "intrinsicScore": -1.2967, "label": "T5 ER AT UA>>14", "id": 14 }, "uniqueReaction": 17, "children": [ { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 4770 }] }, { "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.14293, "label": "T5 ER AT UA TTL CF>>166", "id": 166 }, "uniqueReaction": 16, "children": [ { "depth": 3, "reaction": { "label": "ER TTL CF T5 LR UA ALL>>245", "id": 245 }, "molecules": [{ "commercial": true, "inchi": "WVDDGKGOMKODPV", "smiles": "C1(=CC=CC=C1)CO", "id": 245, "pathId": 4770 }] }, { "depth": 3, "reaction": { "label": "T5 AT UA TTL ER LR>>146", "id": 146 }, "molecules": [{ "commercial": true, "inchi": "WWYDYZMNFQIYPT", "smiles": "O=C(O)C(C(=O)O)C1=CC=CC=C1", "id": 146, "pathId": 4770 }] } ], "molecules": [{ "commercial": false, "inchi": "QSBAHMROFICXDC", "smiles": "O=C(O)C(C(=O)OCC1=CC=CC=C1)C2=CC=CC=C2", "id": 166, "pathId": 4770 }], "RXN": "c1ccc(cc1)CO.c1ccc(cc1)CO.c1ccc(cc1)C(C(=O)O)C(=O)O>>c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)OCc3ccccc3;0.0;Unrecognized" } ], "molecules": [{ "commercial": false, "inchi": "JVKNBLWGJDJFIF", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OCC3=CC=CC=C3)C4=CC=CC=C4)C2", "id": 14, "pathId": 4770 }], "RXN": "CN1[C@@H]2CC[C@H]1C[C@H](C2)O.c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)[O-]>>CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(C(c3ccccc3)C(=O)OCc4ccccc4)O;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 4770 }], "RXN": "[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[O:9]Cc4ccccc4>>[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[OH:9];6.2.4;CO2H-Bn" }, { "pathScore": "-2.207", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 1759, "pathwayScore": -2.21 }, "uniqueReaction": 3, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.52426, "label": "T5 ER TTL LR AT>>13", "id": 13 }, "uniqueReaction": 18, "children": [{ "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.21623, "label": "T5 ER AT UA>>14", "id": 14 }, "uniqueReaction": 17, "children": [ { "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.14293, "label": "T5 ER AT UA TTL CF>>166", "id": 166 }, "uniqueReaction": 24, "children": [{ "depth": 4, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.53313, "label": "T5 AT TTL>>168", "id": 168 }, "uniqueReaction": 23, "children": [ { "depth": 5, "reaction": { "label": "ER TTL CF T5 LR UA ALL>>245", "id": 245 }, "molecules": [{ "commercial": true, "inchi": "WVDDGKGOMKODPV", "smiles": "C1(=CC=CC=C1)CO", "id": 245, "pathId": 1759 }] }, { "depth": 5, "reaction": { "label": "T5 AT UA TTL ER LR>>146", "id": 146 }, "molecules": [{ "commercial": true, "inchi": "WWYDYZMNFQIYPT", "smiles": "O=C(O)C(C(=O)O)C1=CC=CC=C1", "id": 146, "pathId": 1759 }] } ], "molecules": [{ "commercial": false, "inchi": "BNZNLABYYLOHAG", "smiles": "O=C(OCC1=CC=CC=C1)C(C(=O)OCC2=CC=CC=C2)C3=CC=CC=C3", "id": 168, "pathId": 1759 }], "RXN": "c1ccc(cc1)CO.c1ccc(cc1)CO.c1ccc(cc1)C(C(=O)O)C(=O)O>>c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)OCc3ccccc3;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "QSBAHMROFICXDC", "smiles": "O=C(O)C(C(=O)OCC1=CC=CC=C1)C2=CC=CC=C2", "id": 166, "pathId": 1759 }], "RXN": "c1ccc(cc1)CO[C:2](=[O:1])[CH:3]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[C:4](=[O:5])[O:6][CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3>>[cH:11]1[cH:10][cH:9][c:8]([cH:13][cH:12]1)[CH2:7][O:6][C:4](=[O:5])[C:3](=[C:2]=[O:1])[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2;9.5.6;Carboxy" }, { "depth": 3, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 1759 }] } ], "molecules": [{ "commercial": false, "inchi": "JVKNBLWGJDJFIF", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OCC3=CC=CC=C3)C4=CC=CC=C4)C2", "id": 14, "pathId": 1759 }], "RXN": "CN1[C@@H]2CC[C@H]1C[C@H](C2)O.c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)[O-]>>CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(C(c3ccccc3)C(=O)OCc4ccccc4)O;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "QDTDAWBMOSCLIB", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)O)C3=CC=CC=C3)C2", "id": 13, "pathId": 1759 }], "RXN": "[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[O:9]Cc4ccccc4>>[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[OH:9];6.2.4;CO2H-Bn" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 1759 }], "RXN": "[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[O:15]C;1.7.6;Methyl" }, { "pathScore": "-2.266", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 1, "pathwayScore": -2.27 }, "uniqueReaction": 21, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -1.0068, "label": "AT T5 UA>>10", "id": 10 }, "uniqueReaction": 26, "children": [ { "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.2129, "label": "T5 ER AT CF UA TTL LR>>155", "id": 155 }, "uniqueReaction": 25, "children": [ { "depth": 3, "reaction": { "label": "T5 AT ER UA TTL>>192", "id": 192 }, "molecules": [{ "commercial": true, "inchi": "BCNZYOJHNLTNEZ", "smiles": "CC(C)(C)[Si](C)(C)Cl", "id": 192, "pathId": 1 }] }, { "depth": 3, "reaction": { "label": "AT ER UA T5 CF TTL LR>>9", "id": 9 }, "molecules": [{ "commercial": true, "inchi": "JACRWUWPXAESPB", "smiles": "O=C(O)C(CO)C1=CC=CC=C1", "id": 9, "pathId": 1 }] } ], "molecules": [{ "commercial": false, "inchi": "JRSSZSMOQHFGJT", "smiles": "CC(C)(C)[Si](C)(C)OCC(C(=O)O)C1=CC=CC=C1", "id": 155, "pathId": 1 }], "RXN": "[CH3:4][C:3]([CH3:5])([CH3:6])[Si:2]([CH3:1])([CH3:7])Cl.[cH:17]1[cH:16][cH:15][c:8]([cH:19][cH:18]1)[CH:9]([CH2:13][OH:14])[C:10](=[O:12])[OH:11]>>[CH3:4][C:3]([CH3:5])([CH3:6])[Si:2]([CH3:1])([CH3:7])[O:14][CH2:13][CH:9]([c:8]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[C:10](=[O:12])[OH:11];5.3.2;O-TBS" }, { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 1 }] } ], "molecules": [{ "commercial": false, "inchi": "XVCMSYBIFAADGK", "smiles": "CN1C2CCC1CC(OC(=O)C(CO[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C2", "id": 10, "pathId": 1 }], "RXN": "CC(C)(C)[Si](C)(C)OCC(c1ccccc1)C(=O)O.CN1C2CCC1CC(C2)O>>CC(C)(C)[Si](C)(C)OCC(c1ccccc1)C(O)OC2CC3CCC(C2)N3C;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 1 }], "RXN": "CC(C)(C)[Si](C)(C)OCC(c1ccccc1)C(=O)OC2CC3CCC(C2)N3C>>CC(C)(C)[Si](C)(C)OCC(c1ccccc1)C(O)OC2CC3CC(C(C2)N3C)I;0.0;Unrecognized" }, { "pathScore": "-2.362", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 1762, "pathwayScore": -2.36 }, "uniqueReaction": 3, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.52426, "label": "T5 ER TTL LR AT>>13", "id": 13 }, "uniqueReaction": 18, "children": [{ "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.21623, "label": "T5 ER AT UA>>14", "id": 14 }, "uniqueReaction": 17, "children": [ { "depth": 3, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 1762 }] }, { "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.14293, "label": "T5 ER AT UA TTL CF>>166", "id": 166 }, "uniqueReaction": 24, "children": [{ "depth": 4, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.53313, "label": "T5 AT TTL>>168", "id": 168 }, "uniqueReaction": 27, "children": [ { "depth": 5, "reaction": { "label": "TTL CF T5 UA>>468", "id": 468 }, "molecules": [{ "commercial": true, "inchi": "HXITXNWTGFUOAU", "smiles": "C1(B(O)O)=CC=CC=C1", "id": 468, "pathId": 1762 }] }, { "depth": 5, "reaction": { "label": "AT T5 TTL>>720", "id": 720 }, "molecules": [{ "commercial": true, "inchi": "RYFCSKVXWRJEOB", "smiles": "O=C(CC(=O)OCC1=CC=CC=C1)OCC2=CC=CC=C2", "id": 720, "pathId": 1762 }] } ], "molecules": [{ "commercial": false, "inchi": "BNZNLABYYLOHAG", "smiles": "O=C(OCC1=CC=CC=C1)C(C(=O)OCC2=CC=CC=C2)C3=CC=CC=C3", "id": 168, "pathId": 1762 }], "RXN": "B(c1ccccc1)(O)O.c1ccc(cc1)COC(=O)CC(=O)OCc2ccccc2>[O-]C(=O)C.N(CC)(CC)CC.C(Cl)Cl.[Cu+2]>c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)OCc3ccccc3;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "QSBAHMROFICXDC", "smiles": "O=C(O)C(C(=O)OCC1=CC=CC=C1)C2=CC=CC=C2", "id": 166, "pathId": 1762 }], "RXN": "c1ccc(cc1)CO[C:2](=[O:1])[CH:3]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[C:4](=[O:5])[O:6][CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3>>[cH:11]1[cH:10][cH:9][c:8]([cH:13][cH:12]1)[CH2:7][O:6][C:4](=[O:5])[C:3](=[C:2]=[O:1])[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2;9.5.6;Carboxy" } ], "molecules": [{ "commercial": false, "inchi": "JVKNBLWGJDJFIF", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OCC3=CC=CC=C3)C4=CC=CC=C4)C2", "id": 14, "pathId": 1762 }], "RXN": "CN1[C@@H]2CC[C@H]1C[C@H](C2)O.c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)[O-]>>CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(C(c3ccccc3)C(=O)OCc4ccccc4)O;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "QDTDAWBMOSCLIB", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)O)C3=CC=CC=C3)C2", "id": 13, "pathId": 1762 }], "RXN": "[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[O:9]Cc4ccccc4>>[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[OH:9];6.2.4;CO2H-Bn" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 1762 }], "RXN": "[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[O:15]C;1.7.6;Methyl" }, { "pathScore": "-2.39", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 26073, "pathwayScore": -2.39 }, "uniqueReaction": 39, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -1.6289, "label": "TTL>>27", "id": 27 }, "uniqueReaction": 38, "children": [ { "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.15242, "label": "T5 ER AT UA TTL>>171", "id": 171 }, "uniqueReaction": 73, "children": [ { "depth": 3, "reaction": { "label": "AT ER UA T5 CF TTL LR>>9", "id": 9 }, "molecules": [{ "commercial": true, "inchi": "JACRWUWPXAESPB", "smiles": "O=C(O)C(CO)C1=CC=CC=C1", "id": 9, "pathId": 26073 }] }, { "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.18131, "label": "T5 ER LR UA TTL>>785", "id": 785 }, "uniqueReaction": 72, "children": [ { "depth": 4, "reaction": { "label": "CF T5 ER LR UA TTL ALL>>378", "id": 378 }, "molecules": [{ "commercial": true, "inchi": "WPYMKLBDIGXBTP", "smiles": "C1=CC=C(C(O)=O)C=C1", "id": 378, "pathId": 26073 }] }, { "depth": 4, "reaction": { "label": "CF ER UA ALL>>585", "id": 585 }, "molecules": [{ "commercial": false, "inchi": "YGYAWVDWMABLBF", "smiles": "O=C(Cl)Cl", "id": 585, "pathId": 26073 }] } ], "molecules": [{ "commercial": false, "inchi": "PASDCCFISLVPSO", "smiles": "O=C(Cl)C1=CC=CC=C1", "id": 785, "pathId": 26073 }], "RXN": "[cH:5]1[cH:4][cH:3][c:2]([cH:7][cH:6]1)[C:1](=[O:8])O.C(=O)(Cl)Cl>N(C=O)(C)C.C(Cl)Cl>[cH:5]1[cH:4][cH:3][c:2]([cH:7][cH:6]1)[C:1](=[O:8])Cl;9.3.1;Carboxylic" } ], "molecules": [{ "commercial": false, "inchi": "LPTOLYIRVFJZIA", "smiles": "O=C(OCC(C(=O)O)C1=CC=CC=C1)C2=CC=CC=C2", "id": 171, "pathId": 26073 }], "RXN": "[cH:20]1[cH:9][cH:10][c:11]([cH:18][cH:19]1)[CH:12]([CH2:16][OH:17])[C:13](=[O:14])[OH:15].[cH:6]1[cH:1][cH:2][c:3]([cH:4][cH:5]1)[C:7](=[O:8])Cl>>[cH:20]1[cH:9][cH:10][c:11]([cH:18][cH:19]1)[CH:12]([CH2:16][O:17][C:7](=[O:8])[c:3]2[cH:2][cH:1][cH:6][cH:5][cH:4]2)[C:13](=[O:14])[OH:15];2.6.1;Ester" }, { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 26073 }] } ], "molecules": [{ "commercial": false, "inchi": "WQYBHRSEALVNCA", "smiles": "C1[C@@H]2N(C)[C@@H](C[C@@H](C2)OC(C(C3=CC=CC=C3)COC(=O)C4=CC=CC=C4)=O)C1", "id": 27, "pathId": 26073 }], "RXN": "[CH3:10][N:9]1[C@@H:4]2[CH2:5][CH2:6][C@H:7]1[CH2:8][C@H:1]([CH2:3]2)[OH:2].[cH:11]1[cH:12][cH:13][c:14]([cH:28][cH:29]1)[CH:15]([CH2:18][O:19][C:20](=[O:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[C:16](=[O:17])O>>[CH3:10][N:9]1[C@@H:4]2[CH2:5][CH2:6][C@H:7]1[CH2:8][C@H:1]([CH2:3]2)[O:2][C:16](=[O:17])[CH:15]([CH2:18][O:19][C:20](=[O:21])[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[c:14]4[cH:13][cH:12][cH:11][cH:29][cH:28]4;2.6.2;Esterification" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 26073 }], "RXN": "[CH3:4][N:3]1[C@@H:5]2[CH2:21][CH2:1][C@H:2]1[CH2:8][C@H:7]([CH2:6]2)[O:9][C:10](=[O:20])[CH:11]([CH2:18][O:19]C(=O)c3ccccc3)[c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17]4>CO.O=C([O-])[O-].[K+]>[CH3:4][N:3]1[C@@H:5]2[CH2:21][CH2:1][C@H:2]1[CH2:8][C@H:7]([CH2:6]2)[O:9][C:10](=[O:20])[CH:11]([CH2:18][OH:19])[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3;6.3.17;O-Bz" }, { "pathScore": "-2.396", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 5943, "pathwayScore": -2.4 }, "uniqueReaction": 30, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 6, "literatureScore": 0, "intrinsicScore": -1.6289, "label": "T5 ER>>15", "id": 15 }, "uniqueReaction": 29, "children": [ { "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.15374, "label": "T5 ER AT UA CF TTL>>175", "id": 175 }, "uniqueReaction": 28, "children": [ { "depth": 3, "reaction": { "label": "CF ER UA TTL LR>>630", "id": 630 }, "molecules": [{ "commercial": false, "inchi": "DKGAVHZHDRPRBM", "smiles": "CC(C)(O)C", "id": 630, "pathId": 5943 }] }, { "depth": 3, "reaction": { "label": "T5 AT UA TTL ER LR>>146", "id": 146 }, "molecules": [{ "commercial": true, "inchi": "WWYDYZMNFQIYPT", "smiles": "O=C(O)C(C(=O)O)C1=CC=CC=C1", "id": 146, "pathId": 5943 }] } ], "molecules": [{ "commercial": false, "inchi": "GAYVMJFCQSZDPJ", "smiles": "CC(C)(C)OC(=O)C(C(=O)O)C1=CC=CC=C1", "id": 175, "pathId": 5943 }], "RXN": "[CH3:1][C:2]([CH3:4])([CH3:5])[OH:3].[cH:14]1[cH:13][cH:12][c:11]([cH:16][cH:15]1)[CH:8]([C:6](=[O:7])[OH:17])[C:9](=[O:10])O>C1CCOC1.CC(C)N=C=NC(C)C.C1=CC(=CC=N1)N(C)C>[CH3:1][C:2]([CH3:4])([CH3:5])[O:3][C:9](=[O:10])[CH:8]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:6](=[O:7])[OH:17];5.2.1;CO2H-tBu" }, { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 5943 }] } ], "molecules": [{ "commercial": false, "inchi": "JRHPYIIKFHSTSV", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OC(C)(C)C)C3=CC=CC=C3)C2", "id": 15, "pathId": 5943 }], "RXN": "CC(C)(C)OC(=O)C(c1ccccc1)C(=O)O.CN1[C@@H]2CC[C@H]1C[C@@H](C2)O>>CC(C)(C)OC(=O)C(C1=CC=CC=CC1)C(=O)O[C@@H]2C[C@H]3CC[C@@H](C2)N3C;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 5943 }], "RXN": "CC(C)(C)O[C:13](=[O:14])[CH:12]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[C:10](=[O:11])[O:9][C@H:8]2[CH2:21][C@H:3]3[CH2:4][CH2:5][C@@H:6]([CH2:7]2)[N:2]3[CH3:1]>>[CH3:1][N:2]1[C@@H:3]2[CH2:4][CH2:5][C@H:6]1[CH2:7][C@H:8]([CH2:21]2)[O:9][C:10](=[O:11])[CH:12]([CH:13]=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3;7.9.28;Ester" }, { "pathScore": "-2.416", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 2993, "pathwayScore": -2.42 }, "uniqueReaction": 3, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.52426, "label": "T5 ER TTL LR AT>>13", "id": 13 }, "uniqueReaction": 76, "children": [ { "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.57268, "label": "TTL>>458", "id": 458 }, "uniqueReaction": 75, "children": [ { "depth": 3, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 2993 }] }, { "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.25551, "label": "CF T5 ER UA TTL>>522", "id": 522 }, "uniqueReaction": 74, "children": [{ "depth": 4, "reaction": { "label": "AT ER UA T5 CF TTL LR>>9", "id": 9 }, "molecules": [{ "commercial": true, "inchi": "JACRWUWPXAESPB", "smiles": "O=C(O)C(CO)C1=CC=CC=C1", "id": 9, "pathId": 2993 }] }], "molecules": [{ "commercial": false, "inchi": "DDTOOANXAAWWQJ", "smiles": "C1=CC=CC=C1C(C(=O)O)C=O", "id": 522, "pathId": 2993 }], "RXN": "[cH:4]1[cH:3][cH:2][c:1]([cH:6][cH:5]1)[CH:7]([CH2:11][OH:12])[C:8](=[O:10])[OH:9]>O=C(OI1(OC(=O)C)(C2=C(C=CC=C2)C(O1)=O)OC(C)=O)C.ClCCl>[cH:4]1[cH:3][cH:2][c:1]([cH:6][cH:5]1)[CH:7]([CH:11]=[O:12])[C:8](=[O:10])[OH:9];8.1.4;Alcohol" } ], "molecules": [{ "commercial": false, "inchi": "RMBZQGMKGCCRKF", "smiles": "CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(C3=CC=CC=C3)C=O", "id": 458, "pathId": 2993 }], "RXN": "[CH3:10][N:9]1[C@@H:5]2[CH2:4][CH2:3][C@H:2]1[CH2:1][C@@H:7]([CH2:6]2)[OH:8].[cH:19]1[cH:18][cH:17][c:16]([cH:21][cH:20]1)[CH:11]([CH:12]=[O:13])[C:14](=[O:15])O>>[CH3:10][N:9]1[C@@H:5]2[CH2:4][CH2:3][C@H:2]1[CH2:1][C@H:7]([CH2:6]2)[O:8][C:14](=[O:15])[CH:11]([CH:12]=[O:13])[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3;2.6.2;Esterification" }, { "depth": 2, "reaction": { "label": "LR T5 UA TTL ALL>>7", "id": 7 }, "molecules": [{ "commercial": false, "inchi": "XLYOFNOQVPJJNP", "smiles": "O", "id": 7, "pathId": 2993 }] } ], "molecules": [{ "commercial": false, "inchi": "QDTDAWBMOSCLIB", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)O)C3=CC=CC=C3)C2", "id": 13, "pathId": 2993 }], "RXN": "[CH3:1][N:2]1[C@@H:6]2[CH2:5][CH2:4][C@H:3]1[CH2:9][C@H:8]([CH2:7]2)[O:10][C:11](=[O:12])[CH:13]([CH:20]=[O:21])[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3.O>CC(C)(O)C.C(C)(C)=CC.P(=O)(O)(O)[O-].[Na+].[O-][Cl+][O-]>[CH3:1][N:2]1[C@@H:6]2[CH2:5][CH2:4][C@H:3]1[CH2:9][C@H:8]([CH2:7]2)[O:10][C:11](=[O:12])[CH:13]([c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[C:20](=[O:21])O;8.8.3;Aldehyde" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 2993 }], "RXN": "[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[O:15]C;1.7.6;Methyl" }, { "pathScore": "-2.45", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 26070, "pathwayScore": -2.45 }, "uniqueReaction": 39, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -1.6289, "label": "TTL>>27", "id": 27 }, "uniqueReaction": 38, "children": [ { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 26070 }] }, { "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.15242, "label": "T5 ER AT UA TTL>>171", "id": 171 }, "uniqueReaction": 73, "children": [ { "depth": 3, "reaction": { "label": "AT ER UA T5 CF TTL LR>>9", "id": 9 }, "molecules": [{ "commercial": true, "inchi": "JACRWUWPXAESPB", "smiles": "O=C(O)C(CO)C1=CC=CC=C1", "id": 9, "pathId": 26070 }] }, { "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.18131, "label": "T5 ER LR UA TTL>>785", "id": 785 }, "uniqueReaction": 77, "children": [ { "depth": 4, "reaction": { "label": "CF T5 ER LR UA TTL ALL>>378", "id": 378 }, "molecules": [{ "commercial": true, "inchi": "WPYMKLBDIGXBTP", "smiles": "C1=CC=C(C(O)=O)C=C1", "id": 378, "pathId": 26070 }] }, { "depth": 4, "reaction": { "label": "UA T5 ER ALL>>457", "id": 457 }, "molecules": [{ "commercial": false, "inchi": "ZMXDDKWLCZADIW", "smiles": "C(=O)N(C)C", "id": 457, "pathId": 26070 }] }, { "depth": 4, "reaction": { "label": "T5 ER UA TTL ALL>>782", "id": 782 }, "molecules": [{ "commercial": false, "inchi": "CTSLXHKWHWQRSH", "smiles": "O=C(Cl)C(=O)Cl", "id": 782, "pathId": 26070 }] } ], "molecules": [{ "commercial": false, "inchi": "PASDCCFISLVPSO", "smiles": "O=C(Cl)C1=CC=CC=C1", "id": 785, "pathId": 26070 }], "RXN": "CN(C)C=O.[cH:7]1[cH:6][cH:5][c:4]([cH:9][cH:8]1)[C:3](=[O:2])O.C(=O)(C(=O)Cl)[Cl:1]>>[cH:7]1[cH:6][cH:5][c:4]([cH:9][cH:8]1)[C:3](=[O:2])[Cl:1];9.3.1;Carboxylic" } ], "molecules": [{ "commercial": false, "inchi": "LPTOLYIRVFJZIA", "smiles": "O=C(OCC(C(=O)O)C1=CC=CC=C1)C2=CC=CC=C2", "id": 171, "pathId": 26070 }], "RXN": "[cH:20]1[cH:9][cH:10][c:11]([cH:18][cH:19]1)[CH:12]([CH2:16][OH:17])[C:13](=[O:14])[OH:15].[cH:6]1[cH:1][cH:2][c:3]([cH:4][cH:5]1)[C:7](=[O:8])Cl>>[cH:20]1[cH:9][cH:10][c:11]([cH:18][cH:19]1)[CH:12]([CH2:16][O:17][C:7](=[O:8])[c:3]2[cH:2][cH:1][cH:6][cH:5][cH:4]2)[C:13](=[O:14])[OH:15];2.6.1;Ester" } ], "molecules": [{ "commercial": false, "inchi": "WQYBHRSEALVNCA", "smiles": "C1[C@@H]2N(C)[C@@H](C[C@@H](C2)OC(C(C3=CC=CC=C3)COC(=O)C4=CC=CC=C4)=O)C1", "id": 27, "pathId": 26070 }], "RXN": "[CH3:10][N:9]1[C@@H:4]2[CH2:5][CH2:6][C@H:7]1[CH2:8][C@H:1]([CH2:3]2)[OH:2].[cH:11]1[cH:12][cH:13][c:14]([cH:28][cH:29]1)[CH:15]([CH2:18][O:19][C:20](=[O:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[C:16](=[O:17])O>>[CH3:10][N:9]1[C@@H:4]2[CH2:5][CH2:6][C@H:7]1[CH2:8][C@H:1]([CH2:3]2)[O:2][C:16](=[O:17])[CH:15]([CH2:18][O:19][C:20](=[O:21])[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[c:14]4[cH:13][cH:12][cH:11][cH:29][cH:28]4;2.6.2;Esterification" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 26070 }], "RXN": "[CH3:4][N:3]1[C@@H:5]2[CH2:21][CH2:1][C@H:2]1[CH2:8][C@H:7]([CH2:6]2)[O:9][C:10](=[O:20])[CH:11]([CH2:18][O:19]C(=O)c3ccccc3)[c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17]4>CO.O=C([O-])[O-].[K+]>[CH3:4][N:3]1[C@@H:5]2[CH2:21][CH2:1][C@H:2]1[CH2:8][C@H:7]([CH2:6]2)[O:9][C:10](=[O:20])[CH:11]([CH2:18][OH:19])[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3;6.3.17;O-Bz" }, { "pathScore": "-2.456", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 4774, "pathwayScore": -2.46 }, "uniqueReaction": 22, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 6, "literatureScore": 0, "intrinsicScore": -1.2967, "label": "T5 ER AT UA>>14", "id": 14 }, "uniqueReaction": 17, "children": [ { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 4774 }] }, { "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.14293, "label": "T5 ER AT UA TTL CF>>166", "id": 166 }, "uniqueReaction": 71, "children": [ { "depth": 3, "reaction": { "label": "T5 AT UA TTL ER LR>>146", "id": 146 }, "molecules": [{ "commercial": true, "inchi": "WWYDYZMNFQIYPT", "smiles": "O=C(O)C(C(=O)O)C1=CC=CC=C1", "id": 146, "pathId": 4774 }] }, { "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.4336, "label": "T5 ER UA TTL CF>>764", "id": 764 }, "uniqueReaction": 70, "children": [ { "depth": 4, "reaction": { "label": "T5 UA ALL ER>>804", "id": 804 }, "molecules": [{ "commercial": true, "inchi": "PCLIMKBDDGJMGD", "smiles": "O=C1CCC(=O)N1Br", "id": 804, "pathId": 4774 }] }, { "depth": 4, "reaction": { "label": "ALL>>1396", "id": 1396 }, "molecules": [{ "commercial": false, "inchi": "NFWSQSCIDYBUOU", "smiles": "C1C=CC=C1C", "id": 1396, "pathId": 4774 }] } ], "molecules": [{ "commercial": false, "inchi": "AGEZXYOZHKGVCM", "smiles": "BrCC1=CC=CC=C1", "id": 764, "pathId": 4774 }], "RXN": "CC1=CC=CC1.C1CC(=O)N(C1=O)Br>>c1ccc(cc1)CBr;0.0;Unrecognized" } ], "molecules": [{ "commercial": false, "inchi": "QSBAHMROFICXDC", "smiles": "O=C(O)C(C(=O)OCC1=CC=CC=C1)C2=CC=CC=C2", "id": 166, "pathId": 4774 }], "RXN": "[cH:16]1[cH:15][cH:14][c:19]([cH:18][cH:17]1)[CH2:20]Br.[cH:7]1[cH:6][cH:5][c:4]([cH:9][cH:8]1)[CH:3]([C:2](=[O:1])[OH:13])[C:10](=[O:12])[OH:11]>>[cH:16]1[cH:15][cH:14][c:19]([cH:18][cH:17]1)[CH2:20][O:11][C:10](=[O:12])[CH:3]([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[C:2](=[O:1])[OH:13];2.6.2;Esterification" } ], "molecules": [{ "commercial": false, "inchi": "JVKNBLWGJDJFIF", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OCC3=CC=CC=C3)C4=CC=CC=C4)C2", "id": 14, "pathId": 4774 }], "RXN": "CN1[C@@H]2CC[C@H]1C[C@H](C2)O.c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)[O-]>>CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(C(c3ccccc3)C(=O)OCc4ccccc4)O;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 4774 }], "RXN": "[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[O:9]Cc4ccccc4>>[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[OH:9];6.2.4;CO2H-Bn" }, { "pathScore": "-2.465", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 5918, "pathwayScore": -2.47 }, "uniqueReaction": 30, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 6, "literatureScore": 0, "intrinsicScore": -1.6289, "label": "T5 ER>>15", "id": 15 }, "uniqueReaction": 29, "children": [ { "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.15374, "label": "T5 ER AT UA CF TTL>>175", "id": 175 }, "uniqueReaction": 79, "children": [{ "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.31823, "label": "UA CF AT ER T5>>429", "id": 429 }, "uniqueReaction": 78, "children": [{ "depth": 4, "reaction": { "label": "T5 ER AT CF UA LR TTL>>164", "id": 164 }, "molecules": [{ "commercial": true, "inchi": "INQWZSLKTMTMSK", "smiles": "CCOC(=O)C(C(=O)O)C1=CC=CC=C1", "id": 164, "pathId": 5918 }] }], "molecules": [{ "commercial": false, "inchi": "NRCWARMKAGJPHW", "smiles": "CC(C)(OC(C(C(=O)OCC)C1=CC=CC=C1)=O)C", "id": 429, "pathId": 5918 }], "RXN": "[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:7](=[O:8])[OH:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:7](=[O:8])[O:9]Cc2ccccc2;5.3.1;O-Bn" }], "molecules": [{ "commercial": false, "inchi": "GAYVMJFCQSZDPJ", "smiles": "CC(C)(C)OC(=O)C(C(=O)O)C1=CC=CC=C1", "id": 175, "pathId": 5918 }], "RXN": "CCOC(=O)C(c1ccccc1)C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)C(C1=CC=CC=CC1)C(=O)O;0.0;Unrecognized" }, { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 5918 }] } ], "molecules": [{ "commercial": false, "inchi": "JRHPYIIKFHSTSV", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OC(C)(C)C)C3=CC=CC=C3)C2", "id": 15, "pathId": 5918 }], "RXN": "CC(C)(C)OC(=O)C(c1ccccc1)C(=O)O.CN1[C@@H]2CC[C@H]1C[C@@H](C2)O>>CC(C)(C)OC(=O)C(C1=CC=CC=CC1)C(=O)O[C@@H]2C[C@H]3CC[C@@H](C2)N3C;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 5918 }], "RXN": "CC(C)(C)O[C:13](=[O:14])[CH:12]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[C:10](=[O:11])[O:9][C@H:8]2[CH2:21][C@H:3]3[CH2:4][CH2:5][C@@H:6]([CH2:7]2)[N:2]3[CH3:1]>>[CH3:1][N:2]1[C@@H:3]2[CH2:4][CH2:5][C@H:6]1[CH2:7][C@H:8]([CH2:21]2)[O:9][C:10](=[O:11])[CH:12]([CH:13]=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3;7.9.28;Ester" }, { "pathScore": "-2.52", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 21283, "pathwayScore": -2.52 }, "uniqueReaction": 12, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -1.2083, "label": "UA>>24", "id": 24 }, "uniqueReaction": 80, "children": [ { "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.087683, "label": "T5 ER AT CF UA TTL>>159", "id": 159 }, "uniqueReaction": 49, "children": [{ "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.30759, "label": "T5 AT TTL ER UA>>162", "id": 162 }, "uniqueReaction": 48, "children": [ { "depth": 4, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.3272, "label": "T5 ER UA TTL CF>>764", "id": 764 }, "uniqueReaction": 70, "children": [ { "depth": 5, "reaction": { "label": "T5 UA ALL ER>>804", "id": 804 }, "molecules": [{ "commercial": true, "inchi": "PCLIMKBDDGJMGD", "smiles": "O=C1CCC(=O)N1Br", "id": 804, "pathId": 21283 }] }, { "depth": 5, "reaction": { "label": "ALL>>1396", "id": 1396 }, "molecules": [{ "commercial": false, "inchi": "NFWSQSCIDYBUOU", "smiles": "C1C=CC=C1C", "id": 1396, "pathId": 21283 }] } ], "molecules": [{ "commercial": false, "inchi": "AGEZXYOZHKGVCM", "smiles": "BrCC1=CC=CC=C1", "id": 764, "pathId": 21283 }], "RXN": "CC1=CC=CC1.C1CC(=O)N(C1=O)Br>>c1ccc(cc1)CBr;0.0;Unrecognized" }, { "depth": 4, "reaction": { "label": "AT UA TTL CF T5 ER>>8", "id": 8 }, "molecules": [{ "commercial": true, "inchi": "OLEWRQVKIUHEJP", "smiles": "COC(=O)C(CO)C1=CC=CC=C1", "id": 8, "pathId": 21283 }] } ], "molecules": [{ "commercial": false, "inchi": "HZKFLPZHYAMOLW", "smiles": "COC(=O)C(COCC1=CC=CC=C1)C2=CC=CC=C2", "id": 162, "pathId": 21283 }], "RXN": "[CH3:13][O:12][C:10](=[O:11])[CH:3]([CH2:2][OH:1])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.[cH:14]1[cH:15][cH:16][c:17]([cH:18][cH:19]1)[CH2:20]Br>>[CH3:13][O:12][C:10](=[O:11])[CH:3]([CH2:2][O:1][CH2:20][c:17]1[cH:16][cH:15][cH:14][cH:19][cH:18]1)[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2;1.7.9;Williamson" }], "molecules": [{ "commercial": false, "inchi": "UBAAZUSNCMSIKJ", "smiles": "O=C(O)C(COCC1=CC=CC=C1)C2=CC=CC=C2", "id": 159, "pathId": 21283 }], "RXN": "COC(=O)C(COCc1ccccc1)c2ccccc2>>COC(=O)C(COCC1=CC=CC=CC1)c2ccccc2;0.0;Unrecognized" }, { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 21283 }] } ], "molecules": [{ "commercial": false, "inchi": "VJSDMEDOXPYHTG", "smiles": "C1=CC=CC(=C1)C(COCC2=CC=CC=C2)C(=O)O[C@@H]3C[C@H]4CC[C@@H](C3)N4C", "id": 24, "pathId": 21283 }], "RXN": "[CH3:6][N:5]1[C@@H:1]2[CH2:2][CH2:3][C@H:4]1[CH2:7][C@H:8]([CH2:9]2)[OH:10].[cH:27]1[cH:26][cH:25][c:12]([cH:11][cH:28]1)[CH2:13][O:14][CH2:15][CH:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[C:23](=[O:24])O>>[CH3:6][N:5]1[C@@H:1]2[CH2:2][CH2:3][C@H:4]1[CH2:7][C@@H:8]([CH2:9]2)[O:10][C:23](=[O:24])[CH:16]([CH2:15][O:14][CH2:13][c:12]3[cH:25][cH:26][cH:27][cH:28][cH:11]3)[c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4;2.6.2;Esterification" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 21283 }], "RXN": "[CH3:21][N:20]1[C@@H:15]2[CH2:16][CH2:17][C@H:18]1[CH2:19][C@@H:13]([CH2:14]2)[O:12][C:10](=[O:11])[CH:7]([CH2:8][O:9]Cc3ccccc3)[c:5]4[cH:6][cH:1][cH:2][cH:3][cH:4]4>>[CH3:21][N:20]1[C@@H:15]2[CH2:16][CH2:17][C@H:18]1[CH2:19][C@H:13]([CH2:14]2)[O:12][C:10](=[O:11])[CH:7]([CH2:8][OH:9])[c:5]3[cH:6][cH:1][cH:2][cH:3][cH:4]3;6.3.1;O-Bn" }, { "pathScore": "-2.593", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 1836, "pathwayScore": -2.59 }, "uniqueReaction": 3, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.52426, "label": "T5 ER TTL LR AT>>13", "id": 13 }, "uniqueReaction": 18, "children": [{ "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.21623, "label": "T5 ER AT UA>>14", "id": 14 }, "uniqueReaction": 17, "children": [ { "depth": 3, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 1836 }] }, { "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.14293, "label": "T5 ER AT UA TTL CF>>166", "id": 166 }, "uniqueReaction": 82, "children": [ { "depth": 4, "reaction": { "label": "T5 AT UA TTL ER LR>>146", "id": 146 }, "molecules": [{ "commercial": true, "inchi": "WWYDYZMNFQIYPT", "smiles": "O=C(O)C(C(=O)O)C1=CC=CC=C1", "id": 146, "pathId": 1836 }] }, { "depth": 4, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -1.0247, "label": "ER UA TTL T5>>834", "id": 834 }, "uniqueReaction": 81, "children": [ { "depth": 5, "reaction": { "label": "ER TTL ALL T5>>875", "id": 875 }, "molecules": [{ "commercial": false, "inchi": "VZGDMQKNWNREIO", "smiles": "ClC(Cl)(Cl)Cl", "id": 875, "pathId": 1836 }] }, { "depth": 5, "reaction": { "label": "ER TTL CF T5 LR UA ALL>>245", "id": 245 }, "molecules": [{ "commercial": true, "inchi": "WVDDGKGOMKODPV", "smiles": "C1(=CC=CC=C1)CO", "id": 245, "pathId": 1836 }] } ], "molecules": [{ "commercial": false, "inchi": "KCXMKQUNVWSEMD", "smiles": "C1=CC=CC(CCl)=C1", "id": 834, "pathId": 1836 }], "RXN": "[cH:7]1[cH:1][cH:2][c:3]([cH:5][cH:6]1)[CH2:4]O.C(Cl)(Cl)(Cl)Cl>>[cH:7]1[cH:1][cH:2][c:3]([cH:5][cH:6]1)[CH2:4]Cl;9.1.6;Hydroxy" } ], "molecules": [{ "commercial": false, "inchi": "QSBAHMROFICXDC", "smiles": "O=C(O)C(C(=O)OCC1=CC=CC=C1)C2=CC=CC=C2", "id": 166, "pathId": 1836 }], "RXN": "c1ccc(cc1)CCl.c1ccc(cc1)C(C(=O)[O-])C(=O)[O-]>>c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)O;0.0;Unrecognized" } ], "molecules": [{ "commercial": false, "inchi": "JVKNBLWGJDJFIF", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OCC3=CC=CC=C3)C4=CC=CC=C4)C2", "id": 14, "pathId": 1836 }], "RXN": "CN1[C@@H]2CC[C@H]1C[C@H](C2)O.c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)[O-]>>CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(C(c3ccccc3)C(=O)OCc4ccccc4)O;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "QDTDAWBMOSCLIB", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)O)C3=CC=CC=C3)C2", "id": 13, "pathId": 1836 }], "RXN": "[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[O:9]Cc4ccccc4>>[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[OH:9];6.2.4;CO2H-Bn" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 1836 }], "RXN": "[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[O:15]C;1.7.6;Methyl" }, { "pathScore": "-2.593", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 1837, "pathwayScore": -2.59 }, "uniqueReaction": 3, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.52426, "label": "T5 ER TTL LR AT>>13", "id": 13 }, "uniqueReaction": 18, "children": [{ "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.21623, "label": "T5 ER AT UA>>14", "id": 14 }, "uniqueReaction": 17, "children": [ { "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.14293, "label": "T5 ER AT UA TTL CF>>166", "id": 166 }, "uniqueReaction": 82, "children": [ { "depth": 4, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -1.0247, "label": "ER UA TTL T5>>834", "id": 834 }, "uniqueReaction": 83, "children": [ { "depth": 5, "reaction": { "label": "ER TTL CF T5 LR UA ALL>>245", "id": 245 }, "molecules": [{ "commercial": true, "inchi": "WVDDGKGOMKODPV", "smiles": "C1(=CC=CC=C1)CO", "id": 245, "pathId": 1837 }] }, { "depth": 5, "reaction": { "label": "T5 UA TTL ALL>>781", "id": 781 }, "molecules": [{ "commercial": false, "inchi": "FYSNRJHAOHDILO", "smiles": "O=S(Cl)Cl", "id": 781, "pathId": 1837 }] } ], "molecules": [{ "commercial": false, "inchi": "KCXMKQUNVWSEMD", "smiles": "C1=CC=CC(CCl)=C1", "id": 834, "pathId": 1837 }], "RXN": "[cH:8]1[cH:2][cH:3][c:4]([cH:6][cH:7]1)[CH2:5]O.O=S([Cl:1])Cl>ClC(Cl)Cl>[cH:8]1[cH:2][cH:3][c:4]([cH:6][cH:7]1)[CH2:5][Cl:1];9.1.10;Darzens" }, { "depth": 4, "reaction": { "label": "T5 AT UA TTL ER LR>>146", "id": 146 }, "molecules": [{ "commercial": true, "inchi": "WWYDYZMNFQIYPT", "smiles": "O=C(O)C(C(=O)O)C1=CC=CC=C1", "id": 146, "pathId": 1837 }] } ], "molecules": [{ "commercial": false, "inchi": "QSBAHMROFICXDC", "smiles": "O=C(O)C(C(=O)OCC1=CC=CC=C1)C2=CC=CC=C2", "id": 166, "pathId": 1837 }], "RXN": "c1ccc(cc1)CCl.c1ccc(cc1)C(C(=O)[O-])C(=O)[O-]>>c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)O;0.0;Unrecognized" }, { "depth": 3, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 1837 }] } ], "molecules": [{ "commercial": false, "inchi": "JVKNBLWGJDJFIF", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OCC3=CC=CC=C3)C4=CC=CC=C4)C2", "id": 14, "pathId": 1837 }], "RXN": "CN1[C@@H]2CC[C@H]1C[C@H](C2)O.c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)[O-]>>CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(C(c3ccccc3)C(=O)OCc4ccccc4)O;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "QDTDAWBMOSCLIB", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)O)C3=CC=CC=C3)C2", "id": 13, "pathId": 1837 }], "RXN": "[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[O:9]Cc4ccccc4>>[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[OH:9];6.2.4;CO2H-Bn" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 1837 }], "RXN": "[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[O:15]C;1.7.6;Methyl" }, { "pathScore": "-2.614", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 5942, "pathwayScore": -2.61 }, "uniqueReaction": 30, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 6, "literatureScore": 0, "intrinsicScore": -1.6289, "label": "T5 ER>>15", "id": 15 }, "uniqueReaction": 29, "children": [ { "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.15374, "label": "T5 ER AT UA CF TTL>>175", "id": 175 }, "uniqueReaction": 31, "children": [ { "depth": 3, "reaction": { "label": "T5 AT UA TTL ER LR>>146", "id": 146 }, "molecules": [{ "commercial": true, "inchi": "WWYDYZMNFQIYPT", "smiles": "O=C(O)C(C(=O)O)C1=CC=CC=C1", "id": 146, "pathId": 5942 }] }, { "depth": 3, "reaction": { "label": "AT T5 ER TTL UA>>358", "id": 358 }, "molecules": [{ "commercial": true, "inchi": "DYHSDKLCOJIUFX", "smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C", "id": 358, "pathId": 5942 }] } ], "molecules": [{ "commercial": false, "inchi": "GAYVMJFCQSZDPJ", "smiles": "CC(C)(C)OC(=O)C(C(=O)O)C1=CC=CC=C1", "id": 175, "pathId": 5942 }], "RXN": "CC(C)(C)OC(=O)OC(=O)[O:4][C:1]([CH3:2])([CH3:3])[CH3:5].[cH:12]1[cH:11][cH:10][c:9]([cH:14][cH:13]1)[CH:8]([C:6](=[O:7])[OH:17])[C:15](=[O:16])O>C(C)(C)(O)C.C1=CC(=CC=N1)N(C)C>[CH3:2][C:1]([CH3:3])([CH3:5])[O:4][C:15](=[O:16])[CH:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:6](=[O:7])[OH:17];5.2.1;CO2H-tBu" }, { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 5942 }] } ], "molecules": [{ "commercial": false, "inchi": "JRHPYIIKFHSTSV", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OC(C)(C)C)C3=CC=CC=C3)C2", "id": 15, "pathId": 5942 }], "RXN": "CC(C)(C)OC(=O)C(c1ccccc1)C(=O)O.CN1[C@@H]2CC[C@H]1C[C@@H](C2)O>>CC(C)(C)OC(=O)C(C1=CC=CC=CC1)C(=O)O[C@@H]2C[C@H]3CC[C@@H](C2)N3C;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 5942 }], "RXN": "CC(C)(C)O[C:13](=[O:14])[CH:12]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[C:10](=[O:11])[O:9][C@H:8]2[CH2:21][C@H:3]3[CH2:4][CH2:5][C@@H:6]([CH2:7]2)[N:2]3[CH3:1]>>[CH3:1][N:2]1[C@@H:3]2[CH2:4][CH2:5][C@H:6]1[CH2:7][C@H:8]([CH2:21]2)[O:9][C:10](=[O:11])[CH:12]([CH:13]=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3;7.9.28;Ester" }, { "pathScore": "-2.724", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 17, "pathwayScore": -2.72 }, "uniqueReaction": 21, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -1.0068, "label": "AT T5 UA>>10", "id": 10 }, "uniqueReaction": 20, "children": [ { "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.53706, "label": "T5 AT UA TTL>>156", "id": 156 }, "uniqueReaction": 32, "children": [ { "depth": 3, "reaction": { "label": "AT UA TTL CF T5 ER>>8", "id": 8 }, "molecules": [{ "commercial": true, "inchi": "OLEWRQVKIUHEJP", "smiles": "COC(=O)C(CO)C1=CC=CC=C1", "id": 8, "pathId": 17 }] }, { "depth": 3, "reaction": { "label": "T5 AT UA TTL>>193", "id": 193 }, "molecules": [{ "commercial": true, "inchi": "WLLIXJBWWFGEHT", "smiles": "CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F", "id": 193, "pathId": 17 }] } ], "molecules": [{ "commercial": false, "inchi": "JBESXMGDZODMSC", "smiles": "COC(=O)C(CO[Si](C)(C)C(C)(C)C)C1=CC=CC=C1", "id": 156, "pathId": 17 }], "RXN": "[CH3:17][C:16]([CH3:18])([CH3:19])[Si:14]([CH3:15])([CH3:20])OS(=O)(=O)C(F)(F)F.[CH3:11][O:10][C:8](=[O:9])[CH:7]([CH2:12][OH:13])[c:1]1[cH:2][cH:3][cH:4][cH:5][cH:6]1>>[CH3:17][C:16]([CH3:18])([CH3:19])[Si:14]([CH3:15])([CH3:20])[O:13][CH2:12][CH:7]([c:1]1[cH:2][cH:3][cH:4][cH:5][cH:6]1)[C:8](=[O:9])[O:10][CH3:11];5.3.2;O-TBS" }, { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 17 }] } ], "molecules": [{ "commercial": false, "inchi": "XVCMSYBIFAADGK", "smiles": "CN1C2CCC1CC(OC(=O)C(CO[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C2", "id": 10, "pathId": 17 }], "RXN": "[CH3:26][C:25]([CH3:27])([CH3:28])[Si:12]([CH3:11])([CH3:13])[O:14][CH2:15][CH:16]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[C:17](=[O:18])OC.[CH3:2][N:1]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:9]2)[OH:10]>>[CH3:26][C:25]([CH3:27])([CH3:28])[Si:12]([CH3:11])([CH3:13])[O:14][CH2:15][CH:16]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[C:17](=[O:18])[O:10][CH:8]2[CH2:9][CH:3]3[CH2:4][CH2:5][CH:6]([CH2:7]2)[N:1]3[CH3:2];2.6.14;Transesterification" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 17 }], "RXN": "CC(C)(C)[Si](C)(C)OCC(c1ccccc1)C(=O)OC2CC3CCC(C2)N3C>>CC(C)(C)[Si](C)(C)OCC(c1ccccc1)C(O)OC2CC3CC(C(C2)N3C)I;0.0;Unrecognized" }, { "pathScore": "-2.739", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 1922, "pathwayScore": -2.74 }, "uniqueReaction": 3, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.52426, "label": "T5 ER TTL LR AT>>13", "id": 13 }, "uniqueReaction": 18, "children": [{ "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.21623, "label": "T5 ER AT UA>>14", "id": 14 }, "uniqueReaction": 34, "children": [ { "depth": 3, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 1922 }] }, { "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -1.0068, "label": "T5 AT UA TTL>>167", "id": 167 }, "uniqueReaction": 33, "children": [ { "depth": 4, "reaction": { "label": "T5 UA TTL ALL>>781", "id": 781 }, "molecules": [{ "commercial": false, "inchi": "FYSNRJHAOHDILO", "smiles": "O=S(Cl)Cl", "id": 781, "pathId": 1922 }] }, { "depth": 4, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.069888, "label": "T5 ER AT UA TTL CF>>166", "id": 166 }, "uniqueReaction": 16, "children": [ { "depth": 5, "reaction": { "label": "ER TTL CF T5 LR UA ALL>>245", "id": 245 }, "molecules": [{ "commercial": true, "inchi": "WVDDGKGOMKODPV", "smiles": "C1(=CC=CC=C1)CO", "id": 245, "pathId": 1922 }] }, { "depth": 5, "reaction": { "label": "T5 AT UA TTL ER LR>>146", "id": 146 }, "molecules": [{ "commercial": true, "inchi": "WWYDYZMNFQIYPT", "smiles": "O=C(O)C(C(=O)O)C1=CC=CC=C1", "id": 146, "pathId": 1922 }] } ], "molecules": [{ "commercial": false, "inchi": "QSBAHMROFICXDC", "smiles": "O=C(O)C(C(=O)OCC1=CC=CC=C1)C2=CC=CC=C2", "id": 166, "pathId": 1922 }], "RXN": "c1ccc(cc1)CO.c1ccc(cc1)CO.c1ccc(cc1)C(C(=O)O)C(=O)O>>c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)OCc3ccccc3;0.0;Unrecognized" } ], "molecules": [{ "commercial": false, "inchi": "VWOHADKFMSXEIE", "smiles": "O=C(Cl)C(C(=O)OCC1=CC=CC=C1)C2=CC=CC=C2", "id": 167, "pathId": 1922 }], "RXN": "[cH:10]1[cH:9][cH:8][c:7]([cH:12][cH:11]1)[CH2:6][O:5][C:4](=[O:13])[CH:3]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[C:1](=[O:2])O.O=S([Cl:20])Cl>ClCCl>[cH:10]1[cH:9][cH:8][c:7]([cH:12][cH:11]1)[CH2:6][O:5][C:4](=[O:13])[CH:3]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[C:1](=[O:2])[Cl:20];9.3.1;Carboxylic" } ], "molecules": [{ "commercial": false, "inchi": "JVKNBLWGJDJFIF", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OCC3=CC=CC=C3)C4=CC=CC=C4)C2", "id": 14, "pathId": 1922 }], "RXN": "[CH3:1][N:2]1[C@@H:3]2[CH2:4][CH2:5][C@H:6]1[CH2:7][C@H:8]([CH2:10]2)[OH:9].[cH:21]1[cH:20][cH:19][c:18]([cH:23][cH:22]1)[CH2:17][O:16][C:14](=[O:15])[CH:13]([c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[C:12](=[O:11])Cl>>[CH3:1][N:2]1[C@@H:3]2[CH2:4][CH2:5][C@H:6]1[CH2:7][C@H:8]([CH2:10]2)[O:9][C:12](=[O:11])[CH:13]([c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[C:14](=[O:15])[O:16][CH2:17][c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4;2.6.1;Ester" }], "molecules": [{ "commercial": false, "inchi": "QDTDAWBMOSCLIB", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)O)C3=CC=CC=C3)C2", "id": 13, "pathId": 1922 }], "RXN": "[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[O:9]Cc4ccccc4>>[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[OH:9];6.2.4;CO2H-Bn" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 1922 }], "RXN": "[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[O:15]C;1.7.6;Methyl" }, { "pathScore": "-2.752", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 192, "pathwayScore": -2.75 }, "uniqueReaction": 3, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.52426, "label": "T5 ER TTL LR AT>>13", "id": 13 }, "uniqueReaction": 35, "children": [{ "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -1.4605, "label": "T5 ER>>15", "id": 15 }, "uniqueReaction": 29, "children": [ { "depth": 3, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 192 }] }, { "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.15374, "label": "T5 ER AT UA CF TTL>>175", "id": 175 }, "uniqueReaction": 28, "children": [ { "depth": 4, "reaction": { "label": "T5 AT UA TTL ER LR>>146", "id": 146 }, "molecules": [{ "commercial": true, "inchi": "WWYDYZMNFQIYPT", "smiles": "O=C(O)C(C(=O)O)C1=CC=CC=C1", "id": 146, "pathId": 192 }] }, { "depth": 4, "reaction": { "label": "CF ER UA TTL LR>>630", "id": 630 }, "molecules": [{ "commercial": false, "inchi": "DKGAVHZHDRPRBM", "smiles": "CC(C)(O)C", "id": 630, "pathId": 192 }] } ], "molecules": [{ "commercial": false, "inchi": "GAYVMJFCQSZDPJ", "smiles": "CC(C)(C)OC(=O)C(C(=O)O)C1=CC=CC=C1", "id": 175, "pathId": 192 }], "RXN": "[CH3:1][C:2]([CH3:4])([CH3:5])[OH:3].[cH:14]1[cH:13][cH:12][c:11]([cH:16][cH:15]1)[CH:8]([C:6](=[O:7])[OH:17])[C:9](=[O:10])O>C1CCOC1.CC(C)N=C=NC(C)C.C1=CC(=CC=N1)N(C)C>[CH3:1][C:2]([CH3:4])([CH3:5])[O:3][C:9](=[O:10])[CH:8]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:6](=[O:7])[OH:17];5.2.1;CO2H-tBu" } ], "molecules": [{ "commercial": false, "inchi": "JRHPYIIKFHSTSV", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OC(C)(C)C)C3=CC=CC=C3)C2", "id": 15, "pathId": 192 }], "RXN": "CC(C)(C)OC(=O)C(c1ccccc1)C(=O)O.CN1[C@@H]2CC[C@H]1C[C@@H](C2)O>>CC(C)(C)OC(=O)C(C1=CC=CC=CC1)C(=O)O[C@@H]2C[C@H]3CC[C@@H](C2)N3C;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "QDTDAWBMOSCLIB", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)O)C3=CC=CC=C3)C2", "id": 13, "pathId": 192 }], "RXN": "CC(C)(C)O[C:13](=[O:14])[CH:12]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[C:10](=[O:11])[O:9][C@H:8]2[CH2:21][C@H:3]3[CH2:4][CH2:5][C@@H:6]([CH2:7]2)[N:2]3[CH3:1]>>[CH3:1][N:2]1[C@@H:3]2[CH2:4][CH2:5][C@H:6]1[CH2:7][C@H:8]([CH2:21]2)[O:9][C:10](=[O:11])[CH:12]([CH:13]=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3;7.9.28;Ester" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 192 }], "RXN": "[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[O:15]C;1.7.6;Methyl" }, { "pathScore": "-2.763", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 4705, "pathwayScore": -2.76 }, "uniqueReaction": 22, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 6, "literatureScore": 0, "intrinsicScore": -1.2967, "label": "T5 ER AT UA>>14", "id": 14 }, "uniqueReaction": 17, "children": [ { "depth": 2, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 4705 }] }, { "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.14293, "label": "T5 ER AT UA TTL CF>>166", "id": 166 }, "uniqueReaction": 24, "children": [{ "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.53313, "label": "T5 AT TTL>>168", "id": 168 }, "uniqueReaction": 23, "children": [ { "depth": 4, "reaction": { "label": "ER TTL CF T5 LR UA ALL>>245", "id": 245 }, "molecules": [{ "commercial": true, "inchi": "WVDDGKGOMKODPV", "smiles": "C1(=CC=CC=C1)CO", "id": 245, "pathId": 4705 }] }, { "depth": 4, "reaction": { "label": "T5 AT UA TTL ER LR>>146", "id": 146 }, "molecules": [{ "commercial": true, "inchi": "WWYDYZMNFQIYPT", "smiles": "O=C(O)C(C(=O)O)C1=CC=CC=C1", "id": 146, "pathId": 4705 }] } ], "molecules": [{ "commercial": false, "inchi": "BNZNLABYYLOHAG", "smiles": "O=C(OCC1=CC=CC=C1)C(C(=O)OCC2=CC=CC=C2)C3=CC=CC=C3", "id": 168, "pathId": 4705 }], "RXN": "c1ccc(cc1)CO.c1ccc(cc1)CO.c1ccc(cc1)C(C(=O)O)C(=O)O>>c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)OCc3ccccc3;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "QSBAHMROFICXDC", "smiles": "O=C(O)C(C(=O)OCC1=CC=CC=C1)C2=CC=CC=C2", "id": 166, "pathId": 4705 }], "RXN": "c1ccc(cc1)CO[C:2](=[O:1])[CH:3]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[C:4](=[O:5])[O:6][CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3>>[cH:11]1[cH:10][cH:9][c:8]([cH:13][cH:12]1)[CH2:7][O:6][C:4](=[O:5])[C:3](=[C:2]=[O:1])[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2;9.5.6;Carboxy" } ], "molecules": [{ "commercial": false, "inchi": "JVKNBLWGJDJFIF", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OCC3=CC=CC=C3)C4=CC=CC=C4)C2", "id": 14, "pathId": 4705 }], "RXN": "CN1[C@@H]2CC[C@H]1C[C@H](C2)O.c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)[O-]>>CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(C(c3ccccc3)C(=O)OCc4ccccc4)O;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 4705 }], "RXN": "[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[O:9]Cc4ccccc4>>[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[OH:9];6.2.4;CO2H-Bn" }, { "pathScore": "-2.806", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 26034, "pathwayScore": -2.81 }, "uniqueReaction": 87, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.61261, "label": "TTL ER>>25", "id": 25 }, "uniqueReaction": 86, "children": [ { "depth": 2, "reaction": { "label": "AT ER UA T5 CF TTL LR>>9", "id": 9 }, "molecules": [{ "commercial": true, "inchi": "JACRWUWPXAESPB", "smiles": "O=C(O)C(CO)C1=CC=CC=C1", "id": 9, "pathId": 26034 }] }, { "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.12409, "label": "ER CF UA TTL T5>>238", "id": 238 }, "uniqueReaction": 85, "children": [{ "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 6, "literatureScore": 0, "intrinsicScore": -0.32051, "label": "AT T5 ER UA>>640", "id": 640 }, "uniqueReaction": 84, "children": [ { "depth": 4, "reaction": { "label": "UA TTL>>2004", "id": 2004 }, "molecules": [{ "commercial": true, "inchi": "UOHSTKWPZWFYTF", "smiles": "OC1C2CC(=O)CC(N2C)C1", "id": 2004, "pathId": 26034 }] }, { "depth": 4, "reaction": { "label": "UA T5 TTL>>445", "id": 445 }, "molecules": [{ "commercial": false, "inchi": "XMBWDFGMSWQBCA", "smiles": "[I-]", "id": 445, "pathId": 26034 }] } ], "molecules": [{ "commercial": false, "inchi": "IDCGRHYWWZWUQS", "smiles": "CN1C2CC(=O)CC1C(I)C2", "id": 640, "pathId": 26034 }], "RXN": "[CH3:9][N:8]1[CH:1]2[CH2:7][CH:6]([CH:5]1[CH2:4][C:3](=[O:10])[CH2:2]2)O.I>ClCCl.C1=CN=CN1.C1=CC=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>[CH3:9][N:8]1[CH:1]2[CH2:7][CH:6]([CH:5]1[CH2:4][C:3](=[O:10])[CH2:2]2)I;9.1.8;Hydroxy" }], "molecules": [{ "commercial": false, "inchi": "FTJQPYVEWWWTRV", "smiles": "C1[C@@H](O)C[C@@H]2N(C)[C@H]1[C@H](I)C2", "id": 238, "pathId": 26034 }], "RXN": "[CH3:5][N:4]1[CH:3]2[CH2:2][CH:1]([CH:6]1[CH2:7][C:8](=[O:10])[CH2:9]2)[I:11]>>[CH3:5][N:4]1[C@H:3]2[CH2:9][C@@H:8]([CH2:7][C@@H:6]1[C@@H:1]([CH2:2]2)[I:11])[OH:10];7.5.1;Ketone" } ], "molecules": [{ "commercial": false, "inchi": "GFESSMZTLBYICD", "smiles": "C1=CC=CC=C1C(CO)C(O[C@H]2C[C@H]3CC([C@@H](C2)N3C)I)=O", "id": 25, "pathId": 26034 }], "RXN": "[CH3:11][N:5]1[C@H:6]2[CH2:7][C@@H:2]([CH2:3][C@@H:4]1[CH:9]([CH2:8]2)[I:10])[OH:1].[cH:12]1[cH:13][cH:14][c:15]([cH:21][cH:22]1)[CH:16]([CH2:17][OH:18])[C:19](=[O:20])O>C1CCCC(N=C=NC2CCCCC2)C1.N1=CC=C(C=C1)N(C)C.ClCCl.O>[CH3:11][N:5]1[C@H:6]2[CH2:7][C@@H:2]([CH2:3][C@@H:4]1[CH:9]([CH2:8]2)[I:10])[O:1][C:19](=[O:20])[CH:16]([CH2:17][OH:18])[c:15]3[cH:14][cH:13][cH:12][cH:22][cH:21]3;2.6.2;Esterification" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 26034 }], "RXN": "[CH3:20][N:19]1[C@H:14]2[CH2:13][C@@H:12]([CH2:18][C@@H:17]1[CH:16]([CH2:15]2)I)[O:11][C:10](=[O:21])[CH:7]([CH2:8][OH:9])[c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3>C(O)C.[Pd]>[CH3:20][N:19]1[C@@H:14]2[CH2:15][CH2:16][C@H:17]1[CH2:18][C@H:12]([CH2:13]2)[O:11][C:10](=[O:21])[CH:7]([CH2:8][OH:9])[c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3;9.7.141;Deiodination" }, { "pathScore": "-2.82", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 1825, "pathwayScore": -2.82 }, "uniqueReaction": 3, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.52426, "label": "T5 ER TTL LR AT>>13", "id": 13 }, "uniqueReaction": 18, "children": [{ "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.21623, "label": "T5 ER AT UA>>14", "id": 14 }, "uniqueReaction": 17, "children": [ { "depth": 3, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 1825 }] }, { "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.14293, "label": "T5 ER AT UA TTL CF>>166", "id": 166 }, "uniqueReaction": 36, "children": [ { "depth": 4, "reaction": { "label": "T5 AT UA TTL ER LR>>146", "id": 146 }, "molecules": [{ "commercial": true, "inchi": "WWYDYZMNFQIYPT", "smiles": "O=C(O)C(C(=O)O)C1=CC=CC=C1", "id": 146, "pathId": 1825 }] }, { "depth": 4, "reaction": { "label": "T5 ER LR TTL ALL UA>>761", "id": 761 }, "molecules": [{ "commercial": true, "inchi": "HSDAJNMJOMSNEV", "smiles": "O=C(Cl)OCC1=CC=CC=C1", "id": 761, "pathId": 1825 }] } ], "molecules": [{ "commercial": false, "inchi": "QSBAHMROFICXDC", "smiles": "O=C(O)C(C(=O)OCC1=CC=CC=C1)C2=CC=CC=C2", "id": 166, "pathId": 1825 }], "RXN": "[cH:8]1[cH:7][cH:6][c:5]([cH:10][cH:9]1)[CH2:4][O:3][C:2](=[O:1])Cl.[cH:18]1[cH:17][cH:16][c:15]([cH:20][cH:19]1)[CH:11](C(=O)O)[C:12](=[O:13])[OH:14]>>[cH:8]1[cH:7][cH:6][c:5]([cH:10][cH:9]1)[CH2:4][O:3][C:2](=[O:1])[CH:11]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[C:12](=[O:13])[OH:14];3.9.41;Decarboxylative" } ], "molecules": [{ "commercial": false, "inchi": "JVKNBLWGJDJFIF", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OCC3=CC=CC=C3)C4=CC=CC=C4)C2", "id": 14, "pathId": 1825 }], "RXN": "CN1[C@@H]2CC[C@H]1C[C@H](C2)O.c1ccc(cc1)COC(=O)C(c2ccccc2)C(=O)[O-]>>CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(C(c3ccccc3)C(=O)OCc4ccccc4)O;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "QDTDAWBMOSCLIB", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)O)C3=CC=CC=C3)C2", "id": 13, "pathId": 1825 }], "RXN": "[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[O:9]Cc4ccccc4>>[CH3:22][N:17]1[C@@H:16]2[CH2:20][CH2:19][C@H:18]1[CH2:21][C@H:14]([CH2:15]2)[O:13][C:11](=[O:12])[CH:7]([c:6]3[cH:1][cH:2][cH:3][cH:4][cH:5]3)[C:8](=[O:10])[OH:9];6.2.4;CO2H-Bn" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 1825 }], "RXN": "[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[O:15]C;1.7.6;Methyl" }, { "pathScore": "-2.821", "depth": 0, "reaction": { "label": ">>0", "id": 0, "pathId": 167, "pathwayScore": -2.82 }, "uniqueReaction": 3, "children": [{ "depth": 1, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.52426, "label": "T5 ER TTL LR AT>>13", "id": 13 }, "uniqueReaction": 35, "children": [{ "depth": 2, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -1.4605, "label": "T5 ER>>15", "id": 15 }, "uniqueReaction": 29, "children": [ { "depth": 3, "reaction": { "label": "ER UA TTL LR T5 AT CF>>17", "id": 17 }, "molecules": [{ "commercial": true, "inchi": "CYHOMWAPJJPNMW", "smiles": "[C@H]12CC[C@H](N1C)C[C@H](C2)O", "id": 17, "pathId": 167 }] }, { "depth": 3, "reaction": { "scalabilityModelScore": 0, "industrialScore": 10, "literatureScore": 0, "intrinsicScore": -0.15374, "label": "T5 ER AT UA CF TTL>>175", "id": 175 }, "uniqueReaction": 79, "children": [{ "depth": 4, "reaction": { "scalabilityModelScore": 0, "industrialScore": 0, "literatureScore": 0, "intrinsicScore": -0.31823, "label": "UA CF AT ER T5>>429", "id": 429 }, "uniqueReaction": 78, "children": [{ "depth": 5, "reaction": { "label": "T5 ER AT CF UA LR TTL>>164", "id": 164 }, "molecules": [{ "commercial": true, "inchi": "INQWZSLKTMTMSK", "smiles": "CCOC(=O)C(C(=O)O)C1=CC=CC=C1", "id": 164, "pathId": 167 }] }], "molecules": [{ "commercial": false, "inchi": "NRCWARMKAGJPHW", "smiles": "CC(C)(OC(C(C(=O)OCC)C1=CC=CC=C1)=O)C", "id": 429, "pathId": 167 }], "RXN": "[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:7](=[O:8])[OH:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:7](=[O:8])[O:9]Cc2ccccc2;5.3.1;O-Bn" }], "molecules": [{ "commercial": false, "inchi": "GAYVMJFCQSZDPJ", "smiles": "CC(C)(C)OC(=O)C(C(=O)O)C1=CC=CC=C1", "id": 175, "pathId": 167 }], "RXN": "CCOC(=O)C(c1ccccc1)C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)C(C1=CC=CC=CC1)C(=O)O;0.0;Unrecognized" } ], "molecules": [{ "commercial": false, "inchi": "JRHPYIIKFHSTSV", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)OC(C)(C)C)C3=CC=CC=C3)C2", "id": 15, "pathId": 167 }], "RXN": "CC(C)(C)OC(=O)C(c1ccccc1)C(=O)O.CN1[C@@H]2CC[C@H]1C[C@@H](C2)O>>CC(C)(C)OC(=O)C(C1=CC=CC=CC1)C(=O)O[C@@H]2C[C@H]3CC[C@@H](C2)N3C;0.0;Unrecognized" }], "molecules": [{ "commercial": false, "inchi": "QDTDAWBMOSCLIB", "smiles": "CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(C(=O)O)C3=CC=CC=C3)C2", "id": 13, "pathId": 167 }], "RXN": "CC(C)(C)O[C:13](=[O:14])[CH:12]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[C:10](=[O:11])[O:9][C@H:8]2[CH2:21][C@H:3]3[CH2:4][CH2:5][C@@H:6]([CH2:7]2)[N:2]3[CH3:1]>>[CH3:1][N:2]1[C@@H:3]2[CH2:4][CH2:5][C@H:6]1[CH2:7][C@H:8]([CH2:21]2)[O:9][C:10](=[O:11])[CH:12]([CH:13]=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3;7.9.28;Ester" }], "molecules": [{ "commercial": false, "inchi": "RKUNBYITZUJHSG", "smiles": "O(C(C(CO)C1=CC=CC=C1)=O)[C@H]2C[C@@]3(N(C)[C@](C2)(CC3)[H])[H]", "id": 0, "pathId": 167 }], "RXN": "[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[OH:15]>>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH:6]1[CH2:7][CH:8]([CH2:22]2)[O:9][C:10](=[O:11])[CH:12]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:13](=[O:14])[O:15]C;1.7.6;Methyl" } ]