Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC1(C)Cc2cc(C(=O)NS(=O)(=O)C3CC3)ccc2NC1c1cccc(-c2ccc(S(C)(=O)=O)cc2)c1
InChiKey
JXWFDAVFIRYQPJ-UHFFFAOYSA-N
Route Signature
5829c5120c2c17dd848cd07f0364d852f05fb7c6b92e692d48890c86e03e7d37
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_d46aeab24a459ad0e17226c6",
"signature": "5829c5120c2c17dd848cd07f0364d852f05fb7c6b92e692d48890c86e03e7d37",
"contentHash": "04b213f11171132a38c3128a673faec2031ded4fcd476771e9f8ad421e2c8e77",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_45ada40c6177e15ea6f94a75",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01805",
"moleculeId": "sa_badbaf61bb4abac400dc2ac8",
"smiles": "CC1(C)Cc2cc(C(=O)NS(=O)(=O)C3CC3)ccc2NC1c1cccc(-c2ccc(S(C)(=O)=O)cc2)c1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_badbaf61bb4abac400dc2ac8",
"inchikey": "JXWFDAVFIRYQPJ-UHFFFAOYSA-N",
"smiles": "CC1(C)Cc2cc(C(=O)NS(=O)(=O)C3CC3)ccc2NC1c1cccc(-c2ccc(S(C)(=O)=O)cc2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "6024",
"routeId": "sa_d46aeab24a459ad0e17226c6",
"moleculeId": "sa_badbaf61bb4abac400dc2ac8",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_badbaf61bb4abac400dc2ac8",
"inchikey": "JXWFDAVFIRYQPJ-UHFFFAOYSA-N",
"smiles": "CC1(C)Cc2cc(C(=O)NS(=O)(=O)C3CC3)ccc2NC1c1cccc(-c2ccc(S(C)(=O)=O)cc2)c1"
},
"smiles": "CC1(C)Cc2cc(C(=O)NS(=O)(=O)C3CC3)ccc2NC1c1cccc(-c2ccc(S(C)(=O)=O)cc2)c1",
"reactionStepId": "sa_bbdfc92039d2a14de787f53c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130023518A1;0971;1326120\",\"rsmi\":\"O[C:8]([c:7]1[cH:6][c:5]2[c:19]([cH:18][cH:17]1)[NH:20][CH:21]([c:22]1[cH:23][cH:24][cH:25][c:26](-[c:27]3[cH:28][cH:29][c:30]([S:31]([CH3:32])(=[O:33])=[O:34])[cH:35][cH:36]3)[cH:37]1)[C:2]([CH3:1])([CH3:3])[CH2:4]2)=[O:9].[NH2:10][S:11](=[O:12])(=[O:13])[CH:14]1[CH2:15][CH2:16]1>CN(C)C=O.O=C(n1ccnc1)n1ccnc1.[HH].[Na+]>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[NH:10][S:11](=[O:12])(=[O:13])[CH:14]3[CH2:15][CH2:16]3)[cH:17][cH:18][c:19]2[NH:20][CH:21]1[c:22]1[cH:23][cH:24][cH:25][c:26](-[c:27]2[cH:28][cH:29][c:30]([S:31]([CH3:32])(=[O:33])=[O:34])[cH:35][cH:36]2)[cH:37]1\"},\"mapped_reaction_smiles\":\"O[C:8]([c:7]1[cH:6][c:5]2[c:19]([cH:18][cH:17]1)[NH:20][CH:21]([c:22]1[cH:23][cH:24][cH:25][c:26](-[c:27]3[cH:28][cH:29][c:30]([S:31]([CH3:32])(=[O:33])=[O:34])[cH:35][cH:36]3)[cH:37]1)[C:2]([CH3:1])([CH3:3])[CH2:4]2)=[O:9].[NH2:10][S:11](=[O:12])(=[O:13])[CH:14]1[CH2:15][CH2:16]1>CN(C)C=O.O=C(n1ccnc1)n1ccnc1.[HH].[Na+]>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[NH:10][S:11](=[O:12])(=[O:13])[CH:14]3[CH2:15][CH2:16]3)[cH:17][cH:18][c:19]2[NH:20][CH:21]1[c:22]1[cH:23][cH:24][cH:25][c:26](-[c:27]2[cH:28][cH:29][c:30]([S:31]([CH3:32])(=[O:33])=[O:34])[cH:35][cH:36]2)[cH:37]1\"}",
"reactionStep": {
"id": "sa_bbdfc92039d2a14de787f53c",
"reactionHash": "1405df6a50e3d3525ef5587eb48b0e7a29545f480a2b2bedaea9cf62982c2fd5"
},
"children": [
{
"id": "6025",
"routeId": "sa_d46aeab24a459ad0e17226c6",
"moleculeId": "sa_5a1e699fe319b6b63517ddb0",
"parentId": "6024",
"isLeaf": false,
"molecule": {
"id": "sa_5a1e699fe319b6b63517ddb0",
"inchikey": "FICZETJSKVYCFR-UHFFFAOYSA-N",
"smiles": "CC1(C)Cc2cc(C(=O)O)ccc2NC1c1cccc(-c2ccc(S(C)(=O)=O)cc2)c1"
},
"smiles": "CC1(C)Cc2cc(C(=O)O)ccc2NC1c1cccc(-c2ccc(S(C)(=O)=O)cc2)c1",
"reactionStepId": "sa_6747a4c114eb9d0e9c8b8a97",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130023518A1;0970;1326119\",\"rsmi\":\"Br[c:20]1[cH:19][cH:18][cH:17][c:16]([CH:15]2[C:2]([CH3:1])([CH3:3])[CH2:4][c:5]3[cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12][c:13]3[NH:14]2)[cH:31]1.OB(O)[c:21]1[cH:22][cH:23][c:24]([S:25]([CH3:26])(=[O:27])=[O:28])[cH:29][cH:30]1>C1COCCO1.CCOC(C)=O.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12][c:13]2[NH:14][CH:15]1[c:16]1[cH:17][cH:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([S:25]([CH3:26])(=[O:27])=[O:28])[cH:29][cH:30]2)[cH:31]1\"},\"mapped_reaction_smiles\":\"Br[c:20]1[cH:19][cH:18][cH:17][c:16]([CH:15]2[C:2]([CH3:1])([CH3:3])[CH2:4][c:5]3[cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12][c:13]3[NH:14]2)[cH:31]1.OB(O)[c:21]1[cH:22][cH:23][c:24]([S:25]([CH3:26])(=[O:27])=[O:28])[cH:29][cH:30]1>C1COCCO1.CCOC(C)=O.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12][c:13]2[NH:14][CH:15]1[c:16]1[cH:17][cH:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([S:25]([CH3:26])(=[O:27])=[O:28])[cH:29][cH:30]2)[cH:31]1\"}",
"reactionStep": {
"id": "sa_6747a4c114eb9d0e9c8b8a97",
"reactionHash": "dfd93eadc06720bfde4902e94714545327b721a6b656754b23ebe5b3f0a28ad2"
},
"children": [
{
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"routeId": "sa_d46aeab24a459ad0e17226c6",
"moleculeId": "sa_1f2848141eb60b21bcb84aff",
"parentId": "6025",
"isLeaf": false,
"molecule": {
"id": "sa_1f2848141eb60b21bcb84aff",
"inchikey": "NVOUSCQUPBGJHD-UHFFFAOYSA-N",
"smiles": "CC1(C)Cc2cc(C(=O)O)ccc2NC1c1cccc(Br)c1"
},
"smiles": "CC1(C)Cc2cc(C(=O)O)ccc2NC1c1cccc(Br)c1",
"reactionStepId": "sa_3f018da130aadc99e378425b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130023518A1;0474;1325779\",\"rsmi\":\"CC[O:10][C:8]([c:7]1[cH:6][c:5]2[c:13]([cH:12][cH:11]1)[NH:14][CH:15]([c:16]1[cH:17][c:18]([Br:19])[cH:20][cH:21][cH:22]1)[C:2]([CH3:1])([CH3:3])[CH2:4]2)=[O:9]>C1CCOC1.CO.Cl.O.[Na+].O>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12][c:13]2[NH:14][CH:15]1[c:16]1[cH:17][c:18]([Br:19])[cH:20][cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"CC[O:10][C:8]([c:7]1[cH:6][c:5]2[c:13]([cH:12][cH:11]1)[NH:14][CH:15]([c:16]1[cH:17][c:18]([Br:19])[cH:20][cH:21][cH:22]1)[C:2]([CH3:1])([CH3:3])[CH2:4]2)=[O:9]>C1CCOC1.CO.Cl.O.[Na+].O>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12][c:13]2[NH:14][CH:15]1[c:16]1[cH:17][c:18]([Br:19])[cH:20][cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_3f018da130aadc99e378425b",
"reactionHash": "47d5ff36c8c78ebdc8f1c667d1fb7eea08f58f03065e2cfe872bfb49bc2b58e3"
},
"children": [
{
"id": "6027",
"routeId": "sa_d46aeab24a459ad0e17226c6",
"moleculeId": "sa_326d8cf2360c814d7125e5c3",
"parentId": "6026",
"isLeaf": false,
"molecule": {
"id": "sa_326d8cf2360c814d7125e5c3",
"inchikey": "GOOPOWIAEGGHBQ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ccc2c(c1)CC(C)(C)C(c1cccc(Br)c1)N2"
},
"smiles": "CCOC(=O)c1ccc2c(c1)CC(C)(C)C(c1cccc(Br)c1)N2",
"reactionStepId": "sa_2b1d79269472397256c29a84",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130023518A1;0448;1325761\",\"rsmi\":\"O[CH:22]1[C:19]([CH3:20])([CH3:21])[CH:11]([c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]2)[NH:10][c:9]2[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:24][c:23]21>CC[SiH](CC)CC.O=C(O)C(F)(F)F>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:23]([cH:24]1)[CH2:22][C:19]([CH3:20])([CH3:21])[CH:11]([c:12]1[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]1)[NH:10]2\"},\"mapped_reaction_smiles\":\"O[CH:22]1[C:19]([CH3:20])([CH3:21])[CH:11]([c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]2)[NH:10][c:9]2[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:24][c:23]21>CC[SiH](CC)CC.O=C(O)C(F)(F)F>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:23]([cH:24]1)[CH2:22][C:19]([CH3:20])([CH3:21])[CH:11]([c:12]1[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]1)[NH:10]2\"}",
"reactionStep": {
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"reactionHash": "757e42720d36f18b88503fcf34881aa19d36c14bcaf528691414c9358a2ee9fb"
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"children": [
{
"id": "6028",
"routeId": "sa_d46aeab24a459ad0e17226c6",
"moleculeId": "sa_037d6290449780d79ca682bf",
"parentId": "6027",
"isLeaf": false,
"molecule": {
"id": "sa_037d6290449780d79ca682bf",
"inchikey": "KPZPNBHFUWNUMS-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ccc2c(c1)C(O)C(C)(C)C(c1cccc(Br)c1)N2"
},
"smiles": "CCOC(=O)c1ccc2c(c1)C(O)C(C)(C)C(c1cccc(Br)c1)N2",
"reactionStepId": "sa_f2857427929ee76199e789db",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130023518A1;0712;1325940\",\"rsmi\":\"[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([N:10]=[CH:11][c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]2)[cH:24][cH:25]1.[CH:19]([CH3:20])([CH3:21])[CH:22]=[O:23]>C1CCOC1.O.O.O=S(=O)(O)C(F)(F)F.O=S(=O)(O)C(F)(F)F.O=S(=O)(O)C(F)(F)F.[Yb+3]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:24]([cH:25]1)[CH:22]([OH:23])[C:19]([CH3:20])([CH3:21])[CH:11]([c:12]1[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]1)[NH:10]2\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([N:10]=[CH:11][c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]2)[cH:24][cH:25]1.[CH:19]([CH3:20])([CH3:21])[CH:22]=[O:23]>C1CCOC1.O.O.O=S(=O)(O)C(F)(F)F.O=S(=O)(O)C(F)(F)F.O=S(=O)(O)C(F)(F)F.[Yb+3]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:24]([cH:25]1)[CH:22]([OH:23])[C:19]([CH3:20])([CH3:21])[CH:11]([c:12]1[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]1)[NH:10]2\"}",
"reactionStep": {
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"children": [
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"moleculeId": "sa_82f3513a4c069ccf25937df3",
"parentId": "6028",
"isLeaf": true,
"molecule": {
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"inchikey": "AMIMRNSIRUDHCM-UHFFFAOYSA-N",
"smiles": "CC(C)C=O"
},
"smiles": "CC(C)C=O",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "6030",
"routeId": "sa_d46aeab24a459ad0e17226c6",
"moleculeId": "sa_0cd15c35add0f46fa5ba821a",
"parentId": "6028",
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"molecule": {
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"inchikey": "LUMLPYZEODWONB-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ccc(N=Cc2cccc(Br)c2)cc1"
},
"smiles": "CCOC(=O)c1ccc(N=Cc2cccc(Br)c2)cc1",
"reactionStepId": "sa_dbee6c691bfa89d0b3133cc9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130023518A1;0711;1325939\",\"rsmi\":\"O=[CH:11][c:12]1[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:19][cH:20]1>CCO>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([N:10]=[CH:11][c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]2)[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"O=[CH:11][c:12]1[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:19][cH:20]1>CCO>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([N:10]=[CH:11][c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]2)[cH:19][cH:20]1\"}",
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"smiles": "CCOC(=O)c1ccc(N)cc1",
"reactionStepId": null,
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},
{
"id": "6032",
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"moleculeId": "sa_e97eecb1d790ff7c7b09842a",
"parentId": "6030",
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"molecule": {
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"inchikey": "SUISZCALMBHJQX-UHFFFAOYSA-N",
"smiles": "O=Cc1cccc(Br)c1"
},
"smiles": "O=Cc1cccc(Br)c1",
"reactionStepId": null,
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}
]
}
]
}
]
}
]
},
{
"id": "6033",
"routeId": "sa_d46aeab24a459ad0e17226c6",
"moleculeId": "sa_f8ea3e5b8d2a13fb7dcec1d6",
"parentId": "6025",
"isLeaf": true,
"molecule": {
"id": "sa_f8ea3e5b8d2a13fb7dcec1d6",
"inchikey": "VDUKDQTYMWUSAC-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)c1ccc(B(O)O)cc1"
},
"smiles": "CS(=O)(=O)c1ccc(B(O)O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "6034",
"routeId": "sa_d46aeab24a459ad0e17226c6",
"moleculeId": "sa_139250787da0cda036eb8caf",
"parentId": "6024",
"isLeaf": true,
"molecule": {
"id": "sa_139250787da0cda036eb8caf",
"inchikey": "WMSPXQIQBQAWLL-UHFFFAOYSA-N",
"smiles": "NS(=O)(=O)C1CC1"
},
"smiles": "NS(=O)(=O)C1CC1",
"reactionStepId": null,
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}
]
}
}