Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4cccc(CNCc5ccsc5)c4)cc23)CC1
InChiKey
SVIZTUNGZYLRLC-UHFFFAOYSA-N
Route Signature
3d766f2bceaef72498bb449d33a0bffbaf0d642c89f77913a229cd1d34d3ead4
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_ea27bdfaa7f2a4a00e4beda6",
"signature": "3d766f2bceaef72498bb449d33a0bffbaf0d642c89f77913a229cd1d34d3ead4",
"contentHash": "6453036f008590d4d5307445d4acb04cdc8a0521c2c7ad48b5bc1766e037d129",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_2ee5eaae488b37f290c747ed",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00457",
"moleculeId": "sa_7047a33aa631dbad8a47ac57",
"smiles": "CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4cccc(CNCc5ccsc5)c4)cc23)CC1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_7047a33aa631dbad8a47ac57",
"inchikey": "SVIZTUNGZYLRLC-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4cccc(CNCc5ccsc5)c4)cc23)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13312",
"routeId": "sa_ea27bdfaa7f2a4a00e4beda6",
"moleculeId": "sa_7047a33aa631dbad8a47ac57",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7047a33aa631dbad8a47ac57",
"inchikey": "SVIZTUNGZYLRLC-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4cccc(CNCc5ccsc5)c4)cc23)CC1"
},
"smiles": "CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4cccc(CNCc5ccsc5)c4)cc23)CC1",
"reactionStepId": "sa_2555ab5042231699e10e99e8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090143372A1;1087;719354\",\"rsmi\":\"O=[CH:23][c:22]1[cH:21][c:20](-[c:19]2[cH:18][c:14]([C:15]([NH2:16])=[O:17])[c:13]3[nH:12][cH:11][c:10]([CH:9]4[CH2:8][CH2:7][N:6]([S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])[CH2:37][CH2:36]4)[c:35]3[cH:34]2)[cH:33][cH:32][cH:31]1.[NH2:24][CH2:25][c:26]1[cH:27][s:28][cH:29][cH:30]1>CC(=O)OB(OC(C)=O)OC(C)=O.[Na+]>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][nH:12][c:13]3[c:14]([C:15]([NH2:16])=[O:17])[cH:18][c:19](-[c:20]4[cH:21][c:22]([CH2:23][NH:24][CH2:25][c:26]5[cH:27][s:28][cH:29][cH:30]5)[cH:31][cH:32][cH:33]4)[cH:34][c:35]23)[CH2:36][CH2:37]1\"},\"mapped_reaction_smiles\":\"O=[CH:23][c:22]1[cH:21][c:20](-[c:19]2[cH:18][c:14]([C:15]([NH2:16])=[O:17])[c:13]3[nH:12][cH:11][c:10]([CH:9]4[CH2:8][CH2:7][N:6]([S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])[CH2:37][CH2:36]4)[c:35]3[cH:34]2)[cH:33][cH:32][cH:31]1.[NH2:24][CH2:25][c:26]1[cH:27][s:28][cH:29][cH:30]1>CC(=O)OB(OC(C)=O)OC(C)=O.[Na+]>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][nH:12][c:13]3[c:14]([C:15]([NH2:16])=[O:17])[cH:18][c:19](-[c:20]4[cH:21][c:22]([CH2:23][NH:24][CH2:25][c:26]5[cH:27][s:28][cH:29][cH:30]5)[cH:31][cH:32][cH:33]4)[cH:34][c:35]23)[CH2:36][CH2:37]1\"}",
"reactionStep": {
"id": "sa_2555ab5042231699e10e99e8",
"reactionHash": "4b8d80270b4dcb93d25b2733f6414f9d6e5a66a553d5993837230a4633a88f22"
},
"children": [
{
"id": "13313",
"routeId": "sa_ea27bdfaa7f2a4a00e4beda6",
"moleculeId": "sa_80aaf0beed92699bfcf63af3",
"parentId": "13312",
"isLeaf": true,
"molecule": {
"id": "sa_80aaf0beed92699bfcf63af3",
"inchikey": "DUDAKCCDHRNMDJ-UHFFFAOYSA-N",
"smiles": "NCc1ccsc1"
},
"smiles": "NCc1ccsc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "13314",
"routeId": "sa_ea27bdfaa7f2a4a00e4beda6",
"moleculeId": "sa_584f38d9add1607b748a9ece",
"parentId": "13312",
"isLeaf": false,
"molecule": {
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"inchikey": "RVTWDQDUGBXRAX-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4cccc(C=O)c4)cc23)CC1"
},
"smiles": "CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4cccc(C=O)c4)cc23)CC1",
"reactionStepId": "sa_ea8dd0fb367c12127222dff5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090143372A1;0997;719321\",\"rsmi\":\"[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][nH:12][c:13]3[c:14]([C:15]([NH2:16])=[O:17])[cH:18][c:19](-[c:20]4[cH:21][c:22]([CH2:23][OH:24])[cH:25][cH:26][cH:27]4)[cH:28][c:29]23)[CH2:30][CH2:31]1>C1CCOC1.O=[Mn]=O>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][nH:12][c:13]3[c:14]([C:15]([NH2:16])=[O:17])[cH:18][c:19](-[c:20]4[cH:21][c:22]([CH:23]=[O:24])[cH:25][cH:26][cH:27]4)[cH:28][c:29]23)[CH2:30][CH2:31]1\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][nH:12][c:13]3[c:14]([C:15]([NH2:16])=[O:17])[cH:18][c:19](-[c:20]4[cH:21][c:22]([CH2:23][OH:24])[cH:25][cH:26][cH:27]4)[cH:28][c:29]23)[CH2:30][CH2:31]1>C1CCOC1.O=[Mn]=O>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][nH:12][c:13]3[c:14]([C:15]([NH2:16])=[O:17])[cH:18][c:19](-[c:20]4[cH:21][c:22]([CH:23]=[O:24])[cH:25][cH:26][cH:27]4)[cH:28][c:29]23)[CH2:30][CH2:31]1\"}",
"reactionStep": {
"id": "sa_ea8dd0fb367c12127222dff5",
"reactionHash": "aec9d7dc8b105bc1306bdb621677dabe03c1855e255d5533c9886c4faf4fb1ad"
},
"children": [
{
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"moleculeId": "sa_d70e1ab20ad9f83938723959",
"parentId": "13314",
"isLeaf": false,
"molecule": {
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"inchikey": "IIOXFJFITRDKDP-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4cccc(CO)c4)cc23)CC1"
},
"smiles": "CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4cccc(CO)c4)cc23)CC1",
"reactionStepId": "sa_9b4f193abee965dade490ddf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090143372A1;0993;719320\",\"rsmi\":\"Br[c:19]1[cH:18][c:14]([C:15]([NH2:16])=[O:17])[c:13]2[nH:12][cH:11][c:10]([CH:9]3[CH2:8][CH2:7][N:6]([S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])[CH2:31][CH2:30]3)[c:29]2[cH:28]1.OB(O)[c:20]1[cH:21][c:22]([CH2:23][OH:24])[cH:25][cH:26][cH:27]1>C1COCCO1.O.O=P(O)(O)O.[K+].[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][nH:12][c:13]3[c:14]([C:15]([NH2:16])=[O:17])[cH:18][c:19](-[c:20]4[cH:21][c:22]([CH2:23][OH:24])[cH:25][cH:26][cH:27]4)[cH:28][c:29]23)[CH2:30][CH2:31]1\"},\"mapped_reaction_smiles\":\"Br[c:19]1[cH:18][c:14]([C:15]([NH2:16])=[O:17])[c:13]2[nH:12][cH:11][c:10]([CH:9]3[CH2:8][CH2:7][N:6]([S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])[CH2:31][CH2:30]3)[c:29]2[cH:28]1.OB(O)[c:20]1[cH:21][c:22]([CH2:23][OH:24])[cH:25][cH:26][cH:27]1>C1COCCO1.O.O=P(O)(O)O.[K+].[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][nH:12][c:13]3[c:14]([C:15]([NH2:16])=[O:17])[cH:18][c:19](-[c:20]4[cH:21][c:22]([CH2:23][OH:24])[cH:25][cH:26][cH:27]4)[cH:28][c:29]23)[CH2:30][CH2:31]1\"}",
"reactionStep": {
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"children": [
{
"id": "13316",
"routeId": "sa_ea27bdfaa7f2a4a00e4beda6",
"moleculeId": "sa_370011e2080c35e36130e003",
"parentId": "13315",
"isLeaf": true,
"molecule": {
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"inchikey": "HGTDLKXUWVKLQX-UHFFFAOYSA-N",
"smiles": "OCc1cccc(B(O)O)c1"
},
"smiles": "OCc1cccc(B(O)O)c1",
"reactionStepId": null,
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},
{
"id": "13317",
"routeId": "sa_ea27bdfaa7f2a4a00e4beda6",
"moleculeId": "sa_22affc3ce098099c872e3723",
"parentId": "13315",
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"molecule": {
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"inchikey": "YSYDQWIOUPGJKJ-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(Br)cc23)CC1"
},
"smiles": "CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(Br)cc23)CC1",
"reactionStepId": "sa_bfccd10e52f4bdc2230ff503",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090143372A1;0988;719318\",\"rsmi\":\"Cl[S:3]([CH2:2][CH3:1])(=[O:4])=[O:5].[NH:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][nH:12][c:13]3[c:14]([C:15]([NH2:16])=[O:17])[cH:18][c:19]([Br:20])[cH:21][c:22]23)[CH2:23][CH2:24]1>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl.O>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][nH:12][c:13]3[c:14]([C:15]([NH2:16])=[O:17])[cH:18][c:19]([Br:20])[cH:21][c:22]23)[CH2:23][CH2:24]1\"},\"mapped_reaction_smiles\":\"Cl[S:3]([CH2:2][CH3:1])(=[O:4])=[O:5].[NH:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][nH:12][c:13]3[c:14]([C:15]([NH2:16])=[O:17])[cH:18][c:19]([Br:20])[cH:21][c:22]23)[CH2:23][CH2:24]1>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl.O>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][nH:12][c:13]3[c:14]([C:15]([NH2:16])=[O:17])[cH:18][c:19]([Br:20])[cH:21][c:22]23)[CH2:23][CH2:24]1\"}",
"reactionStep": {
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"children": [
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"smiles": "NC(=O)c1cc(Br)cc2c(C3CCNCC3)c[nH]c12"
},
"smiles": "NC(=O)c1cc(Br)cc2c(C3CCNCC3)c[nH]c12",
"reactionStepId": "sa_402e7324117cf8330da99aa0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090143372A1;0985;719317\",\"rsmi\":\"CC(C)(C)OC(=O)[N:12]1[CH2:11][CH2:10][CH:9]([c:8]2[cH:7][nH:6][c:5]3[c:4]([C:2]([NH2:1])=[O:3])[cH:19][c:17]([Br:18])[cH:16][c:15]32)[CH2:14][CH2:13]1>C1COCCO1.CO.Cl>[NH2:1][C:2](=[O:3])[c:4]1[c:5]2[nH:6][cH:7][c:8]([CH:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[c:15]2[cH:16][c:17]([Br:18])[cH:19]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:12]1[CH2:11][CH2:10][CH:9]([c:8]2[cH:7][nH:6][c:5]3[c:4]([C:2]([NH2:1])=[O:3])[cH:19][c:17]([Br:18])[cH:16][c:15]32)[CH2:14][CH2:13]1>C1COCCO1.CO.Cl>[NH2:1][C:2](=[O:3])[c:4]1[c:5]2[nH:6][cH:7][c:8]([CH:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[c:15]2[cH:16][c:17]([Br:18])[cH:19]1\"}",
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},
"smiles": "CC(C)(C)OC(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(Br)cc23)CC1",
"reactionStepId": "sa_1176a9c8de15a5a70000e7dd",
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"metadata": "{\"annotations\":{\"ID\":\"US20090143372A1;0982;719316\",\"rsmi\":\"[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]=[C:11]([c:12]2[cH:13][nH:14][c:15]3[c:16]([C:17]([NH2:18])=[O:19])[cH:20][c:21]([Br:22])[cH:23][c:24]23)[CH2:25][CH2:26]1>CCO.O=[Pt]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([c:12]2[cH:13][nH:14][c:15]3[c:16]([C:17]([NH2:18])=[O:19])[cH:20][c:21]([Br:22])[cH:23][c:24]23)[CH2:25][CH2:26]1\"},\"mapped_reaction_smiles\":\"[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]=[C:11]([c:12]2[cH:13][nH:14][c:15]3[c:16]([C:17]([NH2:18])=[O:19])[cH:20][c:21]([Br:22])[cH:23][c:24]23)[CH2:25][CH2:26]1>CCO.O=[Pt]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([c:12]2[cH:13][nH:14][c:15]3[c:16]([C:17]([NH2:18])=[O:19])[cH:20][c:21]([Br:22])[cH:23][c:24]23)[CH2:25][CH2:26]1\"}",
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"children": [
{
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"smiles": "CC(C)(C)OC(=O)N1CC=C(c2c[nH]c3c(C(N)=O)cc(Br)cc23)CC1"
},
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"reactionStepId": null,
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}
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]
},
{
"id": "13321",
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"molecule": {
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"inchikey": "FRYHCSODNHYDPU-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)Cl"
},
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}
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]
}
]
}
}