Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)C1(Oc2ccc(NC(=O)C(C3CCCCC3)n3c(-c4ccc(Cl)cc4)nc4cc(F)c(F)cc43)c(F)c2)CC1
InChiKey
QMBCLOJRFBEBBV-UHFFFAOYSA-N
Route Signature
346cf6c908c133966e5defb8c56bd4c55f316c008e8ef460706dc9dd7f1112e6
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_d73c5e8ffd1855009951f169",
"signature": "346cf6c908c133966e5defb8c56bd4c55f316c008e8ef460706dc9dd7f1112e6",
"contentHash": "6abfd349bd3670ed1162e4c9e9e65dba37d5f2baf353fddf1ad0329f2b90fd2c",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_be2cb4895f17b7e964823b75",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01958",
"moleculeId": "sa_d1625ccd7f4df2513e71c2f7",
"smiles": "COC(=O)C1(Oc2ccc(NC(=O)C(C3CCCCC3)n3c(-c4ccc(Cl)cc4)nc4cc(F)c(F)cc43)c(F)c2)CC1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_d1625ccd7f4df2513e71c2f7",
"inchikey": "QMBCLOJRFBEBBV-UHFFFAOYSA-N",
"smiles": "COC(=O)C1(Oc2ccc(NC(=O)C(C3CCCCC3)n3c(-c4ccc(Cl)cc4)nc4cc(F)c(F)cc43)c(F)c2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10529",
"routeId": "sa_d73c5e8ffd1855009951f169",
"moleculeId": "sa_d1625ccd7f4df2513e71c2f7",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_d1625ccd7f4df2513e71c2f7",
"inchikey": "QMBCLOJRFBEBBV-UHFFFAOYSA-N",
"smiles": "COC(=O)C1(Oc2ccc(NC(=O)C(C3CCCCC3)n3c(-c4ccc(Cl)cc4)nc4cc(F)c(F)cc43)c(F)c2)CC1"
},
"smiles": "COC(=O)C1(Oc2ccc(NC(=O)C(C3CCCCC3)n3c(-c4ccc(Cl)cc4)nc4cc(F)c(F)cc43)c(F)c2)CC1",
"reactionStepId": "sa_d9dd489f42ed9e3e25f5c982",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090163552A1;0444;729063\",\"rsmi\":\"O=[C:13]([OH:14])[CH:15]([CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[n:22]1[c:23](-[c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]2)[n:31][c:32]2[c:33]1[cH:34][c:35]([F:36])[c:37]([F:38])[cH:39]2.[CH3:1][O:2][C:3](=[O:4])[C:5]1([O:6][c:7]2[cH:8][c:9]([F:10])[c:11]([NH2:12])[cH:40][cH:41]2)[CH2:42][CH2:43]1>CCOC(=O)c1ccc(NC(=O)C(C2CCCCC2)n2c(-c3ccc(Cl)cc3)nc3cc(F)c(F)cc32)cc1.CN(C)c1ccncc1>[CH3:1][O:2][C:3](=[O:4])[C:5]1([O:6][c:7]2[cH:8][c:9]([F:10])[c:11]([NH:12][C:13](=[O:14])[CH:15]([CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[n:22]3[c:23](-[c:24]4[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]4)[n:31][c:32]4[c:33]3[cH:34][c:35]([F:36])[c:37]([F:38])[cH:39]4)[cH:40][cH:41]2)[CH2:42][CH2:43]1\"},\"mapped_reaction_smiles\":\"O=[C:13]([OH:14])[CH:15]([CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[n:22]1[c:23](-[c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]2)[n:31][c:32]2[c:33]1[cH:34][c:35]([F:36])[c:37]([F:38])[cH:39]2.[CH3:1][O:2][C:3](=[O:4])[C:5]1([O:6][c:7]2[cH:8][c:9]([F:10])[c:11]([NH2:12])[cH:40][cH:41]2)[CH2:42][CH2:43]1>CCOC(=O)c1ccc(NC(=O)C(C2CCCCC2)n2c(-c3ccc(Cl)cc3)nc3cc(F)c(F)cc32)cc1.CN(C)c1ccncc1>[CH3:1][O:2][C:3](=[O:4])[C:5]1([O:6][c:7]2[cH:8][c:9]([F:10])[c:11]([NH:12][C:13](=[O:14])[CH:15]([CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[n:22]3[c:23](-[c:24]4[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]4)[n:31][c:32]4[c:33]3[cH:34][c:35]([F:36])[c:37]([F:38])[cH:39]4)[cH:40][cH:41]2)[CH2:42][CH2:43]1\"}",
"reactionStep": {
"id": "sa_d9dd489f42ed9e3e25f5c982",
"reactionHash": "43ac1668456528614b2299c4d040ad50ce0e084621e98dd200e3181f0c93b4be"
},
"children": [
{
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"routeId": "sa_d73c5e8ffd1855009951f169",
"moleculeId": "sa_46b93c1563edd926500067f5",
"parentId": "10529",
"isLeaf": false,
"molecule": {
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"inchikey": "BXXGLEDCMRJQBE-UHFFFAOYSA-N",
"smiles": "COC(=O)C1(Oc2ccc(N)c(F)c2)CC1"
},
"smiles": "COC(=O)C1(Oc2ccc(N)c(F)c2)CC1",
"reactionStepId": "sa_2b0a74a4fc73d72b6184f14e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090163552A1;0482;729068\",\"rsmi\":\"O=[N+:12]([O-])[c:11]1[c:9]([F:10])[cH:8][c:7]([O:6][C:5]2([C:3]([O:2][CH3:1])=[O:4])[CH2:15][CH2:16]2)[cH:14][cH:13]1>CCO.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:4])[C:5]1([O:6][c:7]2[cH:8][c:9]([F:10])[c:11]([NH2:12])[cH:13][cH:14]2)[CH2:15][CH2:16]1\"},\"mapped_reaction_smiles\":\"O=[N+:12]([O-])[c:11]1[c:9]([F:10])[cH:8][c:7]([O:6][C:5]2([C:3]([O:2][CH3:1])=[O:4])[CH2:15][CH2:16]2)[cH:14][cH:13]1>CCO.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:4])[C:5]1([O:6][c:7]2[cH:8][c:9]([F:10])[c:11]([NH2:12])[cH:13][cH:14]2)[CH2:15][CH2:16]1\"}",
"reactionStep": {
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"reactionHash": "e659093fa32d64e7ba4dfc2033ae70c78cff3b097c7d7c132e87a441628a9251"
},
"children": [
{
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"routeId": "sa_d73c5e8ffd1855009951f169",
"moleculeId": "sa_3e62d6dee555bf0b892300f1",
"parentId": "10530",
"isLeaf": false,
"molecule": {
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"inchikey": "NVWCIGLTVLTELZ-UHFFFAOYSA-N",
"smiles": "COC(=O)C1(Oc2ccc([N+](=O)[O-])c(F)c2)CC1"
},
"smiles": "COC(=O)C1(Oc2ccc([N+](=O)[O-])c(F)c2)CC1",
"reactionStepId": "sa_ca969c42b27e1eebf0090568",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090163552A1;0484;729069\",\"rsmi\":\"Br[CH2:18][CH2:17][CH:5]([C:3]([O:2][CH3:1])=[O:4])[O:6][c:7]1[cH:8][c:9]([F:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1>C1CCOC1.CC(C)(C)O.[K+]>[CH3:1][O:2][C:3](=[O:4])[C:5]1([O:6][c:7]2[cH:8][c:9]([F:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[CH2:17][CH2:18]1\"},\"mapped_reaction_smiles\":\"Br[CH2:18][CH2:17][CH:5]([C:3]([O:2][CH3:1])=[O:4])[O:6][c:7]1[cH:8][c:9]([F:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1>C1CCOC1.CC(C)(C)O.[K+]>[CH3:1][O:2][C:3](=[O:4])[C:5]1([O:6][c:7]2[cH:8][c:9]([F:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[CH2:17][CH2:18]1\"}",
"reactionStep": {
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"reactionHash": "65b9aeba4b23ad3aec29bba70ab223468507479032056f5601f749697f10d0fe"
},
"children": [
{
"id": "10532",
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"moleculeId": "sa_25654b88a47bfe6363fc3ede",
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"molecule": {
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"inchikey": "FXOMOISWPYRUEK-UHFFFAOYSA-N",
"smiles": "COC(=O)C(CCBr)Oc1ccc([N+](=O)[O-])c(F)c1"
},
"smiles": "COC(=O)C(CCBr)Oc1ccc([N+](=O)[O-])c(F)c1",
"reactionStepId": "sa_412736d53e10c5301949efc9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090163552A1;0486;729070\",\"rsmi\":\"Br[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7][Br:8].[OH:9][c:10]1[cH:11][c:12]([F:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1>CN(C)C=O.Cl.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][CH2:7][Br:8])[O:9][c:10]1[cH:11][c:12]([F:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"Br[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7][Br:8].[OH:9][c:10]1[cH:11][c:12]([F:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1>CN(C)C=O.Cl.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][CH2:7][Br:8])[O:9][c:10]1[cH:11][c:12]([F:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1\"}",
"reactionStep": {
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"children": [
{
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"smiles": "O=[N+]([O-])c1ccc(O)cc1F"
},
"smiles": "O=[N+]([O-])c1ccc(O)cc1F",
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"metadata": null,
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},
{
"id": "10534",
"routeId": "sa_d73c5e8ffd1855009951f169",
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"parentId": "10532",
"isLeaf": true,
"molecule": {
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"inchikey": "DQHIGEQXJBMKKY-UHFFFAOYSA-N",
"smiles": "COC(=O)C(Br)CCBr"
},
"smiles": "COC(=O)C(Br)CCBr",
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}
]
}
]
}
]
},
{
"id": "10535",
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"moleculeId": "sa_693099df6157e4de3705cb9a",
"parentId": "10529",
"isLeaf": false,
"molecule": {
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"inchikey": "MFXYNLTUXVTKFS-UHFFFAOYSA-N",
"smiles": "O=C(O)C(C1CCCCC1)n1c(-c2ccc(Cl)cc2)nc2cc(F)c(F)cc21"
},
"smiles": "O=C(O)C(C1CCCCC1)n1c(-c2ccc(Cl)cc2)nc2cc(F)c(F)cc21",
"reactionStepId": "sa_a7767dc809b1527012edadb3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090163552A1;0307;729036\",\"rsmi\":\"CC[O:3][C:2](=[O:1])[CH:4]([CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)[n:11]1[c:12](-[c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[n:20][c:21]2[c:22]1[cH:23][c:24]([F:25])[c:26]([F:27])[cH:28]2>C1COCCO1.O.O.[Li+].O>[O:1]=[C:2]([OH:3])[CH:4]([CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)[n:11]1[c:12](-[c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[n:20][c:21]2[c:22]1[cH:23][c:24]([F:25])[c:26]([F:27])[cH:28]2\"},\"mapped_reaction_smiles\":\"CC[O:3][C:2](=[O:1])[CH:4]([CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)[n:11]1[c:12](-[c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[n:20][c:21]2[c:22]1[cH:23][c:24]([F:25])[c:26]([F:27])[cH:28]2>C1COCCO1.O.O.[Li+].O>[O:1]=[C:2]([OH:3])[CH:4]([CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)[n:11]1[c:12](-[c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[n:20][c:21]2[c:22]1[cH:23][c:24]([F:25])[c:26]([F:27])[cH:28]2\"}",
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"molecule": {
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"reactionStepId": "sa_f9c5f42ed94fba9ea51d47ed",
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{
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{
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},
"smiles": "Fc1cc2nc(-c3ccc(Cl)cc3)[nH]c2cc1F",
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"metadata": "{\"annotations\":{\"ID\":\"US20090163552A1;0305;729034\",\"rsmi\":\"O=[C:10](O)[c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1.[F:1][c:2]1[cH:3][c:4]([NH2:18])[c:5]([NH2:9])[cH:6][c:7]1[F:8]>CCOC(C)=O.O>[F:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[F:8])[nH:9][c:10](-[c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1)[n:18]2\"},\"mapped_reaction_smiles\":\"O=[C:10](O)[c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1.[F:1][c:2]1[cH:3][c:4]([NH2:18])[c:5]([NH2:9])[cH:6][c:7]1[F:8]>CCOC(C)=O.O>[F:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[F:8])[nH:9][c:10](-[c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1)[n:18]2\"}",
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