Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COCCOc1cnccc1-c1cn(C)c(=O)c2cc(CN3CCN(S(C)(=O)=O)C[C@H]3C)oc12
InChiKey
HODLGFLRFMOVJV-MRXNPFEDSA-N
Route Signature
20e4e65be08991d65cb822f307946c175d53627f89209503890f156cc8c8115a
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_110242e9a763f049900b2dc6",
"signature": "20e4e65be08991d65cb822f307946c175d53627f89209503890f156cc8c8115a",
"contentHash": "74d2b2683efb392acc0c0a3289e48ee2af3b217b583cfe7b4fdb75368e2f5bbb",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_73523ebe602831b5789e650f",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01620",
"moleculeId": "sa_ae4977dcfdb4340ea1d6749f",
"smiles": "COCCOc1cnccc1-c1cn(C)c(=O)c2cc(CN3CCN(S(C)(=O)=O)C[C@H]3C)oc12",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_ae4977dcfdb4340ea1d6749f",
"inchikey": "HODLGFLRFMOVJV-MRXNPFEDSA-N",
"smiles": "COCCOc1cnccc1-c1cn(C)c(=O)c2cc(CN3CCN(S(C)(=O)=O)C[C@H]3C)oc12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10341",
"routeId": "sa_110242e9a763f049900b2dc6",
"moleculeId": "sa_ae4977dcfdb4340ea1d6749f",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_ae4977dcfdb4340ea1d6749f",
"inchikey": "HODLGFLRFMOVJV-MRXNPFEDSA-N",
"smiles": "COCCOc1cnccc1-c1cn(C)c(=O)c2cc(CN3CCN(S(C)(=O)=O)C[C@H]3C)oc12"
},
"smiles": "COCCOc1cnccc1-c1cn(C)c(=O)c2cc(CN3CCN(S(C)(=O)=O)C[C@H]3C)oc12",
"reactionStepId": "sa_f09be17b0542c4a199b7bdbe",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016966A1;0640;1824391\",\"rsmi\":\"Br[c:8]1[cH:9][n:10]([CH3:11])[c:12](=[O:13])[c:14]2[c:15]1[o:16][c:17]([CH2:18][N:19]1[CH2:20][CH2:21][N:22]([S:23]([CH3:24])(=[O:25])=[O:26])[CH2:27][C@H:28]1[CH3:29])[cH:30]2.CC1(C)OB([c:7]2[c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:34][n:33][cH:32][cH:31]2)OC1(C)C>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[c:7](-[c:8]2[cH:9][n:10]([CH3:11])[c:12](=[O:13])[c:14]3[c:15]2[o:16][c:17]([CH2:18][N:19]2[CH2:20][CH2:21][N:22]([S:23]([CH3:24])(=[O:25])=[O:26])[CH2:27][C@H:28]2[CH3:29])[cH:30]3)[cH:31][cH:32][n:33][cH:34]1\"},\"mapped_reaction_smiles\":\"Br[c:8]1[cH:9][n:10]([CH3:11])[c:12](=[O:13])[c:14]2[c:15]1[o:16][c:17]([CH2:18][N:19]1[CH2:20][CH2:21][N:22]([S:23]([CH3:24])(=[O:25])=[O:26])[CH2:27][C@H:28]1[CH3:29])[cH:30]2.CC1(C)OB([c:7]2[c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:34][n:33][cH:32][cH:31]2)OC1(C)C>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[c:7](-[c:8]2[cH:9][n:10]([CH3:11])[c:12](=[O:13])[c:14]3[c:15]2[o:16][c:17]([CH2:18][N:19]2[CH2:20][CH2:21][N:22]([S:23]([CH3:24])(=[O:25])=[O:26])[CH2:27][C@H:28]2[CH3:29])[cH:30]3)[cH:31][cH:32][n:33][cH:34]1\"}",
"reactionStep": {
"id": "sa_f09be17b0542c4a199b7bdbe",
"reactionHash": "7be50df1657dccc3a22da671012c5614b724f9cdbd2eeb7b8240f3e3d8c882fc"
},
"children": [
{
"id": "10342",
"routeId": "sa_110242e9a763f049900b2dc6",
"moleculeId": "sa_ef6235b02ee2e95ed16896c5",
"parentId": "10341",
"isLeaf": true,
"molecule": {
"id": "sa_ef6235b02ee2e95ed16896c5",
"inchikey": "AETWBQNDEJWZTI-UHFFFAOYSA-N",
"smiles": "COCCOc1cnccc1B1OC(C)(C)C(C)(C)O1"
},
"smiles": "COCCOc1cnccc1B1OC(C)(C)C(C)(C)O1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10343",
"routeId": "sa_110242e9a763f049900b2dc6",
"moleculeId": "sa_9617e8feb6bc2336c1e02344",
"parentId": "10341",
"isLeaf": false,
"molecule": {
"id": "sa_9617e8feb6bc2336c1e02344",
"inchikey": "YFGAENDDPLUACK-SNVBAGLBSA-N",
"smiles": "C[C@@H]1CN(S(C)(=O)=O)CCN1Cc1cc2c(=O)n(C)cc(Br)c2o1"
},
"smiles": "C[C@@H]1CN(S(C)(=O)=O)CCN1Cc1cc2c(=O)n(C)cc(Br)c2o1",
"reactionStepId": "sa_af0b1fa5e240b25dc5710f5a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016966A1;0443;1824279\",\"rsmi\":\"O=[CH:12][c:13]1[cH:14][c:15]2[c:16]([o:17]1)[c:18]([Br:19])[cH:20][n:21]([CH3:22])[c:23]2=[O:24].[CH3:1][C@@H:2]1[CH2:3][N:4]([S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][CH2:10][NH:11]1>CC(=O)O.CO>[CH3:1][C@@H:2]1[CH2:3][N:4]([S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][CH2:10][N:11]1[CH2:12][c:13]1[cH:14][c:15]2[c:16]([o:17]1)[c:18]([Br:19])[cH:20][n:21]([CH3:22])[c:23]2=[O:24]\"},\"mapped_reaction_smiles\":\"O=[CH:12][c:13]1[cH:14][c:15]2[c:16]([o:17]1)[c:18]([Br:19])[cH:20][n:21]([CH3:22])[c:23]2=[O:24].[CH3:1][C@@H:2]1[CH2:3][N:4]([S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][CH2:10][NH:11]1>CC(=O)O.CO>[CH3:1][C@@H:2]1[CH2:3][N:4]([S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][CH2:10][N:11]1[CH2:12][c:13]1[cH:14][c:15]2[c:16]([o:17]1)[c:18]([Br:19])[cH:20][n:21]([CH3:22])[c:23]2=[O:24]\"}",
"reactionStep": {
"id": "sa_af0b1fa5e240b25dc5710f5a",
"reactionHash": "e672aa97851313ab9d359a2a19336c04b4d84780b813b334475e084881d11d47"
},
"children": [
{
"id": "10344",
"routeId": "sa_110242e9a763f049900b2dc6",
"moleculeId": "sa_de585f68ea0d7c6cb82fe8db",
"parentId": "10343",
"isLeaf": false,
"molecule": {
"id": "sa_de585f68ea0d7c6cb82fe8db",
"inchikey": "AHXSBNBPHMFXGQ-ZCFIWIBFSA-N",
"smiles": "C[C@@H]1CN(S(C)(=O)=O)CCN1"
},
"smiles": "C[C@@H]1CN(S(C)(=O)=O)CCN1",
"reactionStepId": "sa_3f6d4b8c12c59c4be25e3c0e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016966A1;0439;1824276\",\"rsmi\":\"Cl[S:5]([CH3:6])(=[O:7])=[O:8].[CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:9][CH2:10][NH:11]1>C1CCOC1.Cl.[Na+].O>[CH3:1][C@@H:2]1[CH2:3][N:4]([S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][CH2:10][NH:11]1\"},\"mapped_reaction_smiles\":\"Cl[S:5]([CH3:6])(=[O:7])=[O:8].[CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:9][CH2:10][NH:11]1>C1CCOC1.Cl.[Na+].O>[CH3:1][C@@H:2]1[CH2:3][N:4]([S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][CH2:10][NH:11]1\"}",
"reactionStep": {
"id": "sa_3f6d4b8c12c59c4be25e3c0e",
"reactionHash": "1756dc3a89f5f7d82f0a7cd680d225d238a78e7888a3c146e9e41cb671a9dc66"
},
"children": [
{
"id": "10345",
"routeId": "sa_110242e9a763f049900b2dc6",
"moleculeId": "sa_4414747174e65ec33d87d739",
"parentId": "10344",
"isLeaf": true,
"molecule": {
"id": "sa_4414747174e65ec33d87d739",
"inchikey": "JOMNTHCQHJPVAZ-RXMQYKEDSA-N",
"smiles": "C[C@@H]1CNCCN1"
},
"smiles": "C[C@@H]1CNCCN1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10346",
"routeId": "sa_110242e9a763f049900b2dc6",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "10344",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10347",
"routeId": "sa_110242e9a763f049900b2dc6",
"moleculeId": "sa_a7905762374b8deb65066a88",
"parentId": "10343",
"isLeaf": false,
"molecule": {
"id": "sa_a7905762374b8deb65066a88",
"inchikey": "XKFNMNHUUDOEHY-UHFFFAOYSA-N",
"smiles": "Cn1cc(Br)c2oc(C=O)cc2c1=O"
},
"smiles": "Cn1cc(Br)c2oc(C=O)cc2c1=O",
"reactionStepId": "sa_9509239bf41ded0d5d5fe1ee",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016966A1;0437;1824274\",\"rsmi\":\"I[CH3:1].[nH:2]1[cH:3][c:4]([Br:5])[c:6]2[c:7]([cH:8][c:9]([CH:10]=[O:11])[o:12]2)[c:13]1=[O:14]>C1CCOC1.O=C(O)O.[Cs+].[Cs+]>[CH3:1][n:2]1[cH:3][c:4]([Br:5])[c:6]2[c:7]([cH:8][c:9]([CH:10]=[O:11])[o:12]2)[c:13]1=[O:14]\"},\"mapped_reaction_smiles\":\"I[CH3:1].[nH:2]1[cH:3][c:4]([Br:5])[c:6]2[c:7]([cH:8][c:9]([CH:10]=[O:11])[o:12]2)[c:13]1=[O:14]>C1CCOC1.O=C(O)O.[Cs+].[Cs+]>[CH3:1][n:2]1[cH:3][c:4]([Br:5])[c:6]2[c:7]([cH:8][c:9]([CH:10]=[O:11])[o:12]2)[c:13]1=[O:14]\"}",
"reactionStep": {
"id": "sa_9509239bf41ded0d5d5fe1ee",
"reactionHash": "9f672fbed4ac2a12b5a7abbf10ee800023f00859befa480e1016d260e8014174"
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"children": [
{
"id": "10348",
"routeId": "sa_110242e9a763f049900b2dc6",
"moleculeId": "sa_b7567a1345cf70214cab50f4",
"parentId": "10347",
"isLeaf": true,
"molecule": {
"id": "sa_b7567a1345cf70214cab50f4",
"inchikey": "FUTNRFCTJWUVSJ-UHFFFAOYSA-N",
"smiles": "O=Cc1cc2c(=O)[nH]cc(Br)c2o1"
},
"smiles": "O=Cc1cc2c(=O)[nH]cc(Br)c2o1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10349",
"routeId": "sa_110242e9a763f049900b2dc6",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
"parentId": "10347",
"isLeaf": true,
"molecule": {
"id": "sa_82fdccf7d1cc329c9db73f21",
"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}