Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)(C)OC(=O)N1CC(O)CC(CNc2nc(-c3ccc(N4CCOCC4)cc3)cc3nccnc23)C1
InChiKey
VNKQSKZAMIOWAW-UHFFFAOYSA-N
Route Signature
b27996706465f7d7c43d76f908d6d62fe14d89b628e9c395db8a522e24f57232
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_a7d86e089670ee0bb9da8aad",
"signature": "b27996706465f7d7c43d76f908d6d62fe14d89b628e9c395db8a522e24f57232",
"contentHash": "36fc26912c6e5546586a27ec0fa7427a9c60b77056fec78e3d5310f54c768937",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_b6275e7873e6c8515394c56b",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00249",
"moleculeId": "sa_dc7183fb193785d3b43f0250",
"smiles": "CC(C)(C)OC(=O)N1CC(O)CC(CNc2nc(-c3ccc(N4CCOCC4)cc3)cc3nccnc23)C1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_dc7183fb193785d3b43f0250",
"inchikey": "VNKQSKZAMIOWAW-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC(O)CC(CNc2nc(-c3ccc(N4CCOCC4)cc3)cc3nccnc23)C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9317",
"routeId": "sa_a7d86e089670ee0bb9da8aad",
"moleculeId": "sa_dc7183fb193785d3b43f0250",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_dc7183fb193785d3b43f0250",
"inchikey": "VNKQSKZAMIOWAW-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC(O)CC(CNc2nc(-c3ccc(N4CCOCC4)cc3)cc3nccnc23)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CC(O)CC(CNc2nc(-c3ccc(N4CCOCC4)cc3)cc3nccnc23)C1",
"reactionStepId": "sa_e080dac716f7ac9bb7945889",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140121200A1;0410;1518695\",\"rsmi\":\"Cl[c:18]1[n:17][c:16]([NH:15][CH2:14][CH:13]2[CH2:12][CH:10]([OH:11])[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:38]2)[c:37]2[c:32]([cH:31]1)[n:33][cH:34][cH:35][n:36]2.OB(O)[c:19]1[cH:20][cH:21][c:22]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[cH:29][cH:30]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([OH:11])[CH2:12][CH:13]([CH2:14][NH:15][c:16]2[n:17][c:18](-[c:19]3[cH:20][cH:21][c:22]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)[cH:29][cH:30]3)[cH:31][c:32]3[n:33][cH:34][cH:35][n:36][c:37]23)[CH2:38]1\"},\"mapped_reaction_smiles\":\"Cl[c:18]1[n:17][c:16]([NH:15][CH2:14][CH:13]2[CH2:12][CH:10]([OH:11])[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:38]2)[c:37]2[c:32]([cH:31]1)[n:33][cH:34][cH:35][n:36]2.OB(O)[c:19]1[cH:20][cH:21][c:22]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[cH:29][cH:30]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([OH:11])[CH2:12][CH:13]([CH2:14][NH:15][c:16]2[n:17][c:18](-[c:19]3[cH:20][cH:21][c:22]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)[cH:29][cH:30]3)[cH:31][c:32]3[n:33][cH:34][cH:35][n:36][c:37]23)[CH2:38]1\"}",
"reactionStep": {
"id": "sa_e080dac716f7ac9bb7945889",
"reactionHash": "8e2c125dc573ada0bd329fc4ebfe7fac3298ed3c5c430596ed48ba9aa4764fd3"
},
"children": [
{
"id": "9318",
"routeId": "sa_a7d86e089670ee0bb9da8aad",
"moleculeId": "sa_fc677be3fdcea4d506147513",
"parentId": "9317",
"isLeaf": false,
"molecule": {
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"inchikey": "PMVXQHUZRXLACI-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC(O)CC(CNc2nc(Cl)cc3nccnc23)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CC(O)CC(CNc2nc(Cl)cc3nccnc23)C1",
"reactionStepId": "sa_c68df94c4cd35d412fc3e927",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140121200A1;0201;1518605\",\"rsmi\":\"CC(C)(C)[Si](C)(C)[O:11][CH:10]1[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:27][CH:13]([CH2:14][NH:15][c:16]2[n:17][c:18]([Cl:19])[cH:20][c:21]3[n:22][cH:23][cH:24][n:25][c:26]23)[CH2:12]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.F>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([OH:11])[CH2:12][CH:13]([CH2:14][NH:15][c:16]2[n:17][c:18]([Cl:19])[cH:20][c:21]3[n:22][cH:23][cH:24][n:25][c:26]23)[CH2:27]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[Si](C)(C)[O:11][CH:10]1[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:27][CH:13]([CH2:14][NH:15][c:16]2[n:17][c:18]([Cl:19])[cH:20][c:21]3[n:22][cH:23][cH:24][n:25][c:26]23)[CH2:12]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.F>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([OH:11])[CH2:12][CH:13]([CH2:14][NH:15][c:16]2[n:17][c:18]([Cl:19])[cH:20][c:21]3[n:22][cH:23][cH:24][n:25][c:26]23)[CH2:27]1\"}",
"reactionStep": {
"id": "sa_c68df94c4cd35d412fc3e927",
"reactionHash": "1ee6fd09de9b5bc48ae946d2df7c8ca780ac67f6d5f9f83339ad8a7dcba4e5db"
},
"children": [
{
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"routeId": "sa_a7d86e089670ee0bb9da8aad",
"moleculeId": "sa_e82c3cca8a888b729686a258",
"parentId": "9318",
"isLeaf": false,
"molecule": {
"id": "sa_e82c3cca8a888b729686a258",
"inchikey": "UHSOTASWAAUTBD-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC(CNc2nc(Cl)cc3nccnc23)CC(O[Si](C)(C)C(C)(C)C)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CC(CNc2nc(Cl)cc3nccnc23)CC(O[Si](C)(C)C(C)(C)C)C1",
"reactionStepId": "sa_de292bc8ea5b2a9081c1b804",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140121200A1;0200;1518604\",\"rsmi\":\"Cl[c:13]1[n:14][c:15]([Cl:16])[cH:17][c:18]2[n:19][cH:20][cH:21][n:22][c:23]12.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([CH2:11][NH2:12])[CH2:24][CH:25]([O:26][Si:27]([CH3:28])([CH3:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34]1>C1CCOC1.CCN(C(C)C)C(C)C>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([CH2:11][NH:12][c:13]2[n:14][c:15]([Cl:16])[cH:17][c:18]3[n:19][cH:20][cH:21][n:22][c:23]23)[CH2:24][CH:25]([O:26][Si:27]([CH3:28])([CH3:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34]1\"},\"mapped_reaction_smiles\":\"Cl[c:13]1[n:14][c:15]([Cl:16])[cH:17][c:18]2[n:19][cH:20][cH:21][n:22][c:23]12.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([CH2:11][NH2:12])[CH2:24][CH:25]([O:26][Si:27]([CH3:28])([CH3:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34]1>C1CCOC1.CCN(C(C)C)C(C)C>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([CH2:11][NH:12][c:13]2[n:14][c:15]([Cl:16])[cH:17][c:18]3[n:19][cH:20][cH:21][n:22][c:23]23)[CH2:24][CH:25]([O:26][Si:27]([CH3:28])([CH3:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34]1\"}",
"reactionStep": {
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"reactionHash": "5254dac92f69221bd69f920013fafab9240e49715f54287d4482d1ae7cefe9fe"
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"children": [
{
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"routeId": "sa_a7d86e089670ee0bb9da8aad",
"moleculeId": "sa_89dfe8bd804cd266f6e1d778",
"parentId": "9319",
"isLeaf": false,
"molecule": {
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"inchikey": "NVFDDPWQWDPVER-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC(CN)CC(O[Si](C)(C)C(C)(C)C)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CC(CN)CC(O[Si](C)(C)C(C)(C)C)C1",
"reactionStepId": "sa_d22136fd9bbd92d469a9c293",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140121200A1;0199;1518603\",\"rsmi\":\"[N-]=[N+]=[N:12][CH2:11][CH:10]1[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:23][CH:14]([O:15][Si:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:13]1>CCOC(C)=O.[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([CH2:11][NH2:12])[CH2:13][CH:14]([O:15][Si:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]1\"},\"mapped_reaction_smiles\":\"[N-]=[N+]=[N:12][CH2:11][CH:10]1[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:23][CH:14]([O:15][Si:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:13]1>CCOC(C)=O.[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([CH2:11][NH2:12])[CH2:13][CH:14]([O:15][Si:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_67f7d0a21029d0d2733f779b",
"parentId": "9320",
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"molecule": {
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"inchikey": "IIZHJFBRDBLZFG-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC(CN=[N+]=[N-])CC(O[Si](C)(C)C(C)(C)C)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CC(CN=[N+]=[N-])CC(O[Si](C)(C)C(C)(C)C)C1",
"reactionStepId": "sa_d2e3167578714a12b0cdda3d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140121200A1;0198;1518602\",\"rsmi\":\"O[CH2:11][CH:10]1[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:25][CH:16]([O:17][Si:18]([CH3:19])([CH3:20])[C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:15]1.[N-:12]=[N+:13]=[N-:14]>CCCCCC.CCN(CC)CC.CCOC(C)=O.CCOCC.CS(=O)(=O)Cl.ClCCl.[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([CH2:11][N:12]=[N+:13]=[N-:14])[CH2:15][CH:16]([O:17][Si:18]([CH3:19])([CH3:20])[C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25]1\"},\"mapped_reaction_smiles\":\"O[CH2:11][CH:10]1[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:25][CH:16]([O:17][Si:18]([CH3:19])([CH3:20])[C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:15]1.[N-:12]=[N+:13]=[N-:14]>CCCCCC.CCN(CC)CC.CCOC(C)=O.CCOCC.CS(=O)(=O)Cl.ClCCl.[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([CH2:11][N:12]=[N+:13]=[N-:14])[CH2:15][CH:16]([O:17][Si:18]([CH3:19])([CH3:20])[C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25]1\"}",
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"molecule": {
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"inchikey": "IPOAEDZEWFWWSI-UHFFFAOYSA-N",
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},
"smiles": "CC(C)(C)OC(=O)N1CC(CO)CC(O[Si](C)(C)C(C)(C)C)C1",
"reactionStepId": null,
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{
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"smiles": "[N]N=[N-]"
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{
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"molecule": {
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"inchikey": "SNWNPXRUXXCDOM-UHFFFAOYSA-N",
"smiles": "Clc1cc2nccnc2c(Cl)n1"
},
"smiles": "Clc1cc2nccnc2c(Cl)n1",
"reactionStepId": "sa_82a9d296c32528de957cc78f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140121200A1;0147;1518582\",\"rsmi\":\"O=[CH:6][CH:7]=O.[Cl:1][c:2]1[cH:3][c:4]([NH2:5])[c:9]([NH2:8])[c:10]([Cl:11])[n:12]1>CCO.O>[Cl:1][c:2]1[cH:3][c:4]2[n:5][cH:6][cH:7][n:8][c:9]2[c:10]([Cl:11])[n:12]1\"},\"mapped_reaction_smiles\":\"O=[CH:6][CH:7]=O.[Cl:1][c:2]1[cH:3][c:4]([NH2:5])[c:9]([NH2:8])[c:10]([Cl:11])[n:12]1>CCO.O>[Cl:1][c:2]1[cH:3][c:4]2[n:5][cH:6][cH:7][n:8][c:9]2[c:10]([Cl:11])[n:12]1\"}",
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"metadata": "{\"annotations\":{\"ID\":\"US20140121200A1;0146;1518581\",\"rsmi\":\"O=[N+:4]([O-])[c:3]1[c:2]([NH2:1])[cH:10][c:8]([Cl:9])[n:7][c:5]1[Cl:6]>CCO.Cl.O.[Fe]>[NH2:1][c:2]1[c:3]([NH2:4])[c:5]([Cl:6])[n:7][c:8]([Cl:9])[cH:10]1\"},\"mapped_reaction_smiles\":\"O=[N+:4]([O-])[c:3]1[c:2]([NH2:1])[cH:10][c:8]([Cl:9])[n:7][c:5]1[Cl:6]>CCO.Cl.O.[Fe]>[NH2:1][c:2]1[c:3]([NH2:4])[c:5]([Cl:6])[n:7][c:8]([Cl:9])[cH:10]1\"}",
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},
"smiles": "Nc1cc(Cl)nc(Cl)c1[N+](=O)[O-]",
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},
{
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