Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(CCCn1cnc2c[n+]([O-])c3ccccc3c21)c1ccccc1
InChiKey
XAMMLGUXXDTAQJ-UHFFFAOYSA-N
Route Signature
9436fc5b6023b846cd5357571e2e08989256d78fd8c44548722487929e1af6dd
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_70260c6ec3b03e0f6620b2f1",
"signature": "9436fc5b6023b846cd5357571e2e08989256d78fd8c44548722487929e1af6dd",
"contentHash": "699a98df90fa90b53cb32b22da0bbe851a8ac46b9b7dea7195525776ea541ad5",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_8107aa3e14a0e3f72db6e7cf",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00083",
"moleculeId": "sa_ebfef8dc58264c54f9ff0ed4",
"smiles": "O=C(CCCn1cnc2c[n+]([O-])c3ccccc3c21)c1ccccc1",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_ebfef8dc58264c54f9ff0ed4",
"inchikey": "XAMMLGUXXDTAQJ-UHFFFAOYSA-N",
"smiles": "O=C(CCCn1cnc2c[n+]([O-])c3ccccc3c21)c1ccccc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12365",
"routeId": "sa_70260c6ec3b03e0f6620b2f1",
"moleculeId": "sa_ebfef8dc58264c54f9ff0ed4",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_ebfef8dc58264c54f9ff0ed4",
"inchikey": "XAMMLGUXXDTAQJ-UHFFFAOYSA-N",
"smiles": "O=C(CCCn1cnc2c[n+]([O-])c3ccccc3c21)c1ccccc1"
},
"smiles": "O=C(CCCn1cnc2c[n+]([O-])c3ccccc3c21)c1ccccc1",
"reactionStepId": "sa_1c5c5e20a68448c37d5dbae3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140194628A1;1117;1549203\",\"rsmi\":\"O=C(O[OH:18])c1cccc(Cl)c1.[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:19]2)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n+:17]([O-:18])[cH:19]2)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1\"},\"mapped_reaction_smiles\":\"O=C(O[OH:18])c1cccc(Cl)c1.[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:19]2)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n+:17]([O-:18])[cH:19]2)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1\"}",
"reactionStep": {
"id": "sa_1c5c5e20a68448c37d5dbae3",
"reactionHash": "4b5c4db2bb904f33a562e3eed659cfabc78658b938bf063983a6021c2faae6bf"
},
"children": [
{
"id": "12366",
"routeId": "sa_70260c6ec3b03e0f6620b2f1",
"moleculeId": "sa_292aab804b3670e84ce954f3",
"parentId": "12365",
"isLeaf": true,
"molecule": {
"id": "sa_292aab804b3670e84ce954f3",
"inchikey": "NHQDETIJWKXCTC-UHFFFAOYSA-N",
"smiles": "O=C(OO)c1cccc(Cl)c1"
},
"smiles": "O=C(OO)c1cccc(Cl)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12367",
"routeId": "sa_70260c6ec3b03e0f6620b2f1",
"moleculeId": "sa_a6bfd848280d2b3499773e20",
"parentId": "12365",
"isLeaf": false,
"molecule": {
"id": "sa_a6bfd848280d2b3499773e20",
"inchikey": "OATLNRKXTGPMBT-UHFFFAOYSA-N",
"smiles": "O=C(CCCn1cnc2cnc3ccccc3c21)c1ccccc1"
},
"smiles": "O=C(CCCn1cnc2cnc3ccccc3c21)c1ccccc1",
"reactionStepId": "sa_a4b47acaf5c2c6626f68d079",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140194628A1;1115;1549202\",\"rsmi\":\"[OH:1][CH:2]([CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>CCN(CC)CC.CS(C)=O.O=C(Cl)C(=O)Cl>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"[OH:1][CH:2]([CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>CCN(CC)CC.CS(C)=O.O=C(Cl)C(=O)Cl>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_a4b47acaf5c2c6626f68d079",
"reactionHash": "d0751c287f968cc6521024ce4aa31cf841f0a930d96c2a68db657a588bda86b3"
},
"children": [
{
"id": "12368",
"routeId": "sa_70260c6ec3b03e0f6620b2f1",
"moleculeId": "sa_a180a4c0b0f43d5a378b4055",
"parentId": "12367",
"isLeaf": false,
"molecule": {
"id": "sa_a180a4c0b0f43d5a378b4055",
"inchikey": "AAVHDZYYUFZSSB-UHFFFAOYSA-N",
"smiles": "OC(CCCn1cnc2cnc3ccccc3c21)c1ccccc1"
},
"smiles": "OC(CCCn1cnc2cnc3ccccc3c21)c1ccccc1",
"reactionStepId": "sa_f58283a5dc8d626c25b82f05",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140194628A1;1113;1549201\",\"rsmi\":\"Br[Mg][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2>C1CCOC1>[OH:1][CH:2]([CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"Br[Mg][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2>C1CCOC1>[OH:1][CH:2]([CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_f58283a5dc8d626c25b82f05",
"reactionHash": "b8c4239136b1ac772978dc9c28c7a179dbda461f6fce9403c274f000935d82c2"
},
"children": [
{
"id": "12369",
"routeId": "sa_70260c6ec3b03e0f6620b2f1",
"moleculeId": "sa_eea5395d54e06a9c4a79ce0d",
"parentId": "12368",
"isLeaf": true,
"molecule": {
"id": "sa_eea5395d54e06a9c4a79ce0d",
"inchikey": "ANRQGKOBLBYXFM-UHFFFAOYSA-M",
"smiles": "[Br][Mg][c]1ccccc1"
},
"smiles": "[Br][Mg][c]1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12370",
"routeId": "sa_70260c6ec3b03e0f6620b2f1",
"moleculeId": "sa_243559f3f1716d4091bb6db8",
"parentId": "12368",
"isLeaf": false,
"molecule": {
"id": "sa_243559f3f1716d4091bb6db8",
"inchikey": "DKOMSEMLIRMWHS-UHFFFAOYSA-N",
"smiles": "O=CCCCn1cnc2cnc3ccccc3c21"
},
"smiles": "O=CCCCn1cnc2cnc3ccccc3c21",
"reactionStepId": "sa_32f2d78d5313eb9e7dfde3f2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140194628A1;1111;1549200\",\"rsmi\":\"[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2>CCN(CC)CC.CS(C)=O.O=C(Cl)C(=O)Cl>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2\"},\"mapped_reaction_smiles\":\"[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2>CCN(CC)CC.CS(C)=O.O=C(Cl)C(=O)Cl>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2\"}",
"reactionStep": {
"id": "sa_32f2d78d5313eb9e7dfde3f2",
"reactionHash": "6b6f6a1b76bc3c26d97bf2e1e7ea4a7827328b2254f098a650e09dbc3c47b7c2"
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"children": [
{
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"moleculeId": "sa_6b8b980327876668cfa3cc12",
"parentId": "12370",
"isLeaf": false,
"molecule": {
"id": "sa_6b8b980327876668cfa3cc12",
"inchikey": "VVRQJMIECSNSCA-UHFFFAOYSA-N",
"smiles": "OCCCCn1cnc2cnc3ccccc3c21"
},
"smiles": "OCCCCn1cnc2cnc3ccccc3c21",
"reactionStepId": "sa_3b45f96ed75b66e44d1a7d92",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140194628A1;1109;1549199\",\"rsmi\":\"CC(C)(C)[Si](C)(C)[O:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.F>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2\"},\"mapped_reaction_smiles\":\"CC(C)(C)[Si](C)(C)[O:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.F>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11]1[c:12]([cH:13][cH:14][cH:15][cH:16]1)[n:17][cH:18]2\"}",
"reactionStep": {
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"reactionHash": "321277bc110e324356db8b31406e80ce8c65eba8360c1af92caaf1ee9d83a402"
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"children": [
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"parentId": "12371",
"isLeaf": false,
"molecule": {
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"inchikey": "KANPKGTVRMNJQQ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCCCn1cnc2cnc3ccccc3c21"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCCCn1cnc2cnc3ccccc3c21",
"reactionStepId": "sa_928a3a4e6d746c2090e45cc0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140194628A1;1107;1549198\",\"rsmi\":\"CCO[CH:14](OCC)OCC.[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][c:17]1[c:16]([NH2:15])[cH:25][n:24][c:19]2[c:18]1[cH:23][cH:22][cH:21][cH:20]2>Cc1ccccc1>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][n:13]1[cH:14][n:15][c:16]2[c:17]1[c:18]1[c:19]([cH:20][cH:21][cH:22][cH:23]1)[n:24][cH:25]2\"},\"mapped_reaction_smiles\":\"CCO[CH:14](OCC)OCC.[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][c:17]1[c:16]([NH2:15])[cH:25][n:24][c:19]2[c:18]1[cH:23][cH:22][cH:21][cH:20]2>Cc1ccccc1>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][n:13]1[cH:14][n:15][c:16]2[c:17]1[c:18]1[c:19]([cH:20][cH:21][cH:22][cH:23]1)[n:24][cH:25]2\"}",
"reactionStep": {
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"reactionHash": "78d6d86923288814ff309585261ecd5819a180fc2ee01f59d7f5b7f4ed080a73"
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"children": [
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"moleculeId": "sa_dc98236d967ab0cdbd0fcd04",
"parentId": "12372",
"isLeaf": true,
"molecule": {
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"smiles": "CCOC(OCC)OCC"
},
"smiles": "CCOC(OCC)OCC",
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{
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"inchikey": "SFJMIDVSYZQCML-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCCCNc1c(N)cnc2ccccc12"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCCCNc1c(N)cnc2ccccc12",
"reactionStepId": "sa_24d1aa7794c3977e50b82c31",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140194628A1;1077;1549187\",\"rsmi\":\"O=[N+:16]([O-])[c:15]1[c:14]([NH:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[c:24]2[c:19]([n:18][cH:17]1)[cH:20][cH:21][cH:22][cH:23]2>CC(C)(C)[Si](C)(C)O.Cc1ccccc1.[H][H].[Pt]>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][c:14]1[c:15]([NH2:16])[cH:17][n:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12\"},\"mapped_reaction_smiles\":\"O=[N+:16]([O-])[c:15]1[c:14]([NH:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[c:24]2[c:19]([n:18][cH:17]1)[cH:20][cH:21][cH:22][cH:23]2>CC(C)(C)[Si](C)(C)O.Cc1ccccc1.[H][H].[Pt]>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][c:14]1[c:15]([NH2:16])[cH:17][n:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12\"}",
"reactionStep": {
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"children": [
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"moleculeId": "sa_960a099ee19da4b51b65ac6b",
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"molecule": {
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"inchikey": "OZLZNFISKAPDQT-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCCCNc1c([N+](=O)[O-])cnc2ccccc12"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCCCNc1c([N+](=O)[O-])cnc2ccccc12",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
]
}
]
}
]
}
]
}
}