Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COCCn1nc(C)cc1C(=O)Nc1cc(Oc2ccc3nc(NC(=O)C4CC4)cn3n2)ccc1F
InChiKey
NDEDXJOZRFZSIG-UHFFFAOYSA-N
Route Signature
d593776b78b2a5f3f40bc84cf5f7d8583ed85fcd8a778bfea8ebf973ac7f79a5
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_4c7ee1a737d7377a4d441795",
"signature": "d593776b78b2a5f3f40bc84cf5f7d8583ed85fcd8a778bfea8ebf973ac7f79a5",
"contentHash": "3d69847ea358f60289167ef32302b5f709b41a458b13864482e24a64b2865fb5",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_5e3e99e13157f054734a25ba",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00934",
"moleculeId": "sa_e5398b322306f60cdc54d0fa",
"smiles": "COCCn1nc(C)cc1C(=O)Nc1cc(Oc2ccc3nc(NC(=O)C4CC4)cn3n2)ccc1F",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_e5398b322306f60cdc54d0fa",
"inchikey": "NDEDXJOZRFZSIG-UHFFFAOYSA-N",
"smiles": "COCCn1nc(C)cc1C(=O)Nc1cc(Oc2ccc3nc(NC(=O)C4CC4)cn3n2)ccc1F"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9800",
"routeId": "sa_4c7ee1a737d7377a4d441795",
"moleculeId": "sa_e5398b322306f60cdc54d0fa",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_e5398b322306f60cdc54d0fa",
"inchikey": "NDEDXJOZRFZSIG-UHFFFAOYSA-N",
"smiles": "COCCn1nc(C)cc1C(=O)Nc1cc(Oc2ccc3nc(NC(=O)C4CC4)cn3n2)ccc1F"
},
"smiles": "COCCn1nc(C)cc1C(=O)Nc1cc(Oc2ccc3nc(NC(=O)C4CC4)cn3n2)ccc1F",
"reactionStepId": "sa_fe136b9ed8e4577a53469b17",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100273788A1;1721;965529\",\"rsmi\":\"O[C:11]([c:10]1[n:5]([CH2:4][CH2:3][O:2][CH3:1])[n:6][c:7]([CH3:8])[cH:9]1)=[O:12].[NH2:13][c:14]1[c:15]([F:16])[cH:17][cH:18][c:19]([O:20][c:21]2[n:22][n:23]3[cH:24][c:25]([NH:26][C:27](=[O:28])[CH:29]4[CH2:30][CH2:31]4)[n:32][c:33]3[cH:34][cH:35]2)[cH:36]1>C1CCOC1.CC(=O)N(C)C.CN(C)C=O.O=C(Cl)C(=O)Cl>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[n:6][c:7]([CH3:8])[cH:9][c:10]1[C:11](=[O:12])[NH:13][c:14]1[c:15]([F:16])[cH:17][cH:18][c:19]([O:20][c:21]2[n:22][n:23]3[cH:24][c:25]([NH:26][C:27](=[O:28])[CH:29]4[CH2:30][CH2:31]4)[n:32][c:33]3[cH:34][cH:35]2)[cH:36]1\"},\"mapped_reaction_smiles\":\"O[C:11]([c:10]1[n:5]([CH2:4][CH2:3][O:2][CH3:1])[n:6][c:7]([CH3:8])[cH:9]1)=[O:12].[NH2:13][c:14]1[c:15]([F:16])[cH:17][cH:18][c:19]([O:20][c:21]2[n:22][n:23]3[cH:24][c:25]([NH:26][C:27](=[O:28])[CH:29]4[CH2:30][CH2:31]4)[n:32][c:33]3[cH:34][cH:35]2)[cH:36]1>C1CCOC1.CC(=O)N(C)C.CN(C)C=O.O=C(Cl)C(=O)Cl>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[n:6][c:7]([CH3:8])[cH:9][c:10]1[C:11](=[O:12])[NH:13][c:14]1[c:15]([F:16])[cH:17][cH:18][c:19]([O:20][c:21]2[n:22][n:23]3[cH:24][c:25]([NH:26][C:27](=[O:28])[CH:29]4[CH2:30][CH2:31]4)[n:32][c:33]3[cH:34][cH:35]2)[cH:36]1\"}",
"reactionStep": {
"id": "sa_fe136b9ed8e4577a53469b17",
"reactionHash": "001a6d7987d1e68408e5712f424ad208fc22e4cba69370c6dc38d61bb82198fd"
},
"children": [
{
"id": "9801",
"routeId": "sa_4c7ee1a737d7377a4d441795",
"moleculeId": "sa_c0057d7ba8388c056bbc4d80",
"parentId": "9800",
"isLeaf": false,
"molecule": {
"id": "sa_c0057d7ba8388c056bbc4d80",
"inchikey": "GXQNAWRYMFDOME-UHFFFAOYSA-N",
"smiles": "COCCn1nc(C)cc1C(=O)O"
},
"smiles": "COCCn1nc(C)cc1C(=O)O",
"reactionStepId": "sa_2ab4418f7e14d92408025d38",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100273788A1;0931;965283\",\"rsmi\":\"CC[O:13][C:11]([c:10]1[n:5]([CH2:4][CH2:3][O:2][CH3:1])[n:6][c:7]([CH3:8])[cH:9]1)=[O:12]>C1CCOC1.CCOC(C)=O.Cl.[Na+].O>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[n:6][c:7]([CH3:8])[cH:9][c:10]1[C:11](=[O:12])[OH:13]\"},\"mapped_reaction_smiles\":\"CC[O:13][C:11]([c:10]1[n:5]([CH2:4][CH2:3][O:2][CH3:1])[n:6][c:7]([CH3:8])[cH:9]1)=[O:12]>C1CCOC1.CCOC(C)=O.Cl.[Na+].O>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[n:6][c:7]([CH3:8])[cH:9][c:10]1[C:11](=[O:12])[OH:13]\"}",
"reactionStep": {
"id": "sa_2ab4418f7e14d92408025d38",
"reactionHash": "87395a79b774599224f9a69377a2ee1562b3cdd376abb3bcfc2a224b45b5fa3f"
},
"children": [
{
"id": "9802",
"routeId": "sa_4c7ee1a737d7377a4d441795",
"moleculeId": "sa_8890b3cdf2f78eb456d54382",
"parentId": "9801",
"isLeaf": false,
"molecule": {
"id": "sa_8890b3cdf2f78eb456d54382",
"inchikey": "MKVPBDRQSVUICR-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc(C)nn1CCOC"
},
"smiles": "CCOC(=O)c1cc(C)nn1CCOC",
"reactionStepId": "sa_03bdad8074f12e7b1a7bc846",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100273788A1;0931;965282\",\"rsmi\":\"Br[CH2:12][CH2:13][O:14][CH3:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH3:9])[n:10][nH:11]1>CN(C)C=O.[HH].[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH3:9])[n:10][n:11]1[CH2:12][CH2:13][O:14][CH3:15]\"},\"mapped_reaction_smiles\":\"Br[CH2:12][CH2:13][O:14][CH3:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH3:9])[n:10][nH:11]1>CN(C)C=O.[HH].[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH3:9])[n:10][n:11]1[CH2:12][CH2:13][O:14][CH3:15]\"}",
"reactionStep": {
"id": "sa_03bdad8074f12e7b1a7bc846",
"reactionHash": "12092e1331a3166008ab42eb80449bcae6bce03e53e7a80109cf1eebf6c21c3b"
},
"children": [
{
"id": "9803",
"routeId": "sa_4c7ee1a737d7377a4d441795",
"moleculeId": "sa_45e5cfde41d5897d8afbcef1",
"parentId": "9802",
"isLeaf": true,
"molecule": {
"id": "sa_45e5cfde41d5897d8afbcef1",
"inchikey": "BOTXQJAHRCGJEG-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc(C)[nH]n1"
},
"smiles": "CCOC(=O)c1cc(C)n[nH]1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9804",
"routeId": "sa_4c7ee1a737d7377a4d441795",
"moleculeId": "sa_1d500dd023c3a4d81d60b398",
"parentId": "9802",
"isLeaf": true,
"molecule": {
"id": "sa_1d500dd023c3a4d81d60b398",
"inchikey": "YZUPZGFPHUVJKC-UHFFFAOYSA-N",
"smiles": "COCCBr"
},
"smiles": "COCCBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "9805",
"routeId": "sa_4c7ee1a737d7377a4d441795",
"moleculeId": "sa_810db8dc28d3e4e244d27e02",
"parentId": "9800",
"isLeaf": false,
"molecule": {
"id": "sa_810db8dc28d3e4e244d27e02",
"inchikey": "HHCQVHZOJVLHIX-UHFFFAOYSA-N",
"smiles": "Nc1cc(Oc2ccc3nc(NC(=O)C4CC4)cn3n2)ccc1F"
},
"smiles": "Nc1cc(Oc2ccc3nc(NC(=O)C4CC4)cn3n2)ccc1F",
"reactionStepId": "sa_0de6ae2eddc61dec5b4c89d6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100273788A1;1310;965404\",\"rsmi\":\"I[c:9]1[n:10][n:11]2[cH:12][c:13]([NH:14][C:15](=[O:16])[CH:17]3[CH2:18][CH2:19]3)[n:20][c:21]2[cH:22][cH:23]1.[NH2:1][c:2]1[c:3]([F:4])[cH:5][cH:6][c:7]([OH:8])[cH:24]1>C1CCOC1.CCOC(C)=O.CN(C)C=O.O.O=C(O)O.Cl.[K+].[K+].[Na+]>[NH2:1][c:2]1[c:3]([F:4])[cH:5][cH:6][c:7]([O:8][c:9]2[n:10][n:11]3[cH:12][c:13]([NH:14][C:15](=[O:16])[CH:17]4[CH2:18][CH2:19]4)[n:20][c:21]3[cH:22][cH:23]2)[cH:24]1\"},\"mapped_reaction_smiles\":\"I[c:9]1[n:10][n:11]2[cH:12][c:13]([NH:14][C:15](=[O:16])[CH:17]3[CH2:18][CH2:19]3)[n:20][c:21]2[cH:22][cH:23]1.[NH2:1][c:2]1[c:3]([F:4])[cH:5][cH:6][c:7]([OH:8])[cH:24]1>C1CCOC1.CCOC(C)=O.CN(C)C=O.O.O=C(O)O.Cl.[K+].[K+].[Na+]>[NH2:1][c:2]1[c:3]([F:4])[cH:5][cH:6][c:7]([O:8][c:9]2[n:10][n:11]3[cH:12][c:13]([NH:14][C:15](=[O:16])[CH:17]4[CH2:18][CH2:19]4)[n:20][c:21]3[cH:22][cH:23]2)[cH:24]1\"}",
"reactionStep": {
"id": "sa_0de6ae2eddc61dec5b4c89d6",
"reactionHash": "55e603a4c4d768b123e0ae28573956d659e5f61b43ea4919f8c69133a3050ecc"
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"children": [
{
"id": "9806",
"routeId": "sa_4c7ee1a737d7377a4d441795",
"moleculeId": "sa_96cdde04241957ba8af0a506",
"parentId": "9805",
"isLeaf": false,
"molecule": {
"id": "sa_96cdde04241957ba8af0a506",
"inchikey": "UNNFRMZWZRJHBF-UHFFFAOYSA-N",
"smiles": "O=C(Nc1cn2nc(I)ccc2n1)C1CC1"
},
"smiles": "O=C(Nc1cn2nc(I)ccc2n1)C1CC1",
"reactionStepId": "sa_3da7bc3c7624649efb8099a2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100273788A1;0870;965258\",\"rsmi\":\"Cl[C:2](=[O:1])[CH:14]1[CH2:15][CH2:16]1.[NH2:3][c:4]1[cH:5][n:6]2[n:7][c:8]([I:9])[cH:10][cH:11][c:12]2[n:13]1>CC(=O)N(C)C.O>[O:1]=[C:2]([NH:3][c:4]1[cH:5][n:6]2[n:7][c:8]([I:9])[cH:10][cH:11][c:12]2[n:13]1)[CH:14]1[CH2:15][CH2:16]1\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[CH:14]1[CH2:15][CH2:16]1.[NH2:3][c:4]1[cH:5][n:6]2[n:7][c:8]([I:9])[cH:10][cH:11][c:12]2[n:13]1>CC(=O)N(C)C.O>[O:1]=[C:2]([NH:3][c:4]1[cH:5][n:6]2[n:7][c:8]([I:9])[cH:10][cH:11][c:12]2[n:13]1)[CH:14]1[CH2:15][CH2:16]1\"}",
"reactionStep": {
"id": "sa_3da7bc3c7624649efb8099a2",
"reactionHash": "2614114919d75ee85b99f7757a6e1e86345057ff8f8237dc4eff5c26f8bbc5d9"
},
"children": [
{
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"routeId": "sa_4c7ee1a737d7377a4d441795",
"moleculeId": "sa_d2cd98293cc7cb33db604aa3",
"parentId": "9806",
"isLeaf": false,
"molecule": {
"id": "sa_d2cd98293cc7cb33db604aa3",
"inchikey": "RXJVFGCNOQXDCR-UHFFFAOYSA-N",
"smiles": "Nc1cn2nc(I)ccc2n1"
},
"smiles": "Nc1cn2nc(I)ccc2n1",
"reactionStepId": "sa_b9e2c0fde36de79d031911f1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100273788A1;0864;965256\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:1][c:2]1[cH:3][n:4]2[n:5][c:6]([I:7])[cH:8][cH:9][c:10]2[n:11]1>CCOC(C)=O.CCOC(C)=O.CCOCC.Cl>[NH2:1][c:2]1[cH:3][n:4]2[n:5][c:6]([I:7])[cH:8][cH:9][c:10]2[n:11]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:1][c:2]1[cH:3][n:4]2[n:5][c:6]([I:7])[cH:8][cH:9][c:10]2[n:11]1>CCOC(C)=O.CCOC(C)=O.CCOCC.Cl>[NH2:1][c:2]1[cH:3][n:4]2[n:5][c:6]([I:7])[cH:8][cH:9][c:10]2[n:11]1\"}",
"reactionStep": {
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"children": [
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"moleculeId": "sa_74a39f712abc822eadbf4706",
"parentId": "9807",
"isLeaf": true,
"molecule": {
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"inchikey": "JNBWFNHTONZUNA-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)Nc1cn2nc(I)ccc2n1"
},
"smiles": "CC(C)(C)OC(=O)Nc1cn2nc(I)ccc2n1",
"reactionStepId": null,
"template": null,
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},
{
"id": "9809",
"routeId": "sa_4c7ee1a737d7377a4d441795",
"moleculeId": "sa_533af856f6df3abb2d70c000",
"parentId": "9806",
"isLeaf": true,
"molecule": {
"id": "sa_533af856f6df3abb2d70c000",
"inchikey": "ZOOSILUVXHVRJE-UHFFFAOYSA-N",
"smiles": "O=C(Cl)C1CC1"
},
"smiles": "O=C(Cl)C1CC1",
"reactionStepId": null,
"template": null,
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}
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},
{
"id": "9810",
"routeId": "sa_4c7ee1a737d7377a4d441795",
"moleculeId": "sa_76854580ec86d455961d16b3",
"parentId": "9805",
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"molecule": {
"id": "sa_76854580ec86d455961d16b3",
"inchikey": "VJCSFNNTQGRAKH-UHFFFAOYSA-N",
"smiles": "Nc1cc(O)ccc1F"
},
"smiles": "Nc1cc(O)ccc1F",
"reactionStepId": null,
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}
]
}
]
}
}