Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCc1nc2c(Cl)ccc(OCC(=O)O)c2c(OC(F)F)c1Cc1ccc(C(=O)C(C)C)cc1
InChiKey
MOVBPHAJFDHDSZ-UHFFFAOYSA-N
Route Signature
ca9aa24d40445db39948c98ca1d076f9f5438b75fb51500d3efd1afef04f64a4
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_e1a194d7891ba98248d0db53",
"signature": "ca9aa24d40445db39948c98ca1d076f9f5438b75fb51500d3efd1afef04f64a4",
"contentHash": "e131c46090829e0445ca2c5d09ae90c4101c414d691d2bbf4f6abc82bd842384",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_91ecf611a26f0f39d76b6ef5",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00329",
"moleculeId": "sa_f0704b673653c45899becdbd",
"smiles": "CCc1nc2c(Cl)ccc(OCC(=O)O)c2c(OC(F)F)c1Cc1ccc(C(=O)C(C)C)cc1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_f0704b673653c45899becdbd",
"inchikey": "MOVBPHAJFDHDSZ-UHFFFAOYSA-N",
"smiles": "CCc1nc2c(Cl)ccc(OCC(=O)O)c2c(OC(F)F)c1Cc1ccc(C(=O)C(C)C)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9405",
"routeId": "sa_e1a194d7891ba98248d0db53",
"moleculeId": "sa_f0704b673653c45899becdbd",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f0704b673653c45899becdbd",
"inchikey": "MOVBPHAJFDHDSZ-UHFFFAOYSA-N",
"smiles": "CCc1nc2c(Cl)ccc(OCC(=O)O)c2c(OC(F)F)c1Cc1ccc(C(=O)C(C)C)cc1"
},
"smiles": "CCc1nc2c(Cl)ccc(OCC(=O)O)c2c(OC(F)F)c1Cc1ccc(C(=O)C(C)C)cc1",
"reactionStepId": "sa_cf175552c0c9d507df01dcb4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08173812B2;0220;1187606\",\"rsmi\":\"C[O:15][C:13]([CH2:12][O:11][c:10]1[cH:9][cH:8][c:6]([Cl:7])[c:5]2[n:4][c:3]([CH2:2][CH3:1])[c:22]([CH2:23][c:24]3[cH:25][cH:26][c:27]([C:28](=[O:29])[CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]3)[c:17]([O:18][CH:19]([F:20])[F:21])[c:16]21)=[O:14]>C1CCOC1.O.[Li+].O>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([Cl:7])[cH:8][cH:9][c:10]([O:11][CH2:12][C:13](=[O:14])[OH:15])[c:16]2[c:17]([O:18][CH:19]([F:20])[F:21])[c:22]1[CH2:23][c:24]1[cH:25][cH:26][c:27]([C:28](=[O:29])[CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]1\"},\"mapped_reaction_smiles\":\"C[O:15][C:13]([CH2:12][O:11][c:10]1[cH:9][cH:8][c:6]([Cl:7])[c:5]2[n:4][c:3]([CH2:2][CH3:1])[c:22]([CH2:23][c:24]3[cH:25][cH:26][c:27]([C:28](=[O:29])[CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]3)[c:17]([O:18][CH:19]([F:20])[F:21])[c:16]21)=[O:14]>C1CCOC1.O.[Li+].O>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([Cl:7])[cH:8][cH:9][c:10]([O:11][CH2:12][C:13](=[O:14])[OH:15])[c:16]2[c:17]([O:18][CH:19]([F:20])[F:21])[c:22]1[CH2:23][c:24]1[cH:25][cH:26][c:27]([C:28](=[O:29])[CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]1\"}",
"reactionStep": {
"id": "sa_cf175552c0c9d507df01dcb4",
"reactionHash": "deb47cf05de690d494866cd80e4a8b0aad339096600625cc1ddfb8798c719533"
},
"children": [
{
"id": "9406",
"routeId": "sa_e1a194d7891ba98248d0db53",
"moleculeId": "sa_66a2c9347e0fce512531ee6c",
"parentId": "9405",
"isLeaf": false,
"molecule": {
"id": "sa_66a2c9347e0fce512531ee6c",
"inchikey": "BHFTYALYXUOYML-UHFFFAOYSA-N",
"smiles": "CCc1nc2c(Cl)ccc(OCC(=O)OC)c2c(OC(F)F)c1Cc1ccc(C(=O)C(C)C)cc1"
},
"smiles": "CCc1nc2c(Cl)ccc(OCC(=O)OC)c2c(OC(F)F)c1Cc1ccc(C(=O)C(C)C)cc1",
"reactionStepId": "sa_cf323afb3f8b94daad64f2d0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08173812B2;0218;1187605\",\"rsmi\":\"Cl[CH:20]([F:21])[F:22].[CH3:1][CH2:2][c:3]1[nH:4][c:5]2[c:6]([Cl:7])[cH:8][cH:9][c:10]([O:11][CH2:12][C:13](=[O:14])[O:15][CH3:16])[c:17]2[c:18](=[O:19])[c:23]1[CH2:24][c:25]1[cH:26][cH:27][c:28]([C:29](=[O:30])[CH:31]([CH3:32])[CH3:33])[cH:34][cH:35]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([Cl:7])[cH:8][cH:9][c:10]([O:11][CH2:12][C:13](=[O:14])[O:15][CH3:16])[c:17]2[c:18]([O:19][CH:20]([F:21])[F:22])[c:23]1[CH2:24][c:25]1[cH:26][cH:27][c:28]([C:29](=[O:30])[CH:31]([CH3:32])[CH3:33])[cH:34][cH:35]1\"},\"mapped_reaction_smiles\":\"Cl[CH:20]([F:21])[F:22].[CH3:1][CH2:2][c:3]1[nH:4][c:5]2[c:6]([Cl:7])[cH:8][cH:9][c:10]([O:11][CH2:12][C:13](=[O:14])[O:15][CH3:16])[c:17]2[c:18](=[O:19])[c:23]1[CH2:24][c:25]1[cH:26][cH:27][c:28]([C:29](=[O:30])[CH:31]([CH3:32])[CH3:33])[cH:34][cH:35]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([Cl:7])[cH:8][cH:9][c:10]([O:11][CH2:12][C:13](=[O:14])[O:15][CH3:16])[c:17]2[c:18]([O:19][CH:20]([F:21])[F:22])[c:23]1[CH2:24][c:25]1[cH:26][cH:27][c:28]([C:29](=[O:30])[CH:31]([CH3:32])[CH3:33])[cH:34][cH:35]1\"}",
"reactionStep": {
"id": "sa_cf323afb3f8b94daad64f2d0",
"reactionHash": "7bbdb7822ae8b7a96fa1190763d2fb9ac738035d2453ae1c8a2f0c46cd784dc8"
},
"children": [
{
"id": "9407",
"routeId": "sa_e1a194d7891ba98248d0db53",
"moleculeId": "sa_5947b347e5928cc878f2c73f",
"parentId": "9406",
"isLeaf": false,
"molecule": {
"id": "sa_5947b347e5928cc878f2c73f",
"inchikey": "BUMYUNUHMZBVBO-UHFFFAOYSA-N",
"smiles": "CCc1[nH]c2c(Cl)ccc(OCC(=O)OC)c2c(=O)c1Cc1ccc(C(=O)C(C)C)cc1"
},
"smiles": "CCc1[nH]c2c(Cl)ccc(OCC(=O)OC)c2c(=O)c1Cc1ccc(C(=O)C(C)C)cc1",
"reactionStepId": "sa_7e757720ae2bd58f5b817aaf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08173812B2;0216;1187604\",\"rsmi\":\"CCO[C:17]([CH:4]([C:3](=O)[CH2:2][CH3:1])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]1)=[O:18].[cH:19]1[c:20]([O:21][CH2:22][C:23](=[O:24])[O:25][CH3:26])[cH:27][cH:28][c:29]([Cl:30])[c:31]1[NH2:32]>>[CH3:1][CH2:2][c:3]1[c:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([C:10](=[O:11])[CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]2)[c:17](=[O:18])[c:19]2[c:20]([O:21][CH2:22][C:23](=[O:24])[O:25][CH3:26])[cH:27][cH:28][c:29]([Cl:30])[c:31]2[nH:32]1\"},\"mapped_reaction_smiles\":\"CCO[C:17]([CH:4]([C:3](=O)[CH2:2][CH3:1])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]1)=[O:18].[cH:19]1[c:20]([O:21][CH2:22][C:23](=[O:24])[O:25][CH3:26])[cH:27][cH:28][c:29]([Cl:30])[c:31]1[NH2:32]>>[CH3:1][CH2:2][c:3]1[c:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([C:10](=[O:11])[CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]2)[c:17](=[O:18])[c:19]2[c:20]([O:21][CH2:22][C:23](=[O:24])[O:25][CH3:26])[cH:27][cH:28][c:29]([Cl:30])[c:31]2[nH:32]1\"}",
"reactionStep": {
"id": "sa_7e757720ae2bd58f5b817aaf",
"reactionHash": "2d86028fbdec3041df3486fc6d363924013a6f904b4ba0529620bf74fa6aafa0"
},
"children": [
{
"id": "9408",
"routeId": "sa_e1a194d7891ba98248d0db53",
"moleculeId": "sa_d9ad57e7f64eacc8bb0c8e5d",
"parentId": "9407",
"isLeaf": false,
"molecule": {
"id": "sa_d9ad57e7f64eacc8bb0c8e5d",
"inchikey": "BNWMBAKERONWEE-UHFFFAOYSA-N",
"smiles": "COC(=O)COc1ccc(Cl)c(N)c1"
},
"smiles": "COC(=O)COc1ccc(Cl)c(N)c1",
"reactionStepId": "sa_b7276791599b39153e4260b1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08173812B2;0145;1187582\",\"rsmi\":\"O=[N+:10]([O-])[c:9]1[cH:8][c:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:14][cH:13][c:11]1[Cl:12]>CO.O.Cl.[Fe].N.[Na+].O>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([NH2:10])[c:11]([Cl:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"O=[N+:10]([O-])[c:9]1[cH:8][c:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:14][cH:13][c:11]1[Cl:12]>CO.O.Cl.[Fe].N.[Na+].O>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([NH2:10])[c:11]([Cl:12])[cH:13][cH:14]1\"}",
"reactionStep": {
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"reactionHash": "21409a7c6cef548abe27b4214e2a9907761a3eebb8acb7e01b0cf749e4ad7bce"
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"children": [
{
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"moleculeId": "sa_022074a8deca0fde2376db37",
"parentId": "9408",
"isLeaf": false,
"molecule": {
"id": "sa_022074a8deca0fde2376db37",
"inchikey": "QCJDEMISHMKHEW-UHFFFAOYSA-N",
"smiles": "COC(=O)COc1ccc(Cl)c([N+](=O)[O-])c1"
},
"smiles": "COC(=O)COc1ccc(Cl)c([N+](=O)[O-])c1",
"reactionStepId": "sa_3415b672fd75edd641053d1c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08173812B2;0143;1187581\",\"rsmi\":\"Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]([Cl:14])[cH:15][cH:16]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]([Cl:14])[cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]([Cl:14])[cH:15][cH:16]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]([Cl:14])[cH:15][cH:16]1\"}",
"reactionStep": {
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"reactionHash": "ee8bc8709c6c13f34b90572dfc25ebb48d2f81d3d45ff18b512877c68a487b09"
},
"children": [
{
"id": "9410",
"routeId": "sa_e1a194d7891ba98248d0db53",
"moleculeId": "sa_cd5dda584af87e4e664171eb",
"parentId": "9409",
"isLeaf": true,
"molecule": {
"id": "sa_cd5dda584af87e4e664171eb",
"inchikey": "JUIKCULGDIZNDI-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(O)ccc1Cl"
},
"smiles": "O=[N+]([O-])c1cc(O)ccc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "9411",
"routeId": "sa_e1a194d7891ba98248d0db53",
"moleculeId": "sa_d6971278542e932ae568b29f",
"parentId": "9409",
"isLeaf": true,
"molecule": {
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"inchikey": "YDCHPLOFQATIDS-UHFFFAOYSA-N",
"smiles": "COC(=O)CBr"
},
"smiles": "COC(=O)CBr",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
},
{
"id": "9412",
"routeId": "sa_e1a194d7891ba98248d0db53",
"moleculeId": "sa_7a9113116f90c465d4f95676",
"parentId": "9407",
"isLeaf": false,
"molecule": {
"id": "sa_7a9113116f90c465d4f95676",
"inchikey": "NNVIVCUEGPKROE-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(Cc1ccc(C(=O)C(C)C)cc1)C(=O)CC"
},
"smiles": "CCOC(=O)C(Cc1ccc(C(=O)C(C)C)cc1)C(=O)CC",
"reactionStepId": "sa_5f017da783da76a4d79edf83",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08173812B2;0214;1187603\",\"rsmi\":\"Br[CH2:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:19](=[O:20])[CH2:21][CH3:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]1)[C:19](=[O:20])[CH2:21][CH3:22]\"},\"mapped_reaction_smiles\":\"Br[CH2:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:19](=[O:20])[CH2:21][CH3:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]1)[C:19](=[O:20])[CH2:21][CH3:22]\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"inchikey": "DGHDHWFHJPGAGC-UHFFFAOYSA-N",
"smiles": "CC(C)C(=O)c1ccc(CBr)cc1"
},
"smiles": "CC(C)C(=O)c1ccc(CBr)cc1",
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},
{
"id": "9414",
"routeId": "sa_e1a194d7891ba98248d0db53",
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"molecule": {
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"inchikey": "UDRCONFHWYGWFI-UHFFFAOYSA-N",
"smiles": "CCOC(=O)CC(=O)CC"
},
"smiles": "CCOC(=O)CC(=O)CC",
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}
]
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]
},
{
"id": "9415",
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"moleculeId": "sa_9fb3693dd82f8754813d4318",
"parentId": "9406",
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"molecule": {
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"inchikey": "VOPWNXZWBYDODV-UHFFFAOYSA-N",
"smiles": "FC(F)Cl"
},
"smiles": "FC(F)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
}