Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COCc1cc(-c2nc(-c3ccc(C(=O)N(C)CC(=O)OC)c(F)c3)no2)ccc1-c1ccccc1C
InChiKey
GPNGGUORYQVYPO-UHFFFAOYSA-N
Route Signature
f11850c1494939c40fd580309b6a113a94d91d10d81b7798ce6f70a97a61faa6
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_2faf03c1df2bc0a53fc4a509",
"signature": "f11850c1494939c40fd580309b6a113a94d91d10d81b7798ce6f70a97a61faa6",
"contentHash": "48c9bb2aaa7b11bafb1c0807d682c6edc3b77b78cbb3f6a0df4550ffa81e989b",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_268dc4bfc199e677ecdef18b",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01483",
"moleculeId": "sa_afbee9d8ba148879d61d3ec7",
"smiles": "COCc1cc(-c2nc(-c3ccc(C(=O)N(C)CC(=O)OC)c(F)c3)no2)ccc1-c1ccccc1C",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_afbee9d8ba148879d61d3ec7",
"inchikey": "GPNGGUORYQVYPO-UHFFFAOYSA-N",
"smiles": "COCc1cc(-c2nc(-c3ccc(C(=O)N(C)CC(=O)OC)c(F)c3)no2)ccc1-c1ccccc1C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14367",
"routeId": "sa_2faf03c1df2bc0a53fc4a509",
"moleculeId": "sa_afbee9d8ba148879d61d3ec7",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_afbee9d8ba148879d61d3ec7",
"inchikey": "GPNGGUORYQVYPO-UHFFFAOYSA-N",
"smiles": "COCc1cc(-c2nc(-c3ccc(C(=O)N(C)CC(=O)OC)c(F)c3)no2)ccc1-c1ccccc1C"
},
"smiles": "COCc1cc(-c2nc(-c3ccc(C(=O)N(C)CC(=O)OC)c(F)c3)no2)ccc1-c1ccccc1C",
"reactionStepId": "sa_384baf656a87df1b392360b2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08202865B2;1050;1202675\",\"rsmi\":\"Cl[C:24]([c:23]1[c:21]([F:22])[cH:20][c:19](-[c:18]2[n:17][c:16](-[c:15]3[cH:14][cH:13][c:5](-[c:6]4[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]4)[c:4]([CH2:3][O:2][CH3:1])[cH:37]3)[o:36][n:35]2)[cH:34][cH:33]1)=[O:25].[NH:26]([CH3:27])[CH2:28][C:29](=[O:30])[O:31][CH3:32]>C1CCOC1.CN(C)C=O.CN1CCOCC1.Cl.N=C=O>[CH3:1][O:2][CH2:3][c:4]1[c:5](-[c:6]2[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][c:15](-[c:16]2[n:17][c:18](-[c:19]3[cH:20][c:21]([F:22])[c:23]([C:24](=[O:25])[N:26]([CH3:27])[CH2:28][C:29](=[O:30])[O:31][CH3:32])[cH:33][cH:34]3)[n:35][o:36]2)[cH:37]1\"},\"mapped_reaction_smiles\":\"Cl[C:24]([c:23]1[c:21]([F:22])[cH:20][c:19](-[c:18]2[n:17][c:16](-[c:15]3[cH:14][cH:13][c:5](-[c:6]4[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]4)[c:4]([CH2:3][O:2][CH3:1])[cH:37]3)[o:36][n:35]2)[cH:34][cH:33]1)=[O:25].[NH:26]([CH3:27])[CH2:28][C:29](=[O:30])[O:31][CH3:32]>C1CCOC1.CN(C)C=O.CN1CCOCC1.Cl.N=C=O>[CH3:1][O:2][CH2:3][c:4]1[c:5](-[c:6]2[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][c:15](-[c:16]2[n:17][c:18](-[c:19]3[cH:20][c:21]([F:22])[c:23]([C:24](=[O:25])[N:26]([CH3:27])[CH2:28][C:29](=[O:30])[O:31][CH3:32])[cH:33][cH:34]3)[n:35][o:36]2)[cH:37]1\"}",
"reactionStep": {
"id": "sa_384baf656a87df1b392360b2",
"reactionHash": "f26499d6b3e4acf91e79d27985a126798818880cab2ce4f7bd4b4f3d7c46bb6a"
},
"children": [
{
"id": "14368",
"routeId": "sa_2faf03c1df2bc0a53fc4a509",
"moleculeId": "sa_4b34c10ebbc55ae5eff6b138",
"parentId": "14367",
"isLeaf": false,
"molecule": {
"id": "sa_4b34c10ebbc55ae5eff6b138",
"inchikey": "UAVWYOLECABNHC-UHFFFAOYSA-N",
"smiles": "COCc1cc(-c2nc(-c3ccc(C(=O)Cl)c(F)c3)no2)ccc1-c1ccccc1C"
},
"smiles": "COCc1cc(-c2nc(-c3ccc(C(=O)Cl)c(F)c3)no2)ccc1-c1ccccc1C",
"reactionStepId": "sa_4362b01f2496b64b1672ffa9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08202865B2;1050;1202674\",\"rsmi\":\"O=C(Cl)C(=O)[Cl:26].O[C:24]([c:23]1[c:21]([F:22])[cH:20][c:19](-[c:18]2[n:17][c:16](-[c:15]3[cH:14][cH:13][c:5](-[c:6]4[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]4)[c:4]([CH2:3][O:2][CH3:1])[cH:31]3)[o:30][n:29]2)[cH:28][cH:27]1)=[O:25]>CN(C)C=O.ClCCl>[CH3:1][O:2][CH2:3][c:4]1[c:5](-[c:6]2[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][c:15](-[c:16]2[n:17][c:18](-[c:19]3[cH:20][c:21]([F:22])[c:23]([C:24](=[O:25])[Cl:26])[cH:27][cH:28]3)[n:29][o:30]2)[cH:31]1\"},\"mapped_reaction_smiles\":\"O=C(Cl)C(=O)[Cl:26].O[C:24]([c:23]1[c:21]([F:22])[cH:20][c:19](-[c:18]2[n:17][c:16](-[c:15]3[cH:14][cH:13][c:5](-[c:6]4[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]4)[c:4]([CH2:3][O:2][CH3:1])[cH:31]3)[o:30][n:29]2)[cH:28][cH:27]1)=[O:25]>CN(C)C=O.ClCCl>[CH3:1][O:2][CH2:3][c:4]1[c:5](-[c:6]2[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][c:15](-[c:16]2[n:17][c:18](-[c:19]3[cH:20][c:21]([F:22])[c:23]([C:24](=[O:25])[Cl:26])[cH:27][cH:28]3)[n:29][o:30]2)[cH:31]1\"}",
"reactionStep": {
"id": "sa_4362b01f2496b64b1672ffa9",
"reactionHash": "932c470c9976df19a91a7c35b1944e4dccffae4b6a89488708c23ff041c0cfc2"
},
"children": [
{
"id": "14369",
"routeId": "sa_2faf03c1df2bc0a53fc4a509",
"moleculeId": "sa_83e7d4ec882b44062b48ca58",
"parentId": "14368",
"isLeaf": true,
"molecule": {
"id": "sa_83e7d4ec882b44062b48ca58",
"inchikey": "CTSLXHKWHWQRSH-UHFFFAOYSA-N",
"smiles": "O=C(Cl)C(=O)Cl"
},
"smiles": "O=C(Cl)C(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14370",
"routeId": "sa_2faf03c1df2bc0a53fc4a509",
"moleculeId": "sa_0b9c8cf941747a1df10e46b7",
"parentId": "14368",
"isLeaf": false,
"molecule": {
"id": "sa_0b9c8cf941747a1df10e46b7",
"inchikey": "LRLCCCHYVMATKG-UHFFFAOYSA-N",
"smiles": "COCc1cc(-c2nc(-c3ccc(C(=O)O)c(F)c3)no2)ccc1-c1ccccc1C"
},
"smiles": "COCc1cc(-c2nc(-c3ccc(C(=O)O)c(F)c3)no2)ccc1-c1ccccc1C",
"reactionStepId": "sa_7629adbfcf5dcde78d010734",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08202865B2;0833;1202629\",\"rsmi\":\"C[O:26][C:24]([c:23]1[c:21]([F:22])[cH:20][c:19](-[c:18]2[n:17][c:16](-[c:15]3[cH:14][cH:13][c:5](-[c:6]4[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]4)[c:4]([CH2:3][O:2][CH3:1])[cH:31]3)[o:30][n:29]2)[cH:28][cH:27]1)=[O:25]>C1CCOC1.CO.O.[Na+].O>[CH3:1][O:2][CH2:3][c:4]1[c:5](-[c:6]2[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][c:15](-[c:16]2[n:17][c:18](-[c:19]3[cH:20][c:21]([F:22])[c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28]3)[n:29][o:30]2)[cH:31]1\"},\"mapped_reaction_smiles\":\"C[O:26][C:24]([c:23]1[c:21]([F:22])[cH:20][c:19](-[c:18]2[n:17][c:16](-[c:15]3[cH:14][cH:13][c:5](-[c:6]4[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]4)[c:4]([CH2:3][O:2][CH3:1])[cH:31]3)[o:30][n:29]2)[cH:28][cH:27]1)=[O:25]>C1CCOC1.CO.O.[Na+].O>[CH3:1][O:2][CH2:3][c:4]1[c:5](-[c:6]2[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][c:15](-[c:16]2[n:17][c:18](-[c:19]3[cH:20][c:21]([F:22])[c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28]3)[n:29][o:30]2)[cH:31]1\"}",
"reactionStep": {
"id": "sa_7629adbfcf5dcde78d010734",
"reactionHash": "8ffd05afdd25df8ee43a13a82acaf5baf5c0f1e7db6b44ebfcd4caac28656c0f"
},
"children": [
{
"id": "14371",
"routeId": "sa_2faf03c1df2bc0a53fc4a509",
"moleculeId": "sa_e7d15b3ad531d6125a34d29d",
"parentId": "14370",
"isLeaf": false,
"molecule": {
"id": "sa_e7d15b3ad531d6125a34d29d",
"inchikey": "CRMPECJPROVYFC-UHFFFAOYSA-N",
"smiles": "COCc1cc(-c2nc(-c3ccc(C(=O)OC)c(F)c3)no2)ccc1-c1ccccc1C"
},
"smiles": "COCc1cc(-c2nc(-c3ccc(C(=O)OC)c(F)c3)no2)ccc1-c1ccccc1C",
"reactionStepId": "sa_c8d07cb680c551213d08ecb8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08202865B2;0832;1202628\",\"rsmi\":\"O=[C:16](O)[c:15]1[cH:14][cH:13][c:5](-[c:6]2[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]2)[c:4]([CH2:3][O:2][CH3:1])[cH:32]1.[NH2:17][C:18]([c:19]1[cH:20][c:21]([F:22])[c:23]([C:24](=[O:25])[O:26][CH3:27])[cH:28][cH:29]1)=[N:30][OH:31]>CN(C)C=O.Cc1ccccc1.O=C(Cl)C(=O)Cl>[CH3:1][O:2][CH2:3][c:4]1[c:5](-[c:6]2[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][c:15](-[c:16]2[n:17][c:18](-[c:19]3[cH:20][c:21]([F:22])[c:23]([C:24](=[O:25])[O:26][CH3:27])[cH:28][cH:29]3)[n:30][o:31]2)[cH:32]1\"},\"mapped_reaction_smiles\":\"O=[C:16](O)[c:15]1[cH:14][cH:13][c:5](-[c:6]2[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]2)[c:4]([CH2:3][O:2][CH3:1])[cH:32]1.[NH2:17][C:18]([c:19]1[cH:20][c:21]([F:22])[c:23]([C:24](=[O:25])[O:26][CH3:27])[cH:28][cH:29]1)=[N:30][OH:31]>CN(C)C=O.Cc1ccccc1.O=C(Cl)C(=O)Cl>[CH3:1][O:2][CH2:3][c:4]1[c:5](-[c:6]2[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][c:15](-[c:16]2[n:17][c:18](-[c:19]3[cH:20][c:21]([F:22])[c:23]([C:24](=[O:25])[O:26][CH3:27])[cH:28][cH:29]3)[n:30][o:31]2)[cH:32]1\"}",
"reactionStep": {
"id": "sa_c8d07cb680c551213d08ecb8",
"reactionHash": "4faeab0d6789b60f407016610004367ba3b5ae41f7213483d19dcb0fbef38319"
},
"children": [
{
"id": "14372",
"routeId": "sa_2faf03c1df2bc0a53fc4a509",
"moleculeId": "sa_5a059574f40da1bd750688bf",
"parentId": "14371",
"isLeaf": true,
"molecule": {
"id": "sa_5a059574f40da1bd750688bf",
"inchikey": "PIIOSGISGPCYTI-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(C(N)=NO)cc1F"
},
"smiles": "COC(=O)c1ccc(C(N)=NO)cc1F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14373",
"routeId": "sa_2faf03c1df2bc0a53fc4a509",
"moleculeId": "sa_ff94725bda5ead593d6954d5",
"parentId": "14371",
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"molecule": {
"id": "sa_ff94725bda5ead593d6954d5",
"inchikey": "YMNGMGLZWKUGGJ-UHFFFAOYSA-N",
"smiles": "COCc1cc(C(=O)O)ccc1-c1ccccc1C"
},
"smiles": "COCc1cc(C(=O)O)ccc1-c1ccccc1C",
"reactionStepId": "sa_5aaf21034c23b5dbc4da75bf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08202865B2;0557;1202519\",\"rsmi\":\"C[O:18][C:16]([c:15]1[cH:14][cH:13][c:5](-[c:6]2[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]2)[c:4]([CH2:3][O:2][CH3:1])[cH:19]1)=[O:17]>CCO.O.[Na+].O>[CH3:1][O:2][CH2:3][c:4]1[c:5](-[c:6]2[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][c:15]([C:16](=[O:17])[OH:18])[cH:19]1\"},\"mapped_reaction_smiles\":\"C[O:18][C:16]([c:15]1[cH:14][cH:13][c:5](-[c:6]2[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]2)[c:4]([CH2:3][O:2][CH3:1])[cH:19]1)=[O:17]>CCO.O.[Na+].O>[CH3:1][O:2][CH2:3][c:4]1[c:5](-[c:6]2[c:7]([CH3:8])[cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][c:15]([C:16](=[O:17])[OH:18])[cH:19]1\"}",
"reactionStep": {
"id": "sa_5aaf21034c23b5dbc4da75bf",
"reactionHash": "ca800d061d1e9c1a485d9b9252cc708123ff640a7579f32c9df448f7636478ee"
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"children": [
{
"id": "14374",
"routeId": "sa_2faf03c1df2bc0a53fc4a509",
"moleculeId": "sa_37f5ffe1be1c93cba2379f8e",
"parentId": "14373",
"isLeaf": true,
"molecule": {
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"inchikey": "BMYCXIKWTMREBD-UHFFFAOYSA-N",
"smiles": "COCc1cc(C(=O)OC)ccc1-c1ccccc1C"
},
"smiles": "COCc1cc(C(=O)OC)ccc1-c1ccccc1C",
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}
]
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]
}
]
}
]
},
{
"id": "14375",
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"moleculeId": "sa_bc57bbd9e264096723c0d430",
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"molecule": {
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"inchikey": "VXGABWCSZZWXPC-UHFFFAOYSA-N",
"smiles": "CNCC(=O)OC"
},
"smiles": "CNCC(=O)OC",
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"children": []
}
]
}
}