Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Nc1cc(C(F)(F)F)cc(C(=O)Nc2ccc(Cl)c(Cl)c2)c1N1CCCCC1
InChiKey
BJNDUCJJYVJHQL-UHFFFAOYSA-N
Route Signature
d8d391bde29e9be96a5967d6d02a14ec2b05bcb371ec85fef2d9184177e1080c
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_6d9a246be90075daebf55f9a",
"signature": "d8d391bde29e9be96a5967d6d02a14ec2b05bcb371ec85fef2d9184177e1080c",
"contentHash": "8ad731280b2940f104d9577eae69b54ce095c11905c356fc80297d5ba67256bc",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_4e4fbbf4de76ce4833e60274",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01170",
"moleculeId": "sa_335e70dec180959d45e588b7",
"smiles": "Nc1cc(C(F)(F)F)cc(C(=O)Nc2ccc(Cl)c(Cl)c2)c1N1CCCCC1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_335e70dec180959d45e588b7",
"inchikey": "BJNDUCJJYVJHQL-UHFFFAOYSA-N",
"smiles": "Nc1cc(C(F)(F)F)cc(C(=O)Nc2ccc(Cl)c(Cl)c2)c1N1CCCCC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14122",
"routeId": "sa_6d9a246be90075daebf55f9a",
"moleculeId": "sa_335e70dec180959d45e588b7",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_335e70dec180959d45e588b7",
"inchikey": "BJNDUCJJYVJHQL-UHFFFAOYSA-N",
"smiles": "Nc1cc(C(F)(F)F)cc(C(=O)Nc2ccc(Cl)c(Cl)c2)c1N1CCCCC1"
},
"smiles": "Nc1cc(C(F)(F)F)cc(C(=O)Nc2ccc(Cl)c(Cl)c2)c1N1CCCCC1",
"reactionStepId": "sa_8a346bd2b4d80f1158e6c3c6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080119459A1;0127;573111\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][c:10]([C:11](=[O:12])[NH:13][c:14]2[cH:15][c:16]([Cl:17])[c:18]([Cl:19])[cH:20][cH:21]2)[c:22]1[N:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1>C1CCOC1.[H][H].[Ni]>[NH2:1][c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][c:10]([C:11](=[O:12])[NH:13][c:14]2[cH:15][c:16]([Cl:17])[c:18]([Cl:19])[cH:20][cH:21]2)[c:22]1[N:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][c:10]([C:11](=[O:12])[NH:13][c:14]2[cH:15][c:16]([Cl:17])[c:18]([Cl:19])[cH:20][cH:21]2)[c:22]1[N:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1>C1CCOC1.[H][H].[Ni]>[NH2:1][c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][c:10]([C:11](=[O:12])[NH:13][c:14]2[cH:15][c:16]([Cl:17])[c:18]([Cl:19])[cH:20][cH:21]2)[c:22]1[N:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1\"}",
"reactionStep": {
"id": "sa_8a346bd2b4d80f1158e6c3c6",
"reactionHash": "143c0b32973ada4393539e86673d0933d26468d0ad094b2c5ae436db7ebda5d5"
},
"children": [
{
"id": "14123",
"routeId": "sa_6d9a246be90075daebf55f9a",
"moleculeId": "sa_022d12edd15a1f30bdca0ba3",
"parentId": "14122",
"isLeaf": false,
"molecule": {
"id": "sa_022d12edd15a1f30bdca0ba3",
"inchikey": "BKTPEXJEXYMMIZ-UHFFFAOYSA-N",
"smiles": "O=C(Nc1ccc(Cl)c(Cl)c1)c1cc(C(F)(F)F)cc([N+](=O)[O-])c1N1CCCCC1"
},
"smiles": "O=C(Nc1ccc(Cl)c(Cl)c1)c1cc(C(F)(F)F)cc([N+](=O)[O-])c1N1CCCCC1",
"reactionStepId": "sa_d053c3036e9250ad7f122ead",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080119459A1;0125;573110\",\"rsmi\":\"Cl[c:13]1[c:12]([C:2](=[O:1])[NH:3][c:4]2[cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10][cH:11]2)[cH:30][c:25]([C:26]([F:27])([F:28])[F:29])[cH:24][c:20]1[N+:21](=[O:22])[O-:23].[NH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>C1COCCO1.CCCCCC.CCOCC.O>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10][cH:11]1)[c:12]1[c:13]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[c:20]([N+:21](=[O:22])[O-:23])[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]1\"},\"mapped_reaction_smiles\":\"Cl[c:13]1[c:12]([C:2](=[O:1])[NH:3][c:4]2[cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10][cH:11]2)[cH:30][c:25]([C:26]([F:27])([F:28])[F:29])[cH:24][c:20]1[N+:21](=[O:22])[O-:23].[NH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>C1COCCO1.CCCCCC.CCOCC.O>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10][cH:11]1)[c:12]1[c:13]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[c:20]([N+:21](=[O:22])[O-:23])[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]1\"}",
"reactionStep": {
"id": "sa_d053c3036e9250ad7f122ead",
"reactionHash": "a319aeeb2166d6427b96a72191466ad4f1aa5ca076d57c57b65aae3a9ed9c7af"
},
"children": [
{
"id": "14124",
"routeId": "sa_6d9a246be90075daebf55f9a",
"moleculeId": "sa_c8165ca744c1ef2625930884",
"parentId": "14123",
"isLeaf": false,
"molecule": {
"id": "sa_c8165ca744c1ef2625930884",
"inchikey": "LDSXDYKWXUEVAJ-UHFFFAOYSA-N",
"smiles": "O=C(Nc1ccc(Cl)c(Cl)c1)c1cc(C(F)(F)F)cc([N+](=O)[O-])c1Cl"
},
"smiles": "O=C(Nc1ccc(Cl)c(Cl)c1)c1cc(C(F)(F)F)cc([N+](=O)[O-])c1Cl",
"reactionStepId": "sa_965f480c1fcf0896553994fe",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080119459A1;0123;573109\",\"rsmi\":\"Cl[C:2](=[O:1])[c:12]1[c:13]([Cl:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25]1.[NH2:3][c:4]1[cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10][cH:11]1>CC(C)=O.CC(C)=O.O.O>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10][cH:11]1)[c:12]1[c:13]([Cl:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25]1\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[c:12]1[c:13]([Cl:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25]1.[NH2:3][c:4]1[cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10][cH:11]1>CC(C)=O.CC(C)=O.O.O>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10][cH:11]1)[c:12]1[c:13]([Cl:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25]1\"}",
"reactionStep": {
"id": "sa_965f480c1fcf0896553994fe",
"reactionHash": "32d9adaffb3dc3bd3673d68eb615fd5a354c0eb467a69afd13e2d8a8b02da0b3"
},
"children": [
{
"id": "14125",
"routeId": "sa_6d9a246be90075daebf55f9a",
"moleculeId": "sa_43238655fa6f820faaad70ee",
"parentId": "14124",
"isLeaf": false,
"molecule": {
"id": "sa_43238655fa6f820faaad70ee",
"inchikey": "MOWGCWIDCJFGFG-UHFFFAOYSA-N",
"smiles": "O=C(Cl)c1cc(C(F)(F)F)cc([N+](=O)[O-])c1Cl"
},
"smiles": "O=C(Cl)c1cc(C(F)(F)F)cc([N+](=O)[O-])c1Cl",
"reactionStepId": "sa_c5f1d53163a35f2dc985272a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080119459A1;0122;573108\",\"rsmi\":\"O=S(Cl)[Cl:3].O[C:2](=[O:1])[c:4]1[c:5]([Cl:6])[c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1>Cc1ccccc1>[O:1]=[C:2]([Cl:3])[c:4]1[c:5]([Cl:6])[c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1\"},\"mapped_reaction_smiles\":\"O=S(Cl)[Cl:3].O[C:2](=[O:1])[c:4]1[c:5]([Cl:6])[c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1>Cc1ccccc1>[O:1]=[C:2]([Cl:3])[c:4]1[c:5]([Cl:6])[c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1\"}",
"reactionStep": {
"id": "sa_c5f1d53163a35f2dc985272a",
"reactionHash": "51657f68a43c0ac8a7aa0b9628a50e29c936fa655fbf6d24681cfc941efa108a"
},
"children": [
{
"id": "14126",
"routeId": "sa_6d9a246be90075daebf55f9a",
"moleculeId": "sa_cd67ce42f230ef1a4063353c",
"parentId": "14125",
"isLeaf": true,
"molecule": {
"id": "sa_cd67ce42f230ef1a4063353c",
"inchikey": "FYSNRJHAOHDILO-UHFFFAOYSA-N",
"smiles": "O=S(Cl)Cl"
},
"smiles": "O=S(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14127",
"routeId": "sa_6d9a246be90075daebf55f9a",
"moleculeId": "sa_273df9166099044792e34569",
"parentId": "14125",
"isLeaf": false,
"molecule": {
"id": "sa_273df9166099044792e34569",
"inchikey": "PSRPKTROFCUEOD-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cc(C(F)(F)F)cc([N+](=O)[O-])c1Cl"
},
"smiles": "O=C(O)c1cc(C(F)(F)F)cc([N+](=O)[O-])c1Cl",
"reactionStepId": "sa_0e69aaa882313e5d83b11ce4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080119459A1;0120;573107\",\"rsmi\":\"O[N+:8](=[O:9])[O-:10].[O:1]=[C:2]([OH:3])[c:4]1[c:5]([Cl:6])[cH:7][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1>O=S(=O)(O)O>[O:1]=[C:2]([OH:3])[c:4]1[c:5]([Cl:6])[c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1\"},\"mapped_reaction_smiles\":\"O[N+:8](=[O:9])[O-:10].[O:1]=[C:2]([OH:3])[c:4]1[c:5]([Cl:6])[cH:7][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1>O=S(=O)(O)O>[O:1]=[C:2]([OH:3])[c:4]1[c:5]([Cl:6])[c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1\"}",
"reactionStep": {
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"reactionHash": "28f0eb5cb64eb4572acf69e6d0446935f30661dc084eb96791d05efdecb5fef6"
},
"children": [
{
"id": "14128",
"routeId": "sa_6d9a246be90075daebf55f9a",
"moleculeId": "sa_edac0a7fd043198784a28dd9",
"parentId": "14127",
"isLeaf": true,
"molecule": {
"id": "sa_edac0a7fd043198784a28dd9",
"inchikey": "GRYLNZFGIOXLOG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])O"
},
"smiles": "O=[N+]([O-])O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14129",
"routeId": "sa_6d9a246be90075daebf55f9a",
"moleculeId": "sa_3469637d47a8f13e241ff80b",
"parentId": "14127",
"isLeaf": true,
"molecule": {
"id": "sa_3469637d47a8f13e241ff80b",
"inchikey": "WLXRKCGYQAKHSJ-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cc(C(F)(F)F)ccc1Cl"
},
"smiles": "O=C(O)c1cc(C(F)(F)F)ccc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
},
{
"id": "14130",
"routeId": "sa_6d9a246be90075daebf55f9a",
"moleculeId": "sa_be039d4b6b52d2029512e7b4",
"parentId": "14124",
"isLeaf": true,
"molecule": {
"id": "sa_be039d4b6b52d2029512e7b4",
"inchikey": "SDYWXFYBZPNOFX-UHFFFAOYSA-N",
"smiles": "Nc1ccc(Cl)c(Cl)c1"
},
"smiles": "Nc1ccc(Cl)c(Cl)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
},
{
"id": "14131",
"routeId": "sa_6d9a246be90075daebf55f9a",
"moleculeId": "sa_60b03dbd902de8f42159b182",
"parentId": "14123",
"isLeaf": true,
"molecule": {
"id": "sa_60b03dbd902de8f42159b182",
"inchikey": "NQRYJNQNLNOLGT-UHFFFAOYSA-N",
"smiles": "C1CCNCC1"
},
"smiles": "C1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}