Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CNc1nc(Nc2cc(C)c(C(=O)N3CCOCC3)cc2Cl)ncc1C(F)(F)F
InChiKey
CGELVESSCKWNHU-UHFFFAOYSA-N
Route Signature
b09c28d63a676cd338443ab63aea6b5175af3de67584e8d17a10567d6bfb869e
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_134e9ffa743dd1fb584acb33",
"signature": "b09c28d63a676cd338443ab63aea6b5175af3de67584e8d17a10567d6bfb869e",
"contentHash": "7af96ca4ff3aba6c97ee86fdbf55c0c356ff58af6d755d1e681ced08c587ee75",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_5b77c75ddbc51e840ee18036",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-06508",
"moleculeId": "sa_300cd43c145789fa8be39b61",
"smiles": "CNc1nc(Nc2cc(C)c(C(=O)N3CCOCC3)cc2Cl)ncc1C(F)(F)F",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_300cd43c145789fa8be39b61",
"inchikey": "CGELVESSCKWNHU-UHFFFAOYSA-N",
"smiles": "CNc1nc(Nc2cc(C)c(C(=O)N3CCOCC3)cc2Cl)ncc1C(F)(F)F"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "15942",
"routeId": "sa_134e9ffa743dd1fb584acb33",
"moleculeId": "sa_300cd43c145789fa8be39b61",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_300cd43c145789fa8be39b61",
"inchikey": "CGELVESSCKWNHU-UHFFFAOYSA-N",
"smiles": "CNc1nc(Nc2cc(C)c(C(=O)N3CCOCC3)cc2Cl)ncc1C(F)(F)F"
},
"smiles": "CNc1nc(Nc2cc(C)c(C(=O)N3CCOCC3)cc2Cl)ncc1C(F)(F)F",
"reactionStepId": "sa_4de0e177987bc169d80e2776",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130157999A1;0734;1382820\",\"rsmi\":\"Cl[c:5]1[n:4][c:3]([NH:2][CH3:1])[c:25]([C:26]([F:27])([F:28])[F:29])[cH:24][n:23]1.[NH2:6][c:7]1[cH:8][c:9]([CH3:10])[c:11]([C:12](=[O:13])[N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[cH:20][c:21]1[Cl:22]>C1COCCO1.Cc1ccc(S(=O)(=O)O)cc1.ClCCl.O=C(O)O.[Na+]>[CH3:1][NH:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][c:9]([CH3:10])[c:11]([C:12](=[O:13])[N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[cH:20][c:21]2[Cl:22])[n:23][cH:24][c:25]1[C:26]([F:27])([F:28])[F:29]\"},\"mapped_reaction_smiles\":\"Cl[c:5]1[n:4][c:3]([NH:2][CH3:1])[c:25]([C:26]([F:27])([F:28])[F:29])[cH:24][n:23]1.[NH2:6][c:7]1[cH:8][c:9]([CH3:10])[c:11]([C:12](=[O:13])[N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[cH:20][c:21]1[Cl:22]>C1COCCO1.Cc1ccc(S(=O)(=O)O)cc1.ClCCl.O=C(O)O.[Na+]>[CH3:1][NH:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][c:9]([CH3:10])[c:11]([C:12](=[O:13])[N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[cH:20][c:21]2[Cl:22])[n:23][cH:24][c:25]1[C:26]([F:27])([F:28])[F:29]\"}",
"reactionStep": {
"id": "sa_4de0e177987bc169d80e2776",
"reactionHash": "3fd80240f9de8400adc6a072cd456d6729d0acbafcc7f75f08c6471269e8a09e"
},
"children": [
{
"id": "15943",
"routeId": "sa_134e9ffa743dd1fb584acb33",
"moleculeId": "sa_edb1723ac0c8a680ee85deb1",
"parentId": "15942",
"isLeaf": true,
"molecule": {
"id": "sa_edb1723ac0c8a680ee85deb1",
"inchikey": "DBZWBBJKHCGBCI-UHFFFAOYSA-N",
"smiles": "CNc1nc(Cl)ncc1C(F)(F)F"
},
"smiles": "CNc1nc(Cl)ncc1C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "15944",
"routeId": "sa_134e9ffa743dd1fb584acb33",
"moleculeId": "sa_7c866230c0d5ba7807333ae2",
"parentId": "15942",
"isLeaf": false,
"molecule": {
"id": "sa_7c866230c0d5ba7807333ae2",
"inchikey": "MPMKSPBROWGCQD-UHFFFAOYSA-N",
"smiles": "Cc1cc(N)c(Cl)cc1C(=O)N1CCOCC1"
},
"smiles": "Cc1cc(N)c(Cl)cc1C(=O)N1CCOCC1",
"reactionStepId": "sa_6b3081f4e63869ba407175eb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130157999A1;0706;1382808\",\"rsmi\":\"O=[N+:16]([O-])[c:15]1[c:13]([Cl:14])[cH:12][c:3]([C:4](=[O:5])[N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[c:2]([CH3:1])[cH:17]1>CCO.ClCCl.Cl[Sn]Cl.O.O.O.[Na+].O>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[cH:12][c:13]([Cl:14])[c:15]([NH2:16])[cH:17]1\"},\"mapped_reaction_smiles\":\"O=[N+:16]([O-])[c:15]1[c:13]([Cl:14])[cH:12][c:3]([C:4](=[O:5])[N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[c:2]([CH3:1])[cH:17]1>CCO.ClCCl.Cl[Sn]Cl.O.O.O.[Na+].O>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[cH:12][c:13]([Cl:14])[c:15]([NH2:16])[cH:17]1\"}",
"reactionStep": {
"id": "sa_6b3081f4e63869ba407175eb",
"reactionHash": "16c69a27898076818c94ae5a6339027c0aae24154e7344ee041f1b120f84f702"
},
"children": [
{
"id": "15945",
"routeId": "sa_134e9ffa743dd1fb584acb33",
"moleculeId": "sa_781c3883604bb207f8289434",
"parentId": "15944",
"isLeaf": false,
"molecule": {
"id": "sa_781c3883604bb207f8289434",
"inchikey": "HXZCHPGTYHPINM-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])c(Cl)cc1C(=O)N1CCOCC1"
},
"smiles": "Cc1cc([N+](=O)[O-])c(Cl)cc1C(=O)N1CCOCC1",
"reactionStepId": "sa_bc1a38a0d8f297a146495abc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130157999A1;0704;1382807\",\"rsmi\":\"O[C:4]([c:3]1[c:2]([CH3:1])[cH:19][c:15]([N+:16](=[O:17])[O-:18])[c:13]([Cl:14])[cH:12]1)=[O:5].[NH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1>CCN(CC)CC.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.ClCCl.F[PH](F)(F)(F)(F)F.O>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[cH:12][c:13]([Cl:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1\"},\"mapped_reaction_smiles\":\"O[C:4]([c:3]1[c:2]([CH3:1])[cH:19][c:15]([N+:16](=[O:17])[O-:18])[c:13]([Cl:14])[cH:12]1)=[O:5].[NH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1>CCN(CC)CC.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.ClCCl.F[PH](F)(F)(F)(F)F.O>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[cH:12][c:13]([Cl:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1\"}",
"reactionStep": {
"id": "sa_bc1a38a0d8f297a146495abc",
"reactionHash": "4101ecbb0f8122d3d0a346e321101b002a2d8ada8726a80cbde17a7f40301280"
},
"children": [
{
"id": "15946",
"routeId": "sa_134e9ffa743dd1fb584acb33",
"moleculeId": "sa_9d761ea9b8b3de3cf80e3ed1",
"parentId": "15945",
"isLeaf": false,
"molecule": {
"id": "sa_9d761ea9b8b3de3cf80e3ed1",
"inchikey": "DBONDNSCEDDWDL-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])c(Cl)cc1C(=O)O"
},
"smiles": "Cc1cc([N+](=O)[O-])c(Cl)cc1C(=O)O",
"reactionStepId": "sa_778c3357312efe2fa1f8573e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130157999A1;0702;1382806\",\"rsmi\":\"CC(O)=[O:5].N#[C:4][c:3]1[c:2]([CH3:1])[cH:14][c:10]([N+:11](=[O:12])[O-:13])[c:8]([Cl:9])[cH:7]1.O=S(=O)(O)[OH:6]>O>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][c:8]([Cl:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1\"},\"mapped_reaction_smiles\":\"CC(O)=[O:5].N#[C:4][c:3]1[c:2]([CH3:1])[cH:14][c:10]([N+:11](=[O:12])[O-:13])[c:8]([Cl:9])[cH:7]1.O=S(=O)(O)[OH:6]>O>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][c:8]([Cl:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1\"}",
"reactionStep": {
"id": "sa_778c3357312efe2fa1f8573e",
"reactionHash": "4483f21780ee50ab5fbe42b123cf136e34b71fe000ea3639423d241cb8067503"
},
"children": [
{
"id": "15947",
"routeId": "sa_134e9ffa743dd1fb584acb33",
"moleculeId": "sa_31ab2a9123ed4e92376ee2ec",
"parentId": "15946",
"isLeaf": false,
"molecule": {
"id": "sa_31ab2a9123ed4e92376ee2ec",
"inchikey": "ICPPDFBNUAGZKN-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])c(Cl)cc1C#N"
},
"smiles": "Cc1cc([N+](=O)[O-])c(Cl)cc1C#N",
"reactionStepId": "sa_59bddf6947b0cfbe418599c0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130157999A1;0700;1382805\",\"rsmi\":\"N#C[Cu][C:4]#[N:5].N[c:3]1[c:2]([CH3:1])[cH:13][c:9]([N+:10](=[O:11])[O-:12])[c:7]([Cl:8])[cH:6]1>CC(C)=O.CCOC(C)=O.Cl.O.O=NO.C#N.[Na+].[Na+]>[CH3:1][c:2]1[c:3]([C:4]#[N:5])[cH:6][c:7]([Cl:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13]1\"},\"mapped_reaction_smiles\":\"N#C[Cu][C:4]#[N:5].N[c:3]1[c:2]([CH3:1])[cH:13][c:9]([N+:10](=[O:11])[O-:12])[c:7]([Cl:8])[cH:6]1>CC(C)=O.CCOC(C)=O.Cl.O.O=NO.C#N.[Na+].[Na+]>[CH3:1][c:2]1[c:3]([C:4]#[N:5])[cH:6][c:7]([Cl:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13]1\"}",
"reactionStep": {
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"reactionHash": "6bf1337e8ddb9c21f87b673178bfd7678c301442e672c28e5ddcdf6fc2a89115"
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"children": [
{
"id": "15948",
"routeId": "sa_134e9ffa743dd1fb584acb33",
"moleculeId": "sa_0496e876d43435d0a0ce9c04",
"parentId": "15947",
"isLeaf": true,
"molecule": {
"id": "sa_0496e876d43435d0a0ce9c04",
"inchikey": "OJDHPAQEFDMEMC-UHFFFAOYSA-N",
"smiles": "N#[C][Cu][C]#N"
},
"smiles": "N#[C][Cu][C]#N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "15949",
"routeId": "sa_134e9ffa743dd1fb584acb33",
"moleculeId": "sa_c92f5efa2a18fb05a27b079d",
"parentId": "15947",
"isLeaf": true,
"molecule": {
"id": "sa_c92f5efa2a18fb05a27b079d",
"inchikey": "OKOSGBYZOWWAPH-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])c(Cl)cc1N"
},
"smiles": "Cc1cc([N+](=O)[O-])c(Cl)cc1N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "15950",
"routeId": "sa_134e9ffa743dd1fb584acb33",
"moleculeId": "sa_a538ca410f1833f7a9788be8",
"parentId": "15946",
"isLeaf": true,
"molecule": {
"id": "sa_a538ca410f1833f7a9788be8",
"inchikey": "QAOWNCQODCNURD-UHFFFAOYSA-N",
"smiles": "O=S(=O)(O)O"
},
"smiles": "O=S(=O)(O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "15951",
"routeId": "sa_134e9ffa743dd1fb584acb33",
"moleculeId": "sa_f1a25cbb2070f020dbe1fb4a",
"parentId": "15946",
"isLeaf": true,
"molecule": {
"id": "sa_f1a25cbb2070f020dbe1fb4a",
"inchikey": "QTBSBXVTEAMEQO-UHFFFAOYSA-N",
"smiles": "CC(=O)O"
},
"smiles": "CC(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "15952",
"routeId": "sa_134e9ffa743dd1fb584acb33",
"moleculeId": "sa_39d71c291f7fdf13918cc969",
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"molecule": {
"id": "sa_39d71c291f7fdf13918cc969",
"inchikey": "YNAVUWVOSKDBBP-UHFFFAOYSA-N",
"smiles": "C1COCCN1"
},
"smiles": "C1COCCN1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
}