Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCn1cc(N2CCN(C(=O)OC)CC2=O)c2ccc(OCc3ccccn3)nc21
InChiKey
USINPURSDVXTPP-UHFFFAOYSA-N
Route Signature
62272aaa5e6e85cc0cba3d2f942b9b0a8079f40d2d0b542e0cbeb03e4af39676
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_265b0924917971a6cbf42183",
"signature": "62272aaa5e6e85cc0cba3d2f942b9b0a8079f40d2d0b542e0cbeb03e4af39676",
"contentHash": "9dd76d0745ffa55e4474cb41da864bc278ad61ca51f860f4386e06bf021bf654",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_f3900394b6d9edd3edbedef2",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00792",
"moleculeId": "sa_45dcc4261abdd8481575b574",
"smiles": "CCn1cc(N2CCN(C(=O)OC)CC2=O)c2ccc(OCc3ccccn3)nc21",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_45dcc4261abdd8481575b574",
"inchikey": "USINPURSDVXTPP-UHFFFAOYSA-N",
"smiles": "CCn1cc(N2CCN(C(=O)OC)CC2=O)c2ccc(OCc3ccccn3)nc21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "4896",
"routeId": "sa_265b0924917971a6cbf42183",
"moleculeId": "sa_45dcc4261abdd8481575b574",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_45dcc4261abdd8481575b574",
"inchikey": "USINPURSDVXTPP-UHFFFAOYSA-N",
"smiles": "CCn1cc(N2CCN(C(=O)OC)CC2=O)c2ccc(OCc3ccccn3)nc21"
},
"smiles": "CCn1cc(N2CCN(C(=O)OC)CC2=O)c2ccc(OCc3ccccn3)nc21",
"reactionStepId": "sa_df6de46f1ac2098f4f07432e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225602A1;0133;1414825\",\"rsmi\":\"Cl[C:10](=[O:11])[O:12][CH3:13].[CH3:1][CH2:2][n:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:14][C:15]2=[O:16])[c:17]2[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]3[n:24][cH:25][cH:26][cH:27][cH:28]3)[n:29][c:30]12>CCN(CC)CC.CO.ClCCl>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][CH3:13])[CH2:14][C:15]2=[O:16])[c:17]2[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]3[n:24][cH:25][cH:26][cH:27][cH:28]3)[n:29][c:30]12\"},\"mapped_reaction_smiles\":\"Cl[C:10](=[O:11])[O:12][CH3:13].[CH3:1][CH2:2][n:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:14][C:15]2=[O:16])[c:17]2[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]3[n:24][cH:25][cH:26][cH:27][cH:28]3)[n:29][c:30]12>CCN(CC)CC.CO.ClCCl>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][CH3:13])[CH2:14][C:15]2=[O:16])[c:17]2[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]3[n:24][cH:25][cH:26][cH:27][cH:28]3)[n:29][c:30]12\"}",
"reactionStep": {
"id": "sa_df6de46f1ac2098f4f07432e",
"reactionHash": "1a577e317c2380096ed5cf7391bd5d75c1cd2a4275048b8e79a13e1ded93b9c5"
},
"children": [
{
"id": "4897",
"routeId": "sa_265b0924917971a6cbf42183",
"moleculeId": "sa_b00cb898b7286bada6a311f6",
"parentId": "4896",
"isLeaf": false,
"molecule": {
"id": "sa_b00cb898b7286bada6a311f6",
"inchikey": "ILRDOXLJTQUVQT-UHFFFAOYSA-N",
"smiles": "CCn1cc(N2CCNCC2=O)c2ccc(OCc3ccccn3)nc21"
},
"smiles": "CCn1cc(N2CCNCC2=O)c2ccc(OCc3ccccn3)nc21",
"reactionStepId": "sa_78f85af728164f1f8384e25e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225602A1;0110;1414814\",\"rsmi\":\"CC(C)(C)OC(=O)[N:9]1[CH2:8][CH2:7][N:6]([c:5]2[cH:4][n:3]([CH2:2][CH3:1])[c:26]3[c:13]2[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]2[n:20][cH:21][cH:22][cH:23][cH:24]2)[n:25]3)[C:11](=[O:12])[CH2:10]1>CO.ClCCl.O=C(O)C(F)(F)F>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:11]2=[O:12])[c:13]2[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]3[n:20][cH:21][cH:22][cH:23][cH:24]3)[n:25][c:26]12\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:9]1[CH2:8][CH2:7][N:6]([c:5]2[cH:4][n:3]([CH2:2][CH3:1])[c:26]3[c:13]2[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]2[n:20][cH:21][cH:22][cH:23][cH:24]2)[n:25]3)[C:11](=[O:12])[CH2:10]1>CO.ClCCl.O=C(O)C(F)(F)F>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:11]2=[O:12])[c:13]2[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]3[n:20][cH:21][cH:22][cH:23][cH:24]3)[n:25][c:26]12\"}",
"reactionStep": {
"id": "sa_78f85af728164f1f8384e25e",
"reactionHash": "4706f1646ff8fd6abc54a146588db5888ee5bf8ab3b4cc300a2bd98e4a774522"
},
"children": [
{
"id": "4898",
"routeId": "sa_265b0924917971a6cbf42183",
"moleculeId": "sa_b7b75384e97c96500cdc47e5",
"parentId": "4897",
"isLeaf": false,
"molecule": {
"id": "sa_b7b75384e97c96500cdc47e5",
"inchikey": "UHYXGROPMCNJGF-UHFFFAOYSA-N",
"smiles": "CCn1cc(N2CCN(C(=O)OC(C)(C)C)CC2=O)c2ccc(OCc3ccccn3)nc21"
},
"smiles": "CCn1cc(N2CCN(C(=O)OC(C)(C)C)CC2=O)c2ccc(OCc3ccccn3)nc21",
"reactionStepId": "sa_10fc7c26799f01de7472bc57",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225602A1;0108;1414813\",\"rsmi\":\"F[c:23]1[cH:22][cH:21][c:20]2[c:5]([N:6]3[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]3=[O:19])[cH:4][n:3]([CH2:2][CH3:1])[c:33]2[n:32]1.[OH:24][CH2:25][c:26]1[n:27][cH:28][cH:29][cH:30][cH:31]1>CS(C)=O.[HH].[Na+]>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]2=[O:19])[c:20]2[cH:21][cH:22][c:23]([O:24][CH2:25][c:26]3[n:27][cH:28][cH:29][cH:30][cH:31]3)[n:32][c:33]12\"},\"mapped_reaction_smiles\":\"F[c:23]1[cH:22][cH:21][c:20]2[c:5]([N:6]3[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]3=[O:19])[cH:4][n:3]([CH2:2][CH3:1])[c:33]2[n:32]1.[OH:24][CH2:25][c:26]1[n:27][cH:28][cH:29][cH:30][cH:31]1>CS(C)=O.[HH].[Na+]>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]2=[O:19])[c:20]2[cH:21][cH:22][c:23]([O:24][CH2:25][c:26]3[n:27][cH:28][cH:29][cH:30][cH:31]3)[n:32][c:33]12\"}",
"reactionStep": {
"id": "sa_10fc7c26799f01de7472bc57",
"reactionHash": "e6ca2d9e8d1727634fcd418c967bba5b22aa278d57dfdf1c595d92f3b444c78f"
},
"children": [
{
"id": "4899",
"routeId": "sa_265b0924917971a6cbf42183",
"moleculeId": "sa_bba0480b3c5ea54b8289dc00",
"parentId": "4898",
"isLeaf": true,
"molecule": {
"id": "sa_bba0480b3c5ea54b8289dc00",
"inchikey": "SHNUBALDGXWUJI-UHFFFAOYSA-N",
"smiles": "OCc1ccccn1"
},
"smiles": "OCc1ccccn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4900",
"routeId": "sa_265b0924917971a6cbf42183",
"moleculeId": "sa_8ec1cc7695c299540f28881f",
"parentId": "4898",
"isLeaf": false,
"molecule": {
"id": "sa_8ec1cc7695c299540f28881f",
"inchikey": "VFOGVVGJXQEVRH-UHFFFAOYSA-N",
"smiles": "CCn1cc(N2CCN(C(=O)OC(C)(C)C)CC2=O)c2ccc(F)nc21"
},
"smiles": "CCn1cc(N2CCN(C(=O)OC(C)(C)C)CC2=O)c2ccc(F)nc21",
"reactionStepId": "sa_b7626b52cf9d7fb95b71d1f2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225602A1;0106;1414812\",\"rsmi\":\"Br[c:5]1[cH:4][n:3]([CH2:2][CH3:1])[c:26]2[c:20]1[cH:21][cH:22][c:23]([F:24])[n:25]2.[NH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]1=[O:19]>C1COCCO1.CNCCNC.O=P(O)(O)O.[Cu]I.[K+].[K+].[K+]>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]2=[O:19])[c:20]2[cH:21][cH:22][c:23]([F:24])[n:25][c:26]12\"},\"mapped_reaction_smiles\":\"Br[c:5]1[cH:4][n:3]([CH2:2][CH3:1])[c:26]2[c:20]1[cH:21][cH:22][c:23]([F:24])[n:25]2.[NH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]1=[O:19]>C1COCCO1.CNCCNC.O=P(O)(O)O.[Cu]I.[K+].[K+].[K+]>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]2=[O:19])[c:20]2[cH:21][cH:22][c:23]([F:24])[n:25][c:26]12\"}",
"reactionStep": {
"id": "sa_b7626b52cf9d7fb95b71d1f2",
"reactionHash": "eb5660ae31f5a7315d958812143cd3161735b4e12dcce83c8d447eea16a1e2ac"
},
"children": [
{
"id": "4901",
"routeId": "sa_265b0924917971a6cbf42183",
"moleculeId": "sa_cfd4e2deeb3e754b4ba9bf2f",
"parentId": "4900",
"isLeaf": true,
"molecule": {
"id": "sa_cfd4e2deeb3e754b4ba9bf2f",
"inchikey": "FCMLWBBLOASUSO-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCNC(=O)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CCNC(=O)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4902",
"routeId": "sa_265b0924917971a6cbf42183",
"moleculeId": "sa_a1e68ac112e06acd88061c5b",
"parentId": "4900",
"isLeaf": false,
"molecule": {
"id": "sa_a1e68ac112e06acd88061c5b",
"inchikey": "VYUMBFFXGMILSC-UHFFFAOYSA-N",
"smiles": "CCn1cc(Br)c2ccc(F)nc21"
},
"smiles": "CCn1cc(Br)c2ccc(F)nc21",
"reactionStepId": "sa_19066a99f252dfc017f00ac6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225602A1;0104;1414811\",\"rsmi\":\"O=C1CCC(=O)N1[Br:6].[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:7]2[cH:8][cH:9][c:10]([F:11])[n:12][c:13]12>CN(C)C=O.[Na+].O>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([Br:6])[c:7]2[cH:8][cH:9][c:10]([F:11])[n:12][c:13]12\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:6].[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:7]2[cH:8][cH:9][c:10]([F:11])[n:12][c:13]12>CN(C)C=O.[Na+].O>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([Br:6])[c:7]2[cH:8][cH:9][c:10]([F:11])[n:12][c:13]12\"}",
"reactionStep": {
"id": "sa_19066a99f252dfc017f00ac6",
"reactionHash": "935ed3b55a1f0b3ba38af29ac174e0b29d68a97dd001957ab04ab5523a3e9dd2"
},
"children": [
{
"id": "4903",
"routeId": "sa_265b0924917971a6cbf42183",
"moleculeId": "sa_d84efda8eda53f699841e337",
"parentId": "4902",
"isLeaf": false,
"molecule": {
"id": "sa_d84efda8eda53f699841e337",
"inchikey": "GARLODZJGNGEIH-UHFFFAOYSA-N",
"smiles": "CCn1ccc2ccc(F)nc21"
},
"smiles": "CCn1ccc2ccc(F)nc21",
"reactionStepId": "sa_613f90703925d1510e39d23b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225602A1;0102;1414810\",\"rsmi\":\"Br[CH2:2][CH3:1].[nH:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9]([F:10])[n:11][c:12]12>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9]([F:10])[n:11][c:12]12\"},\"mapped_reaction_smiles\":\"Br[CH2:2][CH3:1].[nH:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9]([F:10])[n:11][c:12]12>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9]([F:10])[n:11][c:12]12\"}",
"reactionStep": {
"id": "sa_613f90703925d1510e39d23b",
"reactionHash": "dc7971a001c89c777f80c3d9dd18676072dc8c7aed001e8e9f9949f48bd2785e"
},
"children": [
{
"id": "4904",
"routeId": "sa_265b0924917971a6cbf42183",
"moleculeId": "sa_deca38c6d027ae32a2d08282",
"parentId": "4903",
"isLeaf": true,
"molecule": {
"id": "sa_deca38c6d027ae32a2d08282",
"inchikey": "RDHPKYGYEGBMSE-UHFFFAOYSA-N",
"smiles": "CCBr"
},
"smiles": "CCBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4905",
"routeId": "sa_265b0924917971a6cbf42183",
"moleculeId": "sa_7d51886a2d8eb75b5dc3e83a",
"parentId": "4903",
"isLeaf": true,
"molecule": {
"id": "sa_7d51886a2d8eb75b5dc3e83a",
"inchikey": "ZALXIVQPEUDQPO-UHFFFAOYSA-N",
"smiles": "Fc1ccc2cc[nH]c2n1"
},
"smiles": "Fc1ccc2cc[nH]c2n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "4906",
"routeId": "sa_265b0924917971a6cbf42183",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "4902",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
},
{
"id": "4907",
"routeId": "sa_265b0924917971a6cbf42183",
"moleculeId": "sa_786c6159be77bb31e43bff8a",
"parentId": "4896",
"isLeaf": true,
"molecule": {
"id": "sa_786c6159be77bb31e43bff8a",
"inchikey": "XMJHPCRAQCTCFT-UHFFFAOYSA-N",
"smiles": "COC(=O)Cl"
},
"smiles": "COC(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}