Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1ccccc1Nc1ccc2c(-c3ccccc3)nn(C(=O)OC(C)(C)C)c2c1
InChiKey
LOSSUVVYVGLPPB-UHFFFAOYSA-N
Route Signature
1f99b4825abf444af51659a4caed65445c938e9062b7890ae1e4bbc8871e0cfe
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_0a66b43c29de4b363424a4c5",
"signature": "1f99b4825abf444af51659a4caed65445c938e9062b7890ae1e4bbc8871e0cfe",
"contentHash": "7d77ff3fde4da9a7de67b8414dc0f5bd68de3a087c5e0e0888f0987aea0e6619",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_d03c80a48d1baa335f1714cc",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00404",
"moleculeId": "sa_b869a0db6cb821e11ab8ee3d",
"smiles": "COc1ccccc1Nc1ccc2c(-c3ccccc3)nn(C(=O)OC(C)(C)C)c2c1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_b869a0db6cb821e11ab8ee3d",
"inchikey": "LOSSUVVYVGLPPB-UHFFFAOYSA-N",
"smiles": "COc1ccccc1Nc1ccc2c(-c3ccccc3)nn(C(=O)OC(C)(C)C)c2c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 3
},
"rootNode": {
"id": "4200",
"routeId": "sa_0a66b43c29de4b363424a4c5",
"moleculeId": "sa_b869a0db6cb821e11ab8ee3d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_b869a0db6cb821e11ab8ee3d",
"inchikey": "LOSSUVVYVGLPPB-UHFFFAOYSA-N",
"smiles": "COc1ccccc1Nc1ccc2c(-c3ccccc3)nn(C(=O)OC(C)(C)C)c2c1"
},
"smiles": "COc1ccccc1Nc1ccc2c(-c3ccccc3)nn(C(=O)OC(C)(C)C)c2c1",
"reactionStepId": "sa_4f1f72d78412339bee2f905b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050113370A1;0192;253432\",\"rsmi\":\"Br[c:4]1[c:3]([O:2][CH3:1])[cH:31][cH:30][cH:29][cH:28]1.[NH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[n:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][c:21]2-[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11]2)[n:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][c:21]3-[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28][cH:29][cH:30][cH:31]1\"},\"mapped_reaction_smiles\":\"Br[c:4]1[c:3]([O:2][CH3:1])[cH:31][cH:30][cH:29][cH:28]1.[NH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[n:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][c:21]2-[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11]2)[n:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][c:21]3-[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28][cH:29][cH:30][cH:31]1\"}",
"reactionStep": {
"id": "sa_4f1f72d78412339bee2f905b",
"reactionHash": "44379f36cc7cfeffcf64cdb08dab65a00edb2f55b81dd979625154fa14bc9fd7"
},
"children": [
{
"id": "4201",
"routeId": "sa_0a66b43c29de4b363424a4c5",
"moleculeId": "sa_d06a7955e1ed9d55a27d1936",
"parentId": "4200",
"isLeaf": true,
"molecule": {
"id": "sa_d06a7955e1ed9d55a27d1936",
"inchikey": "HTDQSWDEWGSAMN-UHFFFAOYSA-N",
"smiles": "COc1ccccc1Br"
},
"smiles": "COc1ccccc1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4202",
"routeId": "sa_0a66b43c29de4b363424a4c5",
"moleculeId": "sa_c26b0a6af9d7051e33ae1dc7",
"parentId": "4200",
"isLeaf": false,
"molecule": {
"id": "sa_c26b0a6af9d7051e33ae1dc7",
"inchikey": "RBYDEPOIPYYEDS-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)n1nc(-c2ccccc2)c2ccc(N)cc21"
},
"smiles": "CC(C)(C)OC(=O)n1nc(-c2ccccc2)c2ccc(N)cc21",
"reactionStepId": "sa_54cde7a25378675d175a7a4a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050113370A1;0168;253422\",\"rsmi\":\"O=[N+:21]([O-])[c:20]1[cH:19][cH:18][c:17]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:9][n:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:23]2[cH:22]1>C1CCOC1.CCO.CCOC(C)=O.O=[Pt]=O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][c:20]([NH2:21])[cH:22][c:23]12\"},\"mapped_reaction_smiles\":\"O=[N+:21]([O-])[c:20]1[cH:19][cH:18][c:17]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:9][n:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:23]2[cH:22]1>C1CCOC1.CCO.CCOC(C)=O.O=[Pt]=O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][c:20]([NH2:21])[cH:22][c:23]12\"}",
"reactionStep": {
"id": "sa_54cde7a25378675d175a7a4a",
"reactionHash": "067d6ac02d7e8f44ff2ce4e9022fc0792ef2ab6eb0a9932e003e2340a9fb4d86"
},
"children": [
{
"id": "4203",
"routeId": "sa_0a66b43c29de4b363424a4c5",
"moleculeId": "sa_1534eefaade8386fa721a074",
"parentId": "4202",
"isLeaf": false,
"molecule": {
"id": "sa_1534eefaade8386fa721a074",
"inchikey": "FFXWUKMQSVZFCV-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)n1nc(-c2ccccc2)c2ccc([N+](=O)[O-])cc21"
},
"smiles": "CC(C)(C)OC(=O)n1nc(-c2ccccc2)c2ccc([N+](=O)[O-])cc21",
"reactionStepId": "sa_bfdac1a6a37ffc1acceb646a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050113370A1;0167;253421\",\"rsmi\":\"I[c:10]1[n:9][n:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:25]2[c:17]1[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24]2.OB(O)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>CCO.Cc1ccccc1.ClCCl.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][c:25]12\"},\"mapped_reaction_smiles\":\"I[c:10]1[n:9][n:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:25]2[c:17]1[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24]2.OB(O)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>CCO.Cc1ccccc1.ClCCl.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][c:25]12\"}",
"reactionStep": {
"id": "sa_bfdac1a6a37ffc1acceb646a",
"reactionHash": "70c9ef8151ce0ae612d96ff1aae09e2e164ca7c67d5d32eab26ece8f52131fd2"
},
"children": [
{
"id": "4204",
"routeId": "sa_0a66b43c29de4b363424a4c5",
"moleculeId": "sa_05364e99571ecb363666a42f",
"parentId": "4203",
"isLeaf": true,
"molecule": {
"id": "sa_05364e99571ecb363666a42f",
"inchikey": "HXITXNWTGFUOAU-UHFFFAOYSA-N",
"smiles": "OB(O)c1ccccc1"
},
"smiles": "OB(O)c1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4205",
"routeId": "sa_0a66b43c29de4b363424a4c5",
"moleculeId": "sa_48a94f58de7991b9866a6c0c",
"parentId": "4203",
"isLeaf": false,
"molecule": {
"id": "sa_48a94f58de7991b9866a6c0c",
"inchikey": "LDINLYRPDJPXTG-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)n1nc(I)c2ccc([N+](=O)[O-])cc21"
},
"smiles": "CC(C)(C)OC(=O)n1nc(I)c2ccc([N+](=O)[O-])cc21",
"reactionStepId": "sa_bf30990d6180c8dfe6ea5f5c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050113370A1;0166;253420\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[nH:8]1[n:9][c:10]([I:11])[c:12]2[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]12>CC#N.CCN(CC)CC.CN(C)c1ccncc1.CO.ClCCl.O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[n:9][c:10]([I:11])[c:12]2[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]12\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[nH:8]1[n:9][c:10]([I:11])[c:12]2[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]12>CC#N.CCN(CC)CC.CN(C)c1ccncc1.CO.ClCCl.O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[n:9][c:10]([I:11])[c:12]2[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]12\"}",
"reactionStep": {
"id": "sa_bf30990d6180c8dfe6ea5f5c",
"reactionHash": "79648d694e35f6bec8088e42e12869e090f2b70c49807b45df98806e5443b1de"
},
"children": [
{
"id": "4206",
"routeId": "sa_0a66b43c29de4b363424a4c5",
"moleculeId": "sa_b273d4d4546165bca2b249b5",
"parentId": "4205",
"isLeaf": true,
"molecule": {
"id": "sa_b273d4d4546165bca2b249b5",
"inchikey": "DYHSDKLCOJIUFX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C"
},
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4207",
"routeId": "sa_0a66b43c29de4b363424a4c5",
"moleculeId": "sa_7a14491dcc6ef49e907e64dd",
"parentId": "4205",
"isLeaf": false,
"molecule": {
"id": "sa_7a14491dcc6ef49e907e64dd",
"inchikey": "GZCGNGLOCQEDMT-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc2c(I)[nH]nc2c1"
},
"smiles": "O=[N+]([O-])c1ccc2c(I)n[nH]c2c1",
"reactionStepId": "sa_c06e7c3fb4ca1356742c54c1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050113370A1;0165;253419\",\"rsmi\":\"I[I:13].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[nH:10][n:11][cH:12]2>CN(C)C=O.O=S(O)O.[K+].[Na+].O>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[nH:10][n:11][c:12]2[I:13]\"},\"mapped_reaction_smiles\":\"I[I:13].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[nH:10][n:11][cH:12]2>CN(C)C=O.O=S(O)O.[K+].[Na+].O>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[nH:10][n:11][c:12]2[I:13]\"}",
"reactionStep": {
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"reactionHash": "7220f26b53a2513375fa5776c8ef31b276d0e3556511e3a8774ca872e33f03e5"
},
"children": [
{
"id": "4208",
"routeId": "sa_0a66b43c29de4b363424a4c5",
"moleculeId": "sa_0b83af61e01ccf8e3fd7590d",
"parentId": "4207",
"isLeaf": true,
"molecule": {
"id": "sa_0b83af61e01ccf8e3fd7590d",
"inchikey": "ORZRMRUXSPNQQL-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc2cn[nH]c2c1"
},
"smiles": "O=[N+]([O-])c1ccc2cn[nH]c2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "4209",
"routeId": "sa_0a66b43c29de4b363424a4c5",
"moleculeId": "sa_bc6c113460696c6012e3bdf5",
"parentId": "4207",
"isLeaf": true,
"molecule": {
"id": "sa_bc6c113460696c6012e3bdf5",
"inchikey": "PNDPGZBMCMUPRI-UHFFFAOYSA-N",
"smiles": "II"
},
"smiles": "II",
"reactionStepId": null,
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}
]
}
]
}
]
}
]
}
]
}
}