Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CSc1nc2ccc(Nc3cc(NC(=O)c4cccc(C(C)(C)C#N)c4)ccc3C)cc2c(=O)n1C
InChiKey
RGKVKDJZIMPEES-UHFFFAOYSA-N
Route Signature
a639436f49abc7bd6eba4bdde513a32a439e9b1244b3438e4c435a46f292f028
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_299f7e18c3e44620111e5e7d",
"signature": "a639436f49abc7bd6eba4bdde513a32a439e9b1244b3438e4c435a46f292f028",
"contentHash": "10b8a34378ba59e14980559fa50ed6c179167fc3a0114c8f9a86ab4dc46fbd1f",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_45a639bf158e7698a48459ad",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-00268",
"moleculeId": "sa_7325a671e68f9752471a7f81",
"smiles": "CSc1nc2ccc(Nc3cc(NC(=O)c4cccc(C(C)(C)C#N)c4)ccc3C)cc2c(=O)n1C",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_7325a671e68f9752471a7f81",
"inchikey": "RGKVKDJZIMPEES-UHFFFAOYSA-N",
"smiles": "CSc1nc2ccc(Nc3cc(NC(=O)c4cccc(C(C)(C)C#N)c4)ccc3C)cc2c(=O)n1C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "529",
"routeId": "sa_299f7e18c3e44620111e5e7d",
"moleculeId": "sa_7325a671e68f9752471a7f81",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7325a671e68f9752471a7f81",
"inchikey": "RGKVKDJZIMPEES-UHFFFAOYSA-N",
"smiles": "CSc1nc2ccc(Nc3cc(NC(=O)c4cccc(C(C)(C)C#N)c4)ccc3C)cc2c(=O)n1C"
},
"smiles": "CSc1nc2ccc(Nc3cc(NC(=O)c4cccc(C(C)(C)C#N)c4)ccc3C)cc2c(=O)n1C",
"reactionStepId": "sa_545776de0879f6dbd9255a69",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118261A1;0274;699622\",\"rsmi\":\"Br[c:8]1[cH:7][cH:6][c:5]2[n:4][c:3]([S:2][CH3:1])[n:35]([CH3:36])[c:33](=[O:34])[c:32]2[cH:31]1.[NH2:9][c:10]1[c:11]([CH3:12])[cH:13][cH:14][c:15]([NH:16][C:17](=[O:18])[c:19]2[cH:20][c:21]([C:22]([CH3:23])([CH3:24])[C:25]#[N:26])[cH:27][cH:28][cH:29]2)[cH:30]1>C1COCCO1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][S:2][c:3]1[n:4][c:5]2[cH:6][cH:7][c:8]([NH:9][c:10]3[c:11]([CH3:12])[cH:13][cH:14][c:15]([NH:16][C:17](=[O:18])[c:19]4[cH:20][c:21]([C:22]([CH3:23])([CH3:24])[C:25]#[N:26])[cH:27][cH:28][cH:29]4)[cH:30]3)[cH:31][c:32]2[c:33](=[O:34])[n:35]1[CH3:36]\"},\"mapped_reaction_smiles\":\"Br[c:8]1[cH:7][cH:6][c:5]2[n:4][c:3]([S:2][CH3:1])[n:35]([CH3:36])[c:33](=[O:34])[c:32]2[cH:31]1.[NH2:9][c:10]1[c:11]([CH3:12])[cH:13][cH:14][c:15]([NH:16][C:17](=[O:18])[c:19]2[cH:20][c:21]([C:22]([CH3:23])([CH3:24])[C:25]#[N:26])[cH:27][cH:28][cH:29]2)[cH:30]1>C1COCCO1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][S:2][c:3]1[n:4][c:5]2[cH:6][cH:7][c:8]([NH:9][c:10]3[c:11]([CH3:12])[cH:13][cH:14][c:15]([NH:16][C:17](=[O:18])[c:19]4[cH:20][c:21]([C:22]([CH3:23])([CH3:24])[C:25]#[N:26])[cH:27][cH:28][cH:29]4)[cH:30]3)[cH:31][c:32]2[c:33](=[O:34])[n:35]1[CH3:36]\"}",
"reactionStep": {
"id": "sa_545776de0879f6dbd9255a69",
"reactionHash": "e71acb96f8c63385c9da21a7f8301ba44f4aa3738c7bad77dd65333c7c229e8b"
},
"children": [
{
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"moleculeId": "sa_34cdca4b58f73e433da61568",
"parentId": "529",
"isLeaf": false,
"molecule": {
"id": "sa_34cdca4b58f73e433da61568",
"inchikey": "TYVHWMWGBLWDBH-UHFFFAOYSA-N",
"smiles": "Cc1ccc(NC(=O)c2cccc(C(C)(C)C#N)c2)cc1N"
},
"smiles": "Cc1ccc(NC(=O)c2cccc(C(C)(C)C#N)c2)cc1N",
"reactionStepId": "sa_7be941c316bf7cbab51c28a8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118261A1;0283;699626\",\"rsmi\":\"O=[N+:4]([O-])[c:3]1[c:2]([CH3:1])[cH:22][cH:21][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[C:16]#[N:17])[cH:18][cH:19][cH:20]2)[cH:5]1>CCO.NN.O.[Pd]>[CH3:1][c:2]1[c:3]([NH2:4])[cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[C:16]#[N:17])[cH:18][cH:19][cH:20]2)[cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"O=[N+:4]([O-])[c:3]1[c:2]([CH3:1])[cH:22][cH:21][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[C:16]#[N:17])[cH:18][cH:19][cH:20]2)[cH:5]1>CCO.NN.O.[Pd]>[CH3:1][c:2]1[c:3]([NH2:4])[cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[C:16]#[N:17])[cH:18][cH:19][cH:20]2)[cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_7be941c316bf7cbab51c28a8",
"reactionHash": "2da4039d9012d13c522a324e40adb3550420df61d437b6dfa92a9f0f34dd625e"
},
"children": [
{
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"moleculeId": "sa_e4908de03990e90534cbd086",
"parentId": "530",
"isLeaf": false,
"molecule": {
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"inchikey": "XIRHXOAKFKJTBC-UHFFFAOYSA-N",
"smiles": "Cc1ccc(NC(=O)c2cccc(C(C)(C)C#N)c2)cc1[N+](=O)[O-]"
},
"smiles": "Cc1ccc(NC(=O)c2cccc(C(C)(C)C#N)c2)cc1[N+](=O)[O-]",
"reactionStepId": "sa_bc409d61b6c46bf612e1df9c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118261A1;0281;699625\",\"rsmi\":\"O[C:10](=[O:11])[c:12]1[cH:13][c:14]([C:15]([CH3:16])([CH3:17])[C:18]#[N:19])[cH:20][cH:21][cH:22]1.[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8]([NH2:9])[cH:23][cH:24]1>CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.ClCCl.On1nnc2ccccc21>[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][c:14]([C:15]([CH3:16])([CH3:17])[C:18]#[N:19])[cH:20][cH:21][cH:22]2)[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"O[C:10](=[O:11])[c:12]1[cH:13][c:14]([C:15]([CH3:16])([CH3:17])[C:18]#[N:19])[cH:20][cH:21][cH:22]1.[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8]([NH2:9])[cH:23][cH:24]1>CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.ClCCl.On1nnc2ccccc21>[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][c:14]([C:15]([CH3:16])([CH3:17])[C:18]#[N:19])[cH:20][cH:21][cH:22]2)[cH:23][cH:24]1\"}",
"reactionStep": {
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"reactionHash": "a0dc8bb8ed8a1b5d3c038d6f796678810f59057c9da3834474970f23a268cf09"
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"children": [
{
"id": "532",
"routeId": "sa_299f7e18c3e44620111e5e7d",
"moleculeId": "sa_1dd4385b1fb845d6dd4ba80b",
"parentId": "531",
"isLeaf": true,
"molecule": {
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"inchikey": "GDIIPKWHAQGCJF-UHFFFAOYSA-N",
"smiles": "Cc1ccc(N)cc1[N+](=O)[O-]"
},
"smiles": "Cc1ccc(N)cc1[N+](=O)[O-]",
"reactionStepId": null,
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},
{
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"parentId": "531",
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"molecule": {
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"inchikey": "VSCTXXVTZNQKAX-UHFFFAOYSA-N",
"smiles": "CC(C)(C#N)c1cccc(C(=O)O)c1"
},
"smiles": "CC(C)(C#N)c1cccc(C(=O)O)c1",
"reactionStepId": "sa_10defba268795e94eac5e9ba",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118261A1;0279;699624\",\"rsmi\":\"C[O:13][C:11]([c:10]1[cH:9][cH:8][cH:7][c:6]([C:2]([CH3:1])([CH3:3])[C:4]#[N:5])[cH:14]1)=[O:12]>C1CCOC1.CO.O.O.[Li+].O>[CH3:1][C:2]([CH3:3])([C:4]#[N:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14]1\"},\"mapped_reaction_smiles\":\"C[O:13][C:11]([c:10]1[cH:9][cH:8][cH:7][c:6]([C:2]([CH3:1])([CH3:3])[C:4]#[N:5])[cH:14]1)=[O:12]>C1CCOC1.CO.O.O.[Li+].O>[CH3:1][C:2]([CH3:3])([C:4]#[N:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14]1\"}",
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"molecule": {
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"inchikey": "FKRJEXVTBGQAMO-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cccc(C(C)(C)C#N)c1"
},
"smiles": "COC(=O)c1cccc(C(C)(C)C#N)c1",
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}
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}
]
},
{
"id": "535",
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"moleculeId": "sa_3987284437da964785d67bc1",
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"molecule": {
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"inchikey": "UBSVWSDJDOKLAS-UHFFFAOYSA-N",
"smiles": "CSc1nc2ccc(Br)cc2c(=O)n1C"
},
"smiles": "CSc1nc2ccc(Br)cc2c(=O)n1C",
"reactionStepId": "sa_7b4bc295a5afa28a394a6e94",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118261A1;0323;699650\",\"rsmi\":\"I[CH3:1].[S:2]=[c:3]1[nH:4][c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][c:11]2[c:12](=[O:13])[n:14]1[CH3:15]>CC(C)=O.[Na+].O>[CH3:1][S:2][c:3]1[n:4][c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][c:11]2[c:12](=[O:13])[n:14]1[CH3:15]\"},\"mapped_reaction_smiles\":\"I[CH3:1].[S:2]=[c:3]1[nH:4][c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][c:11]2[c:12](=[O:13])[n:14]1[CH3:15]>CC(C)=O.[Na+].O>[CH3:1][S:2][c:3]1[n:4][c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][c:11]2[c:12](=[O:13])[n:14]1[CH3:15]\"}",
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{
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"smiles": "Cn1c(=S)[nH]c2ccc(Br)cc2c1=O",
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{
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}
}