Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)(C#N)c1cccc(C(=O)Nc2ccc(C#N)c(NC(=O)c3cc4nccnc4s3)c2)c1
InChiKey
YAFHTLBKJQXDRX-UHFFFAOYSA-N
Route Signature
aa9b8721237e6276aec2dcdf1e8aacc8caa4a22757de0254d4848001d55560af
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_e88e443afac44f4b93768b7b",
"signature": "aa9b8721237e6276aec2dcdf1e8aacc8caa4a22757de0254d4848001d55560af",
"contentHash": "cda678269a754d74305a18772d258f92618f54440ad97acd27fd0d737afb67bd",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_5ae0baea5e6b0e47e3d3b7b8",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02482",
"moleculeId": "sa_ae520bf39c2b7a8b46ddc4ec",
"smiles": "CC(C)(C#N)c1cccc(C(=O)Nc2ccc(C#N)c(NC(=O)c3cc4nccnc4s3)c2)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_ae520bf39c2b7a8b46ddc4ec",
"inchikey": "YAFHTLBKJQXDRX-UHFFFAOYSA-N",
"smiles": "CC(C)(C#N)c1cccc(C(=O)Nc2ccc(C#N)c(NC(=O)c3cc4nccnc4s3)c2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10734",
"routeId": "sa_e88e443afac44f4b93768b7b",
"moleculeId": "sa_ae520bf39c2b7a8b46ddc4ec",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_ae520bf39c2b7a8b46ddc4ec",
"inchikey": "YAFHTLBKJQXDRX-UHFFFAOYSA-N",
"smiles": "CC(C)(C#N)c1cccc(C(=O)Nc2ccc(C#N)c(NC(=O)c3cc4nccnc4s3)c2)c1"
},
"smiles": "CC(C)(C#N)c1cccc(C(=O)Nc2ccc(C#N)c(NC(=O)c3cc4nccnc4s3)c2)c1",
"reactionStepId": "sa_8a78f1961f0a03f72d82e7ec",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130079341A1;0240;1350263\",\"rsmi\":\"Br[c:29]1[c:16]([NH:17][C:18](=[O:19])[c:20]2[cH:21][c:22]3[n:23][cH:24][cH:25][n:26][c:27]3[s:28]2)[cH:15][c:14]([NH:13][C:11]([c:10]2[cH:9][cH:8][cH:7][c:6]([C:2]([CH3:1])([CH3:3])[C:4]#[N:5])[cH:34]2)=[O:12])[cH:33][cH:32]1.[Cu][C:30]#[N:31]>CN1CCCC1=O.Cl.[Cu]I.N>[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])[NH:13][c:14]2[cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]3[cH:21][c:22]4[n:23][cH:24][cH:25][n:26][c:27]4[s:28]3)[c:29]([C:30]#[N:31])[cH:32][cH:33]2)[cH:34]1\"},\"mapped_reaction_smiles\":\"Br[c:29]1[c:16]([NH:17][C:18](=[O:19])[c:20]2[cH:21][c:22]3[n:23][cH:24][cH:25][n:26][c:27]3[s:28]2)[cH:15][c:14]([NH:13][C:11]([c:10]2[cH:9][cH:8][cH:7][c:6]([C:2]([CH3:1])([CH3:3])[C:4]#[N:5])[cH:34]2)=[O:12])[cH:33][cH:32]1.[Cu][C:30]#[N:31]>CN1CCCC1=O.Cl.[Cu]I.N>[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])[NH:13][c:14]2[cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]3[cH:21][c:22]4[n:23][cH:24][cH:25][n:26][c:27]4[s:28]3)[c:29]([C:30]#[N:31])[cH:32][cH:33]2)[cH:34]1\"}",
"reactionStep": {
"id": "sa_8a78f1961f0a03f72d82e7ec",
"reactionHash": "b0ce9c17acfa8a74632760996579d3f7aad00f8508c233370d5f67fc6b6eb017"
},
"children": [
{
"id": "10735",
"routeId": "sa_e88e443afac44f4b93768b7b",
"moleculeId": "sa_e11ca71068ddcf6649aafd11",
"parentId": "10734",
"isLeaf": true,
"molecule": {
"id": "sa_e11ca71068ddcf6649aafd11",
"inchikey": "DULSAGLWMRMKCQ-UHFFFAOYSA-N",
"smiles": "N#[C][Cu]"
},
"smiles": "N#[C][Cu]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10736",
"routeId": "sa_e88e443afac44f4b93768b7b",
"moleculeId": "sa_23d7b919492c9743a785a1fd",
"parentId": "10734",
"isLeaf": false,
"molecule": {
"id": "sa_23d7b919492c9743a785a1fd",
"inchikey": "GXSPOCMEPWOWIM-UHFFFAOYSA-N",
"smiles": "CC(C)(C#N)c1cccc(C(=O)Nc2ccc(Br)c(NC(=O)c3cc4nccnc4s3)c2)c1"
},
"smiles": "CC(C)(C#N)c1cccc(C(=O)Nc2ccc(Br)c(NC(=O)c3cc4nccnc4s3)c2)c1",
"reactionStepId": "sa_9c430df3ca7f6880f09f441f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130079341A1;0238;1350262\",\"rsmi\":\"Cl[C:18](=[O:19])[c:20]1[cH:21][c:22]2[n:23][cH:24][cH:25][n:26][c:27]2[s:28]1.[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])[NH:13][c:14]2[cH:15][c:16]([NH2:17])[c:29]([Br:30])[cH:31][cH:32]2)[cH:33]1>C1COCCO1.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])[NH:13][c:14]2[cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]3[cH:21][c:22]4[n:23][cH:24][cH:25][n:26][c:27]4[s:28]3)[c:29]([Br:30])[cH:31][cH:32]2)[cH:33]1\"},\"mapped_reaction_smiles\":\"Cl[C:18](=[O:19])[c:20]1[cH:21][c:22]2[n:23][cH:24][cH:25][n:26][c:27]2[s:28]1.[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])[NH:13][c:14]2[cH:15][c:16]([NH2:17])[c:29]([Br:30])[cH:31][cH:32]2)[cH:33]1>C1COCCO1.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])[NH:13][c:14]2[cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]3[cH:21][c:22]4[n:23][cH:24][cH:25][n:26][c:27]4[s:28]3)[c:29]([Br:30])[cH:31][cH:32]2)[cH:33]1\"}",
"reactionStep": {
"id": "sa_9c430df3ca7f6880f09f441f",
"reactionHash": "1c69d4d94d7c36b2c2767dc25d2478c8bd5f27ab12b0110a386eb9415287a8e3"
},
"children": [
{
"id": "10737",
"routeId": "sa_e88e443afac44f4b93768b7b",
"moleculeId": "sa_02e30ba7cbdc93500b779d8e",
"parentId": "10736",
"isLeaf": false,
"molecule": {
"id": "sa_02e30ba7cbdc93500b779d8e",
"inchikey": "IIIIXAGTGQZLQL-UHFFFAOYSA-N",
"smiles": "CC(C)(C#N)c1cccc(C(=O)Nc2ccc(Br)c(N)c2)c1"
},
"smiles": "CC(C)(C#N)c1cccc(C(=O)Nc2ccc(Br)c(N)c2)c1",
"reactionStepId": "sa_af26abd22a283933a5f219bb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130079341A1;0236;1350260\",\"rsmi\":\"O=[N+:17]([O-])[c:16]1[cH:15][c:14]([NH:13][C:11]([c:10]2[cH:9][cH:8][cH:7][c:6]([C:2]([CH3:1])([CH3:3])[C:4]#[N:5])[cH:22]2)=[O:12])[cH:21][cH:20][c:18]1[Br:19]>C1CCOC1.CC#N.CC(=O)O.CCO.[Zn]>[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])[NH:13][c:14]2[cH:15][c:16]([NH2:17])[c:18]([Br:19])[cH:20][cH:21]2)[cH:22]1\"},\"mapped_reaction_smiles\":\"O=[N+:17]([O-])[c:16]1[cH:15][c:14]([NH:13][C:11]([c:10]2[cH:9][cH:8][cH:7][c:6]([C:2]([CH3:1])([CH3:3])[C:4]#[N:5])[cH:22]2)=[O:12])[cH:21][cH:20][c:18]1[Br:19]>C1CCOC1.CC#N.CC(=O)O.CCO.[Zn]>[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])[NH:13][c:14]2[cH:15][c:16]([NH2:17])[c:18]([Br:19])[cH:20][cH:21]2)[cH:22]1\"}",
"reactionStep": {
"id": "sa_af26abd22a283933a5f219bb",
"reactionHash": "bd1ef54b1e81e71b26c95b40b91e8c4850307ec1c6dbb906635bc679ebc0f5ce"
},
"children": [
{
"id": "10738",
"routeId": "sa_e88e443afac44f4b93768b7b",
"moleculeId": "sa_2338c4f55db1f72b9b1caa39",
"parentId": "10737",
"isLeaf": false,
"molecule": {
"id": "sa_2338c4f55db1f72b9b1caa39",
"inchikey": "WJMLJNRJXAQUMD-UHFFFAOYSA-N",
"smiles": "CC(C)(C#N)c1cccc(C(=O)Nc2ccc(Br)c([N+](=O)[O-])c2)c1"
},
"smiles": "CC(C)(C#N)c1cccc(C(=O)Nc2ccc(Br)c([N+](=O)[O-])c2)c1",
"reactionStepId": "sa_d0ba2d9827beb48f4e978e95",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130079341A1;0235;1350259\",\"rsmi\":\"O[C:11]([c:10]1[cH:9][cH:8][cH:7][c:6]([C:2]([CH3:1])([CH3:3])[C:4]#[N:5])[cH:24]1)=[O:12].[NH2:13][c:14]1[cH:15][c:16]([N+:17](=[O:18])[O-:19])[c:20]([Br:21])[cH:22][cH:23]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[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])[NH:13][c:14]2[cH:15][c:16]([N+:17](=[O:18])[O-:19])[c:20]([Br:21])[cH:22][cH:23]2)[cH:24]1\"},\"mapped_reaction_smiles\":\"O[C:11]([c:10]1[cH:9][cH:8][cH:7][c:6]([C:2]([CH3:1])([CH3:3])[C:4]#[N:5])[cH:24]1)=[O:12].[NH2:13][c:14]1[cH:15][c:16]([N+:17](=[O:18])[O-:19])[c:20]([Br:21])[cH:22][cH:23]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[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])[NH:13][c:14]2[cH:15][c:16]([N+:17](=[O:18])[O-:19])[c:20]([Br:21])[cH:22][cH:23]2)[cH:24]1\"}",
"reactionStep": {
"id": "sa_d0ba2d9827beb48f4e978e95",
"reactionHash": "f90f7d627c0170459fa58c6c911a20492507da3ca67d6d0955f260d925378124"
},
"children": [
{
"id": "10739",
"routeId": "sa_e88e443afac44f4b93768b7b",
"moleculeId": "sa_f7f0572f9b15880b64d64c4b",
"parentId": "10738",
"isLeaf": true,
"molecule": {
"id": "sa_f7f0572f9b15880b64d64c4b",
"inchikey": "PITHQPMZWKZGRZ-UHFFFAOYSA-N",
"smiles": "Nc1ccc(Br)c([N+](=O)[O-])c1"
},
"smiles": "Nc1ccc(Br)c([N+](=O)[O-])c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10740",
"routeId": "sa_e88e443afac44f4b93768b7b",
"moleculeId": "sa_2a4610d98e84cd618aec9dd6",
"parentId": "10738",
"isLeaf": false,
"molecule": {
"id": "sa_2a4610d98e84cd618aec9dd6",
"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\":\"US20130079341A1;0106;1350200\",\"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.[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.[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\"}",
"reactionStep": {
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"reactionHash": "f426377396cd496890414db07c18c532babb499bbfdb07a4f5784e825e77f97a"
},
"children": [
{
"id": "10741",
"routeId": "sa_e88e443afac44f4b93768b7b",
"moleculeId": "sa_a4ad521eb59fd45d37659a51",
"parentId": "10740",
"isLeaf": true,
"molecule": {
"id": "sa_a4ad521eb59fd45d37659a51",
"inchikey": "FKRJEXVTBGQAMO-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cccc(C(C)(C)C#N)c1"
},
"smiles": "COC(=O)c1cccc(C(C)(C)C#N)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
]
},
{
"id": "10742",
"routeId": "sa_e88e443afac44f4b93768b7b",
"moleculeId": "sa_8519cc8d56f837ef2c9cd8d8",
"parentId": "10736",
"isLeaf": false,
"molecule": {
"id": "sa_8519cc8d56f837ef2c9cd8d8",
"inchikey": "XWWOVEPEKBJJKO-UHFFFAOYSA-N",
"smiles": "O=C(Cl)c1cc2nccnc2s1"
},
"smiles": "O=C(Cl)c1cc2nccnc2s1",
"reactionStepId": "sa_614ab58aadd5049b7e5b10d6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130079341A1;0237;1350261\",\"rsmi\":\"O=S(Cl)[Cl:3].O[C:2](=[O:1])[c:4]1[cH:5][c:6]2[n:7][cH:8][cH:9][n:10][c:11]2[s:12]1>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][c:6]2[n:7][cH:8][cH:9][n:10][c:11]2[s:12]1\"},\"mapped_reaction_smiles\":\"O=S(Cl)[Cl:3].O[C:2](=[O:1])[c:4]1[cH:5][c:6]2[n:7][cH:8][cH:9][n:10][c:11]2[s:12]1>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][c:6]2[n:7][cH:8][cH:9][n:10][c:11]2[s:12]1\"}",
"reactionStep": {
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"reactionHash": "6d1a7418c0d2dd99d4e5d1b2adbf61f94f261c165255c745a4156b8b871fb635"
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"children": [
{
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"moleculeId": "sa_cd67ce42f230ef1a4063353c",
"parentId": "10742",
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"molecule": {
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"inchikey": "FYSNRJHAOHDILO-UHFFFAOYSA-N",
"smiles": "O=S(Cl)Cl"
},
"smiles": "O=S(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "10744",
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"molecule": {
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"inchikey": "MEHCDDSVVYRWJT-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cc2nccnc2s1"
},
"smiles": "O=C(O)c1cc2nccnc2s1",
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}
]
}
]
}
]
}
}