Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN1C[C@H]2CCN(c3ccc(N4CCN(c5ccc(Cl)nn5)CC4)cc3)[C@H]2C1
InChiKey
UPILQXMDPFUTJP-APWZRJJASA-N
Route Signature
8e2c3e17704a58048b0df0e4c35d703275f882013dbe42a5ddda64dbafedde29
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_678f770d8bdf4f835ea8b1a4",
"signature": "8e2c3e17704a58048b0df0e4c35d703275f882013dbe42a5ddda64dbafedde29",
"contentHash": "18273e6cbedb856b9510093f35413c7eecf599cda4feb8593e2f429d9acef31f",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_944a71efd2d77189d28888bb",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00600",
"moleculeId": "sa_32f2bd443ac0bb35aaa428a3",
"smiles": "CN1C[C@H]2CCN(c3ccc(N4CCN(c5ccc(Cl)nn5)CC4)cc3)[C@H]2C1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_32f2bd443ac0bb35aaa428a3",
"inchikey": "UPILQXMDPFUTJP-APWZRJJASA-N",
"smiles": "CN1C[C@H]2CCN(c3ccc(N4CCN(c5ccc(Cl)nn5)CC4)cc3)[C@H]2C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "4546",
"routeId": "sa_678f770d8bdf4f835ea8b1a4",
"moleculeId": "sa_32f2bd443ac0bb35aaa428a3",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_32f2bd443ac0bb35aaa428a3",
"inchikey": "UPILQXMDPFUTJP-APWZRJJASA-N",
"smiles": "CN1C[C@H]2CCN(c3ccc(N4CCN(c5ccc(Cl)nn5)CC4)cc3)[C@H]2C1"
},
"smiles": "CN1C[C@H]2CCN(c3ccc(N4CCN(c5ccc(Cl)nn5)CC4)cc3)[C@H]2C1",
"reactionStepId": "sa_c1bfa4d6a2a272b19e0d7966",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08399468B2;0375;1295576\",\"rsmi\":\"Cl[c:16]1[cH:17][cH:18][c:19]([Cl:20])[n:21][n:22]1.[CH3:1][N:2]1[CH2:3][C@H:4]2[CH2:5][CH2:6][N:7]([c:8]3[cH:9][cH:10][c:11]([N:12]4[CH2:13][CH2:14][NH:15][CH2:23][CH2:24]4)[cH:25][cH:26]3)[C@H:27]2[CH2:28]1>CC#N.CCN(CC)CC>[CH3:1][N:2]1[CH2:3][C@H:4]2[CH2:5][CH2:6][N:7]([c:8]3[cH:9][cH:10][c:11]([N:12]4[CH2:13][CH2:14][N:15]([c:16]5[cH:17][cH:18][c:19]([Cl:20])[n:21][n:22]5)[CH2:23][CH2:24]4)[cH:25][cH:26]3)[C@H:27]2[CH2:28]1\"},\"mapped_reaction_smiles\":\"Cl[c:16]1[cH:17][cH:18][c:19]([Cl:20])[n:21][n:22]1.[CH3:1][N:2]1[CH2:3][C@H:4]2[CH2:5][CH2:6][N:7]([c:8]3[cH:9][cH:10][c:11]([N:12]4[CH2:13][CH2:14][NH:15][CH2:23][CH2:24]4)[cH:25][cH:26]3)[C@H:27]2[CH2:28]1>CC#N.CCN(CC)CC>[CH3:1][N:2]1[CH2:3][C@H:4]2[CH2:5][CH2:6][N:7]([c:8]3[cH:9][cH:10][c:11]([N:12]4[CH2:13][CH2:14][N:15]([c:16]5[cH:17][cH:18][c:19]([Cl:20])[n:21][n:22]5)[CH2:23][CH2:24]4)[cH:25][cH:26]3)[C@H:27]2[CH2:28]1\"}",
"reactionStep": {
"id": "sa_c1bfa4d6a2a272b19e0d7966",
"reactionHash": "3d5af52e01ca7f1d103b09f0384f941a1ad4ab974f7ba6349166a8410e413364"
},
"children": [
{
"id": "4547",
"routeId": "sa_678f770d8bdf4f835ea8b1a4",
"moleculeId": "sa_d426f4f999390ebabedeebdb",
"parentId": "4546",
"isLeaf": true,
"molecule": {
"id": "sa_d426f4f999390ebabedeebdb",
"inchikey": "GUSWJGOYDXFJSI-UHFFFAOYSA-N",
"smiles": "Clc1ccc(Cl)nn1"
},
"smiles": "Clc1ccc(Cl)nn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4548",
"routeId": "sa_678f770d8bdf4f835ea8b1a4",
"moleculeId": "sa_e0a9282bb26f5fa4426204dc",
"parentId": "4546",
"isLeaf": false,
"molecule": {
"id": "sa_e0a9282bb26f5fa4426204dc",
"inchikey": "XOENLTLPMSUWIS-PBHICJAKSA-N",
"smiles": "CN1C[C@H]2CCN(c3ccc(N4CCNCC4)cc3)[C@H]2C1"
},
"smiles": "CN1C[C@H]2CCN(c3ccc(N4CCNCC4)cc3)[C@H]2C1",
"reactionStepId": "sa_caee20168c23f6367606a17b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08399468B2;0374;1295575\",\"rsmi\":\"CC(=O)[N:15]1[CH2:14][CH2:13][N:12]([c:11]2[cH:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][C@@H:4]4[CH2:3][N:2]([CH3:1])[CH2:21][C@@H:20]43)[cH:19][cH:18]2)[CH2:17][CH2:16]1>CO.Cl>[CH3:1][N:2]1[CH2:3][C@H:4]2[CH2:5][CH2:6][N:7]([c:8]3[cH:9][cH:10][c:11]([N:12]4[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]4)[cH:18][cH:19]3)[C@H:20]2[CH2:21]1\"},\"mapped_reaction_smiles\":\"CC(=O)[N:15]1[CH2:14][CH2:13][N:12]([c:11]2[cH:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][C@@H:4]4[CH2:3][N:2]([CH3:1])[CH2:21][C@@H:20]43)[cH:19][cH:18]2)[CH2:17][CH2:16]1>CO.Cl>[CH3:1][N:2]1[CH2:3][C@H:4]2[CH2:5][CH2:6][N:7]([c:8]3[cH:9][cH:10][c:11]([N:12]4[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]4)[cH:18][cH:19]3)[C@H:20]2[CH2:21]1\"}",
"reactionStep": {
"id": "sa_caee20168c23f6367606a17b",
"reactionHash": "2c0488a65273bcf038bfdd60e0e0888cf46cb96eff1f963605b5547f2c02b569"
},
"children": [
{
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"moleculeId": "sa_8f4e2713d9f75d63e7fbfc2d",
"parentId": "4548",
"isLeaf": false,
"molecule": {
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"inchikey": "IERNINQGJXFZOF-APWZRJJASA-N",
"smiles": "CC(=O)N1CCN(c2ccc(N3CC[C@@H]4CN(C)C[C@@H]43)cc2)CC1"
},
"smiles": "CC(=O)N1CCN(c2ccc(N3CC[C@@H]4CN(C)C[C@@H]43)cc2)CC1",
"reactionStepId": "sa_655e11d7b58c8a8c735ef3ed",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08399468B2;0373;1295574\",\"rsmi\":\"Br[c:8]1[cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][C@@H:15]3[CH2:16][N:17]([CH3:18])[CH2:19][C@H:20]23)[cH:21][cH:22]1.[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][NH:7][CH2:23][CH2:24]1>CC(C)(C)O.Cc1ccccc1.O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([N:12]3[CH2:13][CH2:14][C@@H:15]4[CH2:16][N:17]([CH3:18])[CH2:19][C@H:20]34)[cH:21][cH:22]2)[CH2:23][CH2:24]1\"},\"mapped_reaction_smiles\":\"Br[c:8]1[cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][C@@H:15]3[CH2:16][N:17]([CH3:18])[CH2:19][C@H:20]23)[cH:21][cH:22]1.[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][NH:7][CH2:23][CH2:24]1>CC(C)(C)O.Cc1ccccc1.O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([N:12]3[CH2:13][CH2:14][C@@H:15]4[CH2:16][N:17]([CH3:18])[CH2:19][C@H:20]34)[cH:21][cH:22]2)[CH2:23][CH2:24]1\"}",
"reactionStep": {
"id": "sa_655e11d7b58c8a8c735ef3ed",
"reactionHash": "d9de2c1a5e29986f10939c64c074def1664db62db1cf9605a0021e289a823c0c"
},
"children": [
{
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"routeId": "sa_678f770d8bdf4f835ea8b1a4",
"moleculeId": "sa_02da6e4793c9cf869266d9f3",
"parentId": "4549",
"isLeaf": false,
"molecule": {
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"inchikey": "JQFMTRCQEFPEMJ-MFKMUULPSA-N",
"smiles": "CN1C[C@H]2CCN(c3ccc(Br)cc3)[C@H]2C1"
},
"smiles": "CN1C[C@H]2CCN(c3ccc(Br)cc3)[C@H]2C1",
"reactionStepId": "sa_5b6f792da3d8e932201ac906",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08399468B2;0352;1295563\",\"rsmi\":\"Br[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1.[CH3:1][N:2]1[CH2:3][C@H:4]2[CH2:5][CH2:6][NH:7][C@H:15]2[CH2:16]1>CC(C)(C)O.Cc1ccccc1.O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][N:2]1[CH2:3][C@H:4]2[CH2:5][CH2:6][N:7]([c:8]3[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]3)[C@H:15]2[CH2:16]1\"},\"mapped_reaction_smiles\":\"Br[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1.[CH3:1][N:2]1[CH2:3][C@H:4]2[CH2:5][CH2:6][NH:7][C@H:15]2[CH2:16]1>CC(C)(C)O.Cc1ccccc1.O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][N:2]1[CH2:3][C@H:4]2[CH2:5][CH2:6][N:7]([c:8]3[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]3)[C@H:15]2[CH2:16]1\"}",
"reactionStep": {
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"reactionHash": "fd42e18eb6404a8c78be6b194b65da111375d2d609b5e43dbc87a6819c3b463f"
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"children": [
{
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"routeId": "sa_678f770d8bdf4f835ea8b1a4",
"moleculeId": "sa_2804df6ab87cba9d53644758",
"parentId": "4550",
"isLeaf": false,
"molecule": {
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"inchikey": "DLUDAUJQMXTXGQ-RQJHMYQMSA-N",
"smiles": "CN1C[C@H]2CCN[C@H]2C1"
},
"smiles": "CN1C[C@H]2CCN[C@H]2C1",
"reactionStepId": "sa_df6d5bbac7603d3b4f0cf547",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08399468B2;0351;1295562\",\"rsmi\":\"CC(C)(C)OC(=O)[N:7]1[CH2:6][CH2:5][C@@H:4]2[CH2:3][N:2]([CH3:1])[CH2:9][C@@H:8]21>CO.Cl>[CH3:1][N:2]1[CH2:3][C@H:4]2[CH2:5][CH2:6][NH:7][C@H:8]2[CH2:9]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:7]1[CH2:6][CH2:5][C@@H:4]2[CH2:3][N:2]([CH3:1])[CH2:9][C@@H:8]21>CO.Cl>[CH3:1][N:2]1[CH2:3][C@H:4]2[CH2:5][CH2:6][NH:7][C@H:8]2[CH2:9]1\"}",
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{
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{
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{
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]
}
}