Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Nc1ncc(-c2ccc(C(=O)N3CCNCC3)cc2)nc1-c1nc2cnccc2o1
InChiKey
LXDMEIDOEIYLGN-UHFFFAOYSA-N
Route Signature
5449b962150e5edf058faf0ee66feff7a650edf85e2f05c1ba37bd25f366f8f6
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_7d2058340ec2a52c7b8d4995",
"signature": "5449b962150e5edf058faf0ee66feff7a650edf85e2f05c1ba37bd25f366f8f6",
"contentHash": "563af634f1eaa609a10fdeaeb1e6e42cd03bc110234052f69e6848c567795a1d",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_6f9fc6c4e534d9be0db81ecc",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01069",
"moleculeId": "sa_1f4f5f5a51b0e62eb01c311c",
"smiles": "Nc1ncc(-c2ccc(C(=O)N3CCNCC3)cc2)nc1-c1nc2cnccc2o1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_1f4f5f5a51b0e62eb01c311c",
"inchikey": "LXDMEIDOEIYLGN-UHFFFAOYSA-N",
"smiles": "Nc1ncc(-c2ccc(C(=O)N3CCNCC3)cc2)nc1-c1nc2cnccc2o1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "5254",
"routeId": "sa_7d2058340ec2a52c7b8d4995",
"moleculeId": "sa_1f4f5f5a51b0e62eb01c311c",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_1f4f5f5a51b0e62eb01c311c",
"inchikey": "LXDMEIDOEIYLGN-UHFFFAOYSA-N",
"smiles": "Nc1ncc(-c2ccc(C(=O)N3CCNCC3)cc2)nc1-c1nc2cnccc2o1"
},
"smiles": "Nc1ncc(-c2ccc(C(=O)N3CCNCC3)cc2)nc1-c1nc2cnccc2o1",
"reactionStepId": "sa_7d3a5f7f837c9ca12eeb7c1f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110118275A1;0200;1056689\",\"rsmi\":\"CC(C)(C)OC(=O)[N:24]1[CH2:23][CH2:22][N:21]([C:19]([c:18]2[cH:17][cH:16][c:15](-[c:14]3[n:13][c:3](-[c:4]4[n:5][c:6]5[c:7]([cH:8][cH:9][n:10][cH:11]5)[o:12]4)[c:2]([NH2:1])[n:30][cH:29]3)[cH:28][cH:27]2)=[O:20])[CH2:26][CH2:25]1>CO.ClCCl.O=C(O)C(F)(F)F>[NH2:1][c:2]1[c:3](-[c:4]2[n:5][c:6]3[c:7]([cH:8][cH:9][n:10][cH:11]3)[o:12]2)[n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([C:19](=[O:20])[N:21]3[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]3)[cH:27][cH:28]2)[cH:29][n:30]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:24]1[CH2:23][CH2:22][N:21]([C:19]([c:18]2[cH:17][cH:16][c:15](-[c:14]3[n:13][c:3](-[c:4]4[n:5][c:6]5[c:7]([cH:8][cH:9][n:10][cH:11]5)[o:12]4)[c:2]([NH2:1])[n:30][cH:29]3)[cH:28][cH:27]2)=[O:20])[CH2:26][CH2:25]1>CO.ClCCl.O=C(O)C(F)(F)F>[NH2:1][c:2]1[c:3](-[c:4]2[n:5][c:6]3[c:7]([cH:8][cH:9][n:10][cH:11]3)[o:12]2)[n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([C:19](=[O:20])[N:21]3[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]3)[cH:27][cH:28]2)[cH:29][n:30]1\"}",
"reactionStep": {
"id": "sa_7d3a5f7f837c9ca12eeb7c1f",
"reactionHash": "5352994340a2b459afb44f2071cab5ac7e36df0fb6a6b8a1a2d4d6641c06de23"
},
"children": [
{
"id": "5255",
"routeId": "sa_7d2058340ec2a52c7b8d4995",
"moleculeId": "sa_cce6416e109f4f44f640e001",
"parentId": "5254",
"isLeaf": false,
"molecule": {
"id": "sa_cce6416e109f4f44f640e001",
"inchikey": "WMDHUGGFIIQAJV-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCN(C(=O)c2ccc(-c3cnc(N)c(-c4nc5cnccc5o4)n3)cc2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCN(C(=O)c2ccc(-c3cnc(N)c(-c4nc5cnccc5o4)n3)cc2)CC1",
"reactionStepId": "sa_a122c11534f15a35f54503dd",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110118275A1;0144;1056681\",\"rsmi\":\"Br[c:18]1[n:19][c:20](-[c:21]2[n:22][c:23]3[c:24]([cH:25][cH:26][n:27][cH:28]3)[o:29]2)[c:30]([NH2:31])[n:32][cH:33]1.CC1(C)OB([c:17]2[cH:16][cH:15][c:14]([C:12]([N:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:37][CH2:36]3)=[O:13])[cH:35][cH:34]2)OC1(C)C>C1CCOC1.O=C(O)O.[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][c:17](-[c:18]3[n:19][c:20](-[c:21]4[n:22][c:23]5[c:24]([cH:25][cH:26][n:27][cH:28]5)[o:29]4)[c:30]([NH2:31])[n:32][cH:33]3)[cH:34][cH:35]2)[CH2:36][CH2:37]1\"},\"mapped_reaction_smiles\":\"Br[c:18]1[n:19][c:20](-[c:21]2[n:22][c:23]3[c:24]([cH:25][cH:26][n:27][cH:28]3)[o:29]2)[c:30]([NH2:31])[n:32][cH:33]1.CC1(C)OB([c:17]2[cH:16][cH:15][c:14]([C:12]([N:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:37][CH2:36]3)=[O:13])[cH:35][cH:34]2)OC1(C)C>C1CCOC1.O=C(O)O.[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][c:17](-[c:18]3[n:19][c:20](-[c:21]4[n:22][c:23]5[c:24]([cH:25][cH:26][n:27][cH:28]5)[o:29]4)[c:30]([NH2:31])[n:32][cH:33]3)[cH:34][cH:35]2)[CH2:36][CH2:37]1\"}",
"reactionStep": {
"id": "sa_a122c11534f15a35f54503dd",
"reactionHash": "41afe2e042668919eca67ef250a8a5d79aea4959114e032332241cbde6e5a99d"
},
"children": [
{
"id": "5256",
"routeId": "sa_7d2058340ec2a52c7b8d4995",
"moleculeId": "sa_b3cfa42c1f31f426aec35f39",
"parentId": "5255",
"isLeaf": false,
"molecule": {
"id": "sa_b3cfa42c1f31f426aec35f39",
"inchikey": "KEWHGEISZUSIPZ-UHFFFAOYSA-N",
"smiles": "Nc1ncc(Br)nc1-c1nc2cnccc2o1"
},
"smiles": "Nc1ncc(Br)nc1-c1nc2cnccc2o1",
"reactionStepId": "sa_e17b6408669e39fcadb4999f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110118275A1;0131;1056679\",\"rsmi\":\"O=C1CCC(=O)N1[Br:6].[NH2:1][c:2]1[n:3][cH:4][cH:5][n:7][c:8]1-[c:9]1[n:10][c:11]2[c:12]([cH:13][cH:14][n:15][cH:16]2)[o:17]1>CC(=O)O.O>[NH2:1][c:2]1[n:3][cH:4][c:5]([Br:6])[n:7][c:8]1-[c:9]1[n:10][c:11]2[c:12]([cH:13][cH:14][n:15][cH:16]2)[o:17]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:6].[NH2:1][c:2]1[n:3][cH:4][cH:5][n:7][c:8]1-[c:9]1[n:10][c:11]2[c:12]([cH:13][cH:14][n:15][cH:16]2)[o:17]1>CC(=O)O.O>[NH2:1][c:2]1[n:3][cH:4][c:5]([Br:6])[n:7][c:8]1-[c:9]1[n:10][c:11]2[c:12]([cH:13][cH:14][n:15][cH:16]2)[o:17]1\"}",
"reactionStep": {
"id": "sa_e17b6408669e39fcadb4999f",
"reactionHash": "4638282ebdc96a8aec36c09c5b2e58eeef9364628c4a68ae429d48d2b92c201e"
},
"children": [
{
"id": "5257",
"routeId": "sa_7d2058340ec2a52c7b8d4995",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "5256",
"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": "5258",
"routeId": "sa_7d2058340ec2a52c7b8d4995",
"moleculeId": "sa_8ae8dd7d692544a8c49dcdaf",
"parentId": "5256",
"isLeaf": false,
"molecule": {
"id": "sa_8ae8dd7d692544a8c49dcdaf",
"inchikey": "WOOWUTRDTJSUSF-UHFFFAOYSA-N",
"smiles": "Nc1nccnc1-c1nc2cnccc2o1"
},
"smiles": "Nc1nccnc1-c1nc2cnccc2o1",
"reactionStepId": "sa_6a59bcfdd88f4ae109b44a27",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110118275A1;0126;1056678\",\"rsmi\":\"O=[C:8]([c:7]1[c:2]([NH2:1])[n:3][cH:4][cH:5][n:6]1)[NH:9][c:10]1[c:11]([OH:16])[cH:12][cH:13][n:14][cH:15]1>CCN(CC)CC.ClC(Cl)(Cl)C(Cl)(Cl)Cl.ClCCl.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[NH2:1][c:2]1[n:3][cH:4][cH:5][n:6][c:7]1-[c:8]1[n:9][c:10]2[c:11]([cH:12][cH:13][n:14][cH:15]2)[o:16]1\"},\"mapped_reaction_smiles\":\"O=[C:8]([c:7]1[c:2]([NH2:1])[n:3][cH:4][cH:5][n:6]1)[NH:9][c:10]1[c:11]([OH:16])[cH:12][cH:13][n:14][cH:15]1>CCN(CC)CC.ClC(Cl)(Cl)C(Cl)(Cl)Cl.ClCCl.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[NH2:1][c:2]1[n:3][cH:4][cH:5][n:6][c:7]1-[c:8]1[n:9][c:10]2[c:11]([cH:12][cH:13][n:14][cH:15]2)[o:16]1\"}",
"reactionStep": {
"id": "sa_6a59bcfdd88f4ae109b44a27",
"reactionHash": "815c261cbeda4adff8cb4dedf89fa2c5e11f144f5b91062d15fa398b54828461"
},
"children": [
{
"id": "5259",
"routeId": "sa_7d2058340ec2a52c7b8d4995",
"moleculeId": "sa_87f4aadae937051557ae26c1",
"parentId": "5258",
"isLeaf": false,
"molecule": {
"id": "sa_87f4aadae937051557ae26c1",
"inchikey": "IVKHYVZQYURFTR-UHFFFAOYSA-N",
"smiles": "Nc1nccnc1C(=O)Nc1cnccc1O"
},
"smiles": "Nc1nccnc1C(=O)Nc1cnccc1O",
"reactionStepId": "sa_e451dac140324acf0b0e851f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110118275A1;0121;1056677\",\"rsmi\":\"O[C:8]([c:7]1[c:2]([NH2:1])[n:3][cH:4][cH:5][n:6]1)=[O:9].[NH2:10][c:11]1[c:12]([OH:13])[cH:14][cH:15][n:16][cH:17]1>CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.F[B-](F)(F)F>[NH2:1][c:2]1[n:3][cH:4][cH:5][n:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[c:12]([OH:13])[cH:14][cH:15][n:16][cH:17]1\"},\"mapped_reaction_smiles\":\"O[C:8]([c:7]1[c:2]([NH2:1])[n:3][cH:4][cH:5][n:6]1)=[O:9].[NH2:10][c:11]1[c:12]([OH:13])[cH:14][cH:15][n:16][cH:17]1>CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.F[B-](F)(F)F>[NH2:1][c:2]1[n:3][cH:4][cH:5][n:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[c:12]([OH:13])[cH:14][cH:15][n:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_e451dac140324acf0b0e851f",
"reactionHash": "f7af0f6a6661969b51a93581733299bbd87c34f5144b2ad134d589af40983aec"
},
"children": [
{
"id": "5260",
"routeId": "sa_7d2058340ec2a52c7b8d4995",
"moleculeId": "sa_c8a0559f9976f0aeb456bb8d",
"parentId": "5259",
"isLeaf": true,
"molecule": {
"id": "sa_c8a0559f9976f0aeb456bb8d",
"inchikey": "OIIBRAGQGFLUFI-UHFFFAOYSA-N",
"smiles": "Nc1c[nH]ccc1=O"
},
"smiles": "Nc1cnccc1O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5261",
"routeId": "sa_7d2058340ec2a52c7b8d4995",
"moleculeId": "sa_be102b38f7c5e5bdc2ebc064",
"parentId": "5259",
"isLeaf": true,
"molecule": {
"id": "sa_be102b38f7c5e5bdc2ebc064",
"inchikey": "ZAGZIOYVEIDDJA-UHFFFAOYSA-N",
"smiles": "Nc1nccnc1C(=O)O"
},
"smiles": "Nc1nccnc1C(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "5262",
"routeId": "sa_7d2058340ec2a52c7b8d4995",
"moleculeId": "sa_ac6ef807638c821f386646f4",
"parentId": "5255",
"isLeaf": true,
"molecule": {
"id": "sa_ac6ef807638c821f386646f4",
"inchikey": "QPYOLSJFOCIOHK-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCN(C(=O)c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCN(C(=O)c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}