Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(c1ccc(F)cc1)C1CCN(CC(=O)N(Cc2ccc(F)cc2)Cc2nc3c(c(=O)[nH]2)COCC3)CC1
InChiKey
GNEZFZTYMMBMNW-UHFFFAOYSA-N
Route Signature
f1b2d46c26592aca4d4808f7471cc6f5913228cffe7a3bfb1f5b3bb6c79496cc
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_949cc49a923ba2f4901ce350",
"signature": "f1b2d46c26592aca4d4808f7471cc6f5913228cffe7a3bfb1f5b3bb6c79496cc",
"contentHash": "6c83b7208146977f1137c56aa7d69468c0eed3a875aedc4fccbd76abf62a80e1",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_938b1d59ad61537fe10aa532",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01265",
"moleculeId": "sa_27d5c302c7da98658b071bfb",
"smiles": "O=C(c1ccc(F)cc1)C1CCN(CC(=O)N(Cc2ccc(F)cc2)Cc2nc3c(c(=O)[nH]2)COCC3)CC1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_27d5c302c7da98658b071bfb",
"inchikey": "GNEZFZTYMMBMNW-UHFFFAOYSA-N",
"smiles": "O=C(c1ccc(F)cc1)C1CCN(CC(=O)N(Cc2ccc(F)cc2)Cc2nc3c(c(=O)[nH]2)COCC3)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10044",
"routeId": "sa_949cc49a923ba2f4901ce350",
"moleculeId": "sa_27d5c302c7da98658b071bfb",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_27d5c302c7da98658b071bfb",
"inchikey": "GNEZFZTYMMBMNW-UHFFFAOYSA-N",
"smiles": "O=C(c1ccc(F)cc1)C1CCN(CC(=O)N(Cc2ccc(F)cc2)Cc2nc3c(c(=O)[nH]2)COCC3)CC1"
},
"smiles": "O=C(c1ccc(F)cc1)C1CCN(CC(=O)N(Cc2ccc(F)cc2)Cc2nc3c(c(=O)[nH]2)COCC3)CC1",
"reactionStepId": "sa_1d69d3fec5b15cb36dc160c2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09181266B2;0618;1693451\",\"rsmi\":\"O[C:15](=[O:16])[CH2:17][N:18]1[CH2:19][CH2:20][CH:21]([C:22](=[O:23])[c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[CH2:31][CH2:32]1.[O:1]=[c:2]1[nH:3][c:4]([CH2:5][NH:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:33][c:34]2[c:35]1[CH2:36][O:37][CH2:38][CH2:39]2>>[O:1]=[c:2]1[nH:3][c:4]([CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[C:15](=[O:16])[CH2:17][N:18]2[CH2:19][CH2:20][CH:21]([C:22](=[O:23])[c:24]3[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]3)[CH2:31][CH2:32]2)[n:33][c:34]2[c:35]1[CH2:36][O:37][CH2:38][CH2:39]2\"},\"mapped_reaction_smiles\":\"O[C:15](=[O:16])[CH2:17][N:18]1[CH2:19][CH2:20][CH:21]([C:22](=[O:23])[c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[CH2:31][CH2:32]1.[O:1]=[c:2]1[nH:3][c:4]([CH2:5][NH:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:33][c:34]2[c:35]1[CH2:36][O:37][CH2:38][CH2:39]2>>[O:1]=[c:2]1[nH:3][c:4]([CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[C:15](=[O:16])[CH2:17][N:18]2[CH2:19][CH2:20][CH:21]([C:22](=[O:23])[c:24]3[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]3)[CH2:31][CH2:32]2)[n:33][c:34]2[c:35]1[CH2:36][O:37][CH2:38][CH2:39]2\"}",
"reactionStep": {
"id": "sa_1d69d3fec5b15cb36dc160c2",
"reactionHash": "e2e18f0b7382e884de94651f4219a1f6410af6fcf79ab53cbd12d9e781fa501c"
},
"children": [
{
"id": "10045",
"routeId": "sa_949cc49a923ba2f4901ce350",
"moleculeId": "sa_288c1c2deacdbcf0b07ae9dd",
"parentId": "10044",
"isLeaf": false,
"molecule": {
"id": "sa_288c1c2deacdbcf0b07ae9dd",
"inchikey": "DWYCQVSHMHQPSR-UHFFFAOYSA-N",
"smiles": "O=C(O)CN1CCC(C(=O)c2ccc(F)cc2)CC1"
},
"smiles": "O=C(O)CN1CCC(C(=O)c2ccc(F)cc2)CC1",
"reactionStepId": "sa_53f2d9ed1fff255a477f4b29",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09181266B2;0448;1693389\",\"rsmi\":\"CC[O:3][C:2](=[O:1])[CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1>CCO.Cl.O.[Na+].O>[O:1]=[C:2]([OH:3])[CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1\"},\"mapped_reaction_smiles\":\"CC[O:3][C:2](=[O:1])[CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1>CCO.Cl.O.[Na+].O>[O:1]=[C:2]([OH:3])[CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1\"}",
"reactionStep": {
"id": "sa_53f2d9ed1fff255a477f4b29",
"reactionHash": "a6d5a669129b976a5dd9c4a6b680f21521fe66b36abdf877c9d94326bcc4bb86"
},
"children": [
{
"id": "10046",
"routeId": "sa_949cc49a923ba2f4901ce350",
"moleculeId": "sa_c93b1501bc6de5cacc0f4b44",
"parentId": "10045",
"isLeaf": false,
"molecule": {
"id": "sa_c93b1501bc6de5cacc0f4b44",
"inchikey": "DJEAJNZQTSBMFP-UHFFFAOYSA-N",
"smiles": "CCOC(=O)CN1CCC(C(=O)c2ccc(F)cc2)CC1"
},
"smiles": "CCOC(=O)CN1CCC(C(=O)c2ccc(F)cc2)CC1",
"reactionStepId": "sa_80264325da5dd303275432e3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09181266B2;0446;1693388\",\"rsmi\":\"Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:7]1[CH2:8][CH2:9][CH:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[CH2:20][CH2:21]1>CC#N.CCN(CC)CC.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[CH2:20][CH2:21]1\"},\"mapped_reaction_smiles\":\"Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:7]1[CH2:8][CH2:9][CH:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[CH2:20][CH2:21]1>CC#N.CCN(CC)CC.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[CH2:20][CH2:21]1\"}",
"reactionStep": {
"id": "sa_80264325da5dd303275432e3",
"reactionHash": "6c7d04086641565728b60ec8aadfa03b5aeadeb134b5bd226cf37df976caa18b"
},
"children": [
{
"id": "10047",
"routeId": "sa_949cc49a923ba2f4901ce350",
"moleculeId": "sa_f34483c87e12299c7614b41c",
"parentId": "10046",
"isLeaf": true,
"molecule": {
"id": "sa_f34483c87e12299c7614b41c",
"inchikey": "ABERUOJGWHYBJL-UHFFFAOYSA-N",
"smiles": "O=C(c1ccc(F)cc1)C1CCNCC1"
},
"smiles": "O=C(c1ccc(F)cc1)C1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10048",
"routeId": "sa_949cc49a923ba2f4901ce350",
"moleculeId": "sa_6170bddd2f4a4137325c4a17",
"parentId": "10046",
"isLeaf": true,
"molecule": {
"id": "sa_6170bddd2f4a4137325c4a17",
"inchikey": "PQJJJMRNHATNKG-UHFFFAOYSA-N",
"smiles": "CCOC(=O)CBr"
},
"smiles": "CCOC(=O)CBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "10049",
"routeId": "sa_949cc49a923ba2f4901ce350",
"moleculeId": "sa_1d5e886db797fb639c8b01de",
"parentId": "10044",
"isLeaf": false,
"molecule": {
"id": "sa_1d5e886db797fb639c8b01de",
"inchikey": "FGYANAUOMZIICJ-UHFFFAOYSA-N",
"smiles": "O=c1[nH]c(CNCc2ccc(F)cc2)nc2c1COCC2"
},
"smiles": "O=c1[nH]c(CNCc2ccc(F)cc2)nc2c1COCC2",
"reactionStepId": "sa_96327ffb9ad869294169dc0c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09181266B2;0304;1693353\",\"rsmi\":\"Br[CH2:7][c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1.[O:1]=[c:2]1[nH:3][c:4]([CH2:5][NH2:6])[n:15][c:16]2[c:17]1[CH2:18][O:19][CH2:20][CH2:21]2>CCCCCC.CCO.CO.ClCCl>[O:1]=[c:2]1[nH:3][c:4]([CH2:5][NH:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15][c:16]2[c:17]1[CH2:18][O:19][CH2:20][CH2:21]2\"},\"mapped_reaction_smiles\":\"Br[CH2:7][c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1.[O:1]=[c:2]1[nH:3][c:4]([CH2:5][NH2:6])[n:15][c:16]2[c:17]1[CH2:18][O:19][CH2:20][CH2:21]2>CCCCCC.CCO.CO.ClCCl>[O:1]=[c:2]1[nH:3][c:4]([CH2:5][NH:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15][c:16]2[c:17]1[CH2:18][O:19][CH2:20][CH2:21]2\"}",
"reactionStep": {
"id": "sa_96327ffb9ad869294169dc0c",
"reactionHash": "51a57582947d45ae7f24f1d22c395100c978df677bcfdee65fd413ed8cbd94d3"
},
"children": [
{
"id": "10050",
"routeId": "sa_949cc49a923ba2f4901ce350",
"moleculeId": "sa_5f3ba7f73acc20e80a7a1bea",
"parentId": "10049",
"isLeaf": true,
"molecule": {
"id": "sa_5f3ba7f73acc20e80a7a1bea",
"inchikey": "NVNPLEPBDPJYRZ-UHFFFAOYSA-N",
"smiles": "Fc1ccc(CBr)cc1"
},
"smiles": "Fc1ccc(CBr)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10051",
"routeId": "sa_949cc49a923ba2f4901ce350",
"moleculeId": "sa_22b6725698823a62e026f09c",
"parentId": "10049",
"isLeaf": false,
"molecule": {
"id": "sa_22b6725698823a62e026f09c",
"inchikey": "OSCXEGLRKLOKBZ-UHFFFAOYSA-N",
"smiles": "NCc1nc2c(c(=O)[nH]1)COCC2"
},
"smiles": "NCc1nc2c(c(=O)[nH]1)COCC2",
"reactionStepId": "sa_cf8bce67b897cae07b792e06",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09181266B2;0282;1693346\",\"rsmi\":\"O=C(OCc1ccccc1)[NH:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([c:11](=[O:12])[nH:13]1)[CH2:7][O:8][CH2:9][CH2:10]2>CO.[Pd]>[NH2:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([c:11](=[O:12])[nH:13]1)[CH2:7][O:8][CH2:9][CH2:10]2\"},\"mapped_reaction_smiles\":\"O=C(OCc1ccccc1)[NH:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([c:11](=[O:12])[nH:13]1)[CH2:7][O:8][CH2:9][CH2:10]2>CO.[Pd]>[NH2:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([c:11](=[O:12])[nH:13]1)[CH2:7][O:8][CH2:9][CH2:10]2\"}",
"reactionStep": {
"id": "sa_cf8bce67b897cae07b792e06",
"reactionHash": "5d42ad4566007e5aa6b2b7993e66b8e09040eb5aa5129e249b885d412ad554b9"
},
"children": [
{
"id": "10052",
"routeId": "sa_949cc49a923ba2f4901ce350",
"moleculeId": "sa_36f74345a14d3ce85f30402c",
"parentId": "10051",
"isLeaf": false,
"molecule": {
"id": "sa_36f74345a14d3ce85f30402c",
"inchikey": "AXDGVKBSJFTEFS-UHFFFAOYSA-N",
"smiles": "O=C(NCc1nc2c(c(=O)[nH]1)COCC2)OCc1ccccc1"
},
"smiles": "O=C(NCc1nc2c(c(=O)[nH]1)COCC2)OCc1ccccc1",
"reactionStepId": "sa_9da0c186de124ac941a2a2d3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09181266B2;0279;1693344\",\"rsmi\":\"CO[C:13]([CH:8]1[C:7](=O)[CH2:12][CH2:11][O:10][CH2:9]1)=[O:14].[O:1]=[C:2]([NH:3][CH2:4][C:5](=[NH:6])[NH2:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>CCO.CCO.Cl.[Na+]>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:13](=[O:14])[nH:15]1)[CH2:9][O:10][CH2:11][CH2:12]2)[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"CO[C:13]([CH:8]1[C:7](=O)[CH2:12][CH2:11][O:10][CH2:9]1)=[O:14].[O:1]=[C:2]([NH:3][CH2:4][C:5](=[NH:6])[NH2:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>CCO.CCO.Cl.[Na+]>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:13](=[O:14])[nH:15]1)[CH2:9][O:10][CH2:11][CH2:12]2)[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1\"}",
"reactionStep": {
"id": "sa_9da0c186de124ac941a2a2d3",
"reactionHash": "c61536da44a0f0ae89eb55ec0224c40e07a8401d67d9402658aea2c6f3b1aa60"
},
"children": [
{
"id": "10053",
"routeId": "sa_949cc49a923ba2f4901ce350",
"moleculeId": "sa_9126902652678f790b200bd0",
"parentId": "10052",
"isLeaf": true,
"molecule": {
"id": "sa_9126902652678f790b200bd0",
"inchikey": "BNVPWJZNPNLYJI-UHFFFAOYSA-N",
"smiles": "N=C(N)CN=C(O)OCc1ccccc1"
},
"smiles": "N=C(N)CNC(=O)OCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10054",
"routeId": "sa_949cc49a923ba2f4901ce350",
"moleculeId": "sa_8e79d95cb06d3324e0224f67",
"parentId": "10052",
"isLeaf": true,
"molecule": {
"id": "sa_8e79d95cb06d3324e0224f67",
"inchikey": "SOWMVLQIMWETEK-UHFFFAOYSA-N",
"smiles": "COC(=O)C1COCCC1=O"
},
"smiles": "COC(=O)C1COCCC1=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}