Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(=O)N1CCc2nc(N3CCC(Oc4ccc(F)cc4F)CC3)c(N[C@H]3CCOC3)nc2C1
InChiKey
HSWVJQBEXRKOBZ-KRWDZBQOSA-N
Route Signature
de38110d8b95f32778ac6d6e399130be81ea19f4d56b371059c4465b1acaada4
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_1c88a83b28e33135d4d861a2",
"signature": "de38110d8b95f32778ac6d6e399130be81ea19f4d56b371059c4465b1acaada4",
"contentHash": "d376e193ea052f7aaf0956468d85bd3564960fa73ee91a9790f1e663559721a2",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_a76319c52de1dbb0896bd5ce",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00985",
"moleculeId": "sa_447eb349e2e62eebaad92e8d",
"smiles": "CC(=O)N1CCc2nc(N3CCC(Oc4ccc(F)cc4F)CC3)c(N[C@H]3CCOC3)nc2C1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_447eb349e2e62eebaad92e8d",
"inchikey": "HSWVJQBEXRKOBZ-KRWDZBQOSA-N",
"smiles": "CC(=O)N1CCc2nc(N3CCC(Oc4ccc(F)cc4F)CC3)c(N[C@H]3CCOC3)nc2C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "5203",
"routeId": "sa_1c88a83b28e33135d4d861a2",
"moleculeId": "sa_447eb349e2e62eebaad92e8d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_447eb349e2e62eebaad92e8d",
"inchikey": "HSWVJQBEXRKOBZ-KRWDZBQOSA-N",
"smiles": "CC(=O)N1CCc2nc(N3CCC(Oc4ccc(F)cc4F)CC3)c(N[C@H]3CCOC3)nc2C1"
},
"smiles": "CC(=O)N1CCc2nc(N3CCC(Oc4ccc(F)cc4F)CC3)c(N[C@H]3CCOC3)nc2C1",
"reactionStepId": "sa_35036f58e15a653b4612895c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160031881A1;0614;1832840\",\"rsmi\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[n:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([N:10]3[CH2:11][CH2:12][CH:13]([O:14][c:15]4[c:16]([F:17])[cH:18][c:19]([F:20])[cH:21][cH:22]4)[CH2:23][CH2:24]3)[c:25]([NH:26][C@H:27]3[CH2:28][CH2:29][O:30][CH2:31]3)[n:32][c:33]2[cH:34]1>C1COCCO1.CC(C)=O.[Pd]>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[n:8][c:9]([N:10]3[CH2:11][CH2:12][CH:13]([O:14][c:15]4[c:16]([F:17])[cH:18][c:19]([F:20])[cH:21][cH:22]4)[CH2:23][CH2:24]3)[c:25]([NH:26][C@H:27]3[CH2:28][CH2:29][O:30][CH2:31]3)[n:32][c:33]2[CH2:34]1\"},\"mapped_reaction_smiles\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[n:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([N:10]3[CH2:11][CH2:12][CH:13]([O:14][c:15]4[c:16]([F:17])[cH:18][c:19]([F:20])[cH:21][cH:22]4)[CH2:23][CH2:24]3)[c:25]([NH:26][C@H:27]3[CH2:28][CH2:29][O:30][CH2:31]3)[n:32][c:33]2[cH:34]1>C1COCCO1.CC(C)=O.[Pd]>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[n:8][c:9]([N:10]3[CH2:11][CH2:12][CH:13]([O:14][c:15]4[c:16]([F:17])[cH:18][c:19]([F:20])[cH:21][cH:22]4)[CH2:23][CH2:24]3)[c:25]([NH:26][C@H:27]3[CH2:28][CH2:29][O:30][CH2:31]3)[n:32][c:33]2[CH2:34]1\"}",
"reactionStep": {
"id": "sa_35036f58e15a653b4612895c",
"reactionHash": "9b2733c68c59e940649c49a7c083df549051e1171d25ec33b9586885c7fb957f"
},
"children": [
{
"id": "5204",
"routeId": "sa_1c88a83b28e33135d4d861a2",
"moleculeId": "sa_21c016ef0f372016aa002734",
"parentId": "5203",
"isLeaf": false,
"molecule": {
"id": "sa_21c016ef0f372016aa002734",
"inchikey": "KGXNIUAUXAFNFJ-HNNXBMFYSA-N",
"smiles": "Fc1ccc(OC2CCN(c3nc4ccncc4nc3N[C@H]3CCOC3)CC2)c(F)c1"
},
"smiles": "Fc1ccc(OC2CCN(c3nc4ccncc4nc3N[C@H]3CCOC3)CC2)c(F)c1",
"reactionStepId": "sa_c6b1ab8ba8634e3824aea28c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160031881A1;0220;1832663\",\"rsmi\":\"Cl[c:13]1[c:12]([N:11]2[CH2:10][CH2:9][CH:8]([O:7][c:6]3[c:4]([F:5])[cH:3][c:2]([F:1])[cH:31][cH:30]3)[CH2:29][CH2:28]2)[n:27][c:26]2[c:21]([n:20]1)[cH:22][n:23][cH:24][cH:25]2.[NH2:14][C@H:15]1[CH2:16][CH2:17][O:18][CH2:19]1>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl>[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([c:12]3[c:13]([NH:14][C@H:15]4[CH2:16][CH2:17][O:18][CH2:19]4)[n:20][c:21]4[cH:22][n:23][cH:24][cH:25][c:26]4[n:27]3)[CH2:28][CH2:29]2)[cH:30][cH:31]1\"},\"mapped_reaction_smiles\":\"Cl[c:13]1[c:12]([N:11]2[CH2:10][CH2:9][CH:8]([O:7][c:6]3[c:4]([F:5])[cH:3][c:2]([F:1])[cH:31][cH:30]3)[CH2:29][CH2:28]2)[n:27][c:26]2[c:21]([n:20]1)[cH:22][n:23][cH:24][cH:25]2.[NH2:14][C@H:15]1[CH2:16][CH2:17][O:18][CH2:19]1>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl>[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([c:12]3[c:13]([NH:14][C@H:15]4[CH2:16][CH2:17][O:18][CH2:19]4)[n:20][c:21]4[cH:22][n:23][cH:24][cH:25][c:26]4[n:27]3)[CH2:28][CH2:29]2)[cH:30][cH:31]1\"}",
"reactionStep": {
"id": "sa_c6b1ab8ba8634e3824aea28c",
"reactionHash": "d43255e16719cbc09896b7ef9403c03a6402d57be1526fe7253969361bc0cc8d"
},
"children": [
{
"id": "5205",
"routeId": "sa_1c88a83b28e33135d4d861a2",
"moleculeId": "sa_ccfe6e49033ae3958a9525ff",
"parentId": "5204",
"isLeaf": true,
"molecule": {
"id": "sa_ccfe6e49033ae3958a9525ff",
"inchikey": "MIPHRQMEIYLZFZ-BYPYZUCNSA-N",
"smiles": "N[C@H]1CCOC1"
},
"smiles": "N[C@H]1CCOC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5206",
"routeId": "sa_1c88a83b28e33135d4d861a2",
"moleculeId": "sa_251842cb4f77c31fabfc8dc0",
"parentId": "5204",
"isLeaf": false,
"molecule": {
"id": "sa_251842cb4f77c31fabfc8dc0",
"inchikey": "WPLUODBBIILLQG-UHFFFAOYSA-N",
"smiles": "Fc1ccc(OC2CCN(c3nc4ccncc4nc3Cl)CC2)c(F)c1"
},
"smiles": "Fc1ccc(OC2CCN(c3nc4ccncc4nc3Cl)CC2)c(F)c1",
"reactionStepId": "sa_e82e81da7f74527ebb953491",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160031881A1;0205;1832655\",\"rsmi\":\"Cl[c:12]1[c:13]([Cl:14])[n:15][c:16]2[cH:17][n:18][cH:19][cH:20][c:21]2[n:22]1.[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]([O:7][CH:8]2[CH2:9][CH2:10][NH:11][CH2:23][CH2:24]2)[cH:25][cH:26]1>CCN(C(C)C)C(C)C.Cl.ClCCl>[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([c:12]3[c:13]([Cl:14])[n:15][c:16]4[cH:17][n:18][cH:19][cH:20][c:21]4[n:22]3)[CH2:23][CH2:24]2)[cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"Cl[c:12]1[c:13]([Cl:14])[n:15][c:16]2[cH:17][n:18][cH:19][cH:20][c:21]2[n:22]1.[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]([O:7][CH:8]2[CH2:9][CH2:10][NH:11][CH2:23][CH2:24]2)[cH:25][cH:26]1>CCN(C(C)C)C(C)C.Cl.ClCCl>[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([c:12]3[c:13]([Cl:14])[n:15][c:16]4[cH:17][n:18][cH:19][cH:20][c:21]4[n:22]3)[CH2:23][CH2:24]2)[cH:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_e82e81da7f74527ebb953491",
"reactionHash": "f90b6c44d271067fc42c1ed29eb225e9d37c74a58f51a25a0cc0dbb2e08f737e"
},
"children": [
{
"id": "5207",
"routeId": "sa_1c88a83b28e33135d4d861a2",
"moleculeId": "sa_b723fd586baa71779c9e70cc",
"parentId": "5206",
"isLeaf": true,
"molecule": {
"id": "sa_b723fd586baa71779c9e70cc",
"inchikey": "GZTHKSLJDQQAGP-UHFFFAOYSA-N",
"smiles": "Clc1nc2ccncc2nc1Cl"
},
"smiles": "Clc1nc2ccncc2nc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5208",
"routeId": "sa_1c88a83b28e33135d4d861a2",
"moleculeId": "sa_1decb9cdd5727dd078e07a21",
"parentId": "5206",
"isLeaf": false,
"molecule": {
"id": "sa_1decb9cdd5727dd078e07a21",
"inchikey": "LJTKODIQFDAGSL-UHFFFAOYSA-N",
"smiles": "Fc1ccc(OC2CCNCC2)c(F)c1"
},
"smiles": "Fc1ccc(OC2CCNCC2)c(F)c1",
"reactionStepId": "sa_0fa0d3c4b1f8c38fe947038e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160031881A1;0179;1832633\",\"rsmi\":\"CC(C)(C)OC(=O)[N:11]1[CH2:10][CH2:9][CH:8]([O:7][c:6]2[c:4]([F:5])[cH:3][c:2]([F:1])[cH:15][cH:14]2)[CH2:13][CH2:12]1>CCOC(C)=O.Cl>[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]([O:7][CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:11]1[CH2:10][CH2:9][CH:8]([O:7][c:6]2[c:4]([F:5])[cH:3][c:2]([F:1])[cH:15][cH:14]2)[CH2:13][CH2:12]1>CCOC(C)=O.Cl>[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]([O:7][CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[cH:14][cH:15]1\"}",
"reactionStep": {
"id": "sa_0fa0d3c4b1f8c38fe947038e",
"reactionHash": "379d1e11b076b7ae73ae6a2083fa99540c404043392231fe8aafc0867d9c619d"
},
"children": [
{
"id": "5209",
"routeId": "sa_1c88a83b28e33135d4d861a2",
"moleculeId": "sa_b13b0949c07603ea36355202",
"parentId": "5208",
"isLeaf": false,
"molecule": {
"id": "sa_b13b0949c07603ea36355202",
"inchikey": "CUURPZRWNPWPKM-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(Oc2ccc(F)cc2F)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(Oc2ccc(F)cc2F)CC1",
"reactionStepId": "sa_f7b7f3094bded2d6990fd358",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160031881A1;0178;1832632\",\"rsmi\":\"O[c:13]1[c:14]([F:15])[cH:16][c:17]([F:18])[cH:19][cH:20]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([OH:12])[CH2:21][CH2:22]1>C1CCOC1.CCOC(=O)/N=N/C(=O)OCC.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[c:14]([F:15])[cH:16][c:17]([F:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1\"},\"mapped_reaction_smiles\":\"O[c:13]1[c:14]([F:15])[cH:16][c:17]([F:18])[cH:19][cH:20]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([OH:12])[CH2:21][CH2:22]1>C1CCOC1.CCOC(=O)/N=N/C(=O)OCC.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[c:14]([F:15])[cH:16][c:17]([F:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1\"}",
"reactionStep": {
"id": "sa_f7b7f3094bded2d6990fd358",
"reactionHash": "0f95a7471763162729b194c8ac3597b0b7d9dd26cb2819b29a26e9d131d328b2"
},
"children": [
{
"id": "5210",
"routeId": "sa_1c88a83b28e33135d4d861a2",
"moleculeId": "sa_efc5aa97f1feb80bd5e1e2a5",
"parentId": "5209",
"isLeaf": true,
"molecule": {
"id": "sa_efc5aa97f1feb80bd5e1e2a5",
"inchikey": "NVWVWEWVLBKPSM-UHFFFAOYSA-N",
"smiles": "Oc1ccc(F)cc1F"
},
"smiles": "Oc1ccc(F)cc1F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5211",
"routeId": "sa_1c88a83b28e33135d4d861a2",
"moleculeId": "sa_08f912c37482cb09c1da49c0",
"parentId": "5209",
"isLeaf": true,
"molecule": {
"id": "sa_08f912c37482cb09c1da49c0",
"inchikey": "PWQLFIKTGRINFF-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(O)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(O)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
},
{
"id": "5212",
"routeId": "sa_1c88a83b28e33135d4d861a2",
"moleculeId": "sa_a7893fcf81826693d9b4bed4",
"parentId": "5203",
"isLeaf": true,
"molecule": {
"id": "sa_a7893fcf81826693d9b4bed4",
"inchikey": "WFDIJRYMOXRFFG-UHFFFAOYSA-N",
"smiles": "CC(=O)OC(C)=O"
},
"smiles": "CC(=O)OC(C)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}