Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCc1cnc(N2CCC(c3nc4cc(-c5ccc(S(C)(=O)=O)cc5F)ccc4[nH]3)CC2)nc1
InChiKey
VPLFACVZKYCYRJ-UHFFFAOYSA-N
Route Signature
fb6b5a8f3cfcd0a4a1c24f91bd31b2a7d0758d5be24ff95e1c44de974fc6aba2
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_f89cfc9cb5c6e960b3e4777b",
"signature": "fb6b5a8f3cfcd0a4a1c24f91bd31b2a7d0758d5be24ff95e1c44de974fc6aba2",
"contentHash": "eb9bbdc831e73e4a1294f02fd8440dea2c75239cb91d6cda7d11ef0c083e7163",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_4ed5c95ab40a5f3a3f3524c6",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-05386",
"moleculeId": "sa_326ce786b7d8ccc8eb6745a1",
"smiles": "CCc1cnc(N2CCC(c3nc4cc(-c5ccc(S(C)(=O)=O)cc5F)ccc4[nH]3)CC2)nc1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_326ce786b7d8ccc8eb6745a1",
"inchikey": "VPLFACVZKYCYRJ-UHFFFAOYSA-N",
"smiles": "CCc1cnc(N2CCC(c3nc4cc(-c5ccc(S(C)(=O)=O)cc5F)ccc4[nH]3)CC2)nc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "2764",
"routeId": "sa_f89cfc9cb5c6e960b3e4777b",
"moleculeId": "sa_326ce786b7d8ccc8eb6745a1",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_326ce786b7d8ccc8eb6745a1",
"inchikey": "VPLFACVZKYCYRJ-UHFFFAOYSA-N",
"smiles": "CCc1cnc(N2CCC(c3nc4cc(-c5ccc(S(C)(=O)=O)cc5F)ccc4[nH]3)CC2)nc1"
},
"smiles": "CCc1cnc(N2CCC(c3nc4cc(-c5ccc(S(C)(=O)=O)cc5F)ccc4[nH]3)CC2)nc1",
"reactionStepId": "sa_91e5e7dac888946557b4a6d6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130045986A1;0356;1336155\",\"rsmi\":\"Br[c:17]1[cH:16][cH:15][c:14]2[c:13]([n:12][c:11]([CH:10]3[CH2:9][CH2:8][N:7]([c:6]4[n:5][cH:4][c:3]([CH2:2][CH3:1])[cH:34][n:33]4)[CH2:32][CH2:31]3)[nH:30]2)[cH:29]1.CC1(C)OB([c:18]2[c:19]([F:20])[cH:21][c:22]([S:23]([CH3:24])(=[O:25])=[O:26])[cH:27][cH:28]2)OC1(C)C>>[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]2[CH2:8][CH2:9][CH:10]([c:11]3[n:12][c:13]4[c:14]([cH:15][cH:16][c:17](-[c:18]5[c:19]([F:20])[cH:21][c:22]([S:23]([CH3:24])(=[O:25])=[O:26])[cH:27][cH:28]5)[cH:29]4)[nH:30]3)[CH2:31][CH2:32]2)[n:33][cH:34]1\"},\"mapped_reaction_smiles\":\"Br[c:17]1[cH:16][cH:15][c:14]2[c:13]([n:12][c:11]([CH:10]3[CH2:9][CH2:8][N:7]([c:6]4[n:5][cH:4][c:3]([CH2:2][CH3:1])[cH:34][n:33]4)[CH2:32][CH2:31]3)[nH:30]2)[cH:29]1.CC1(C)OB([c:18]2[c:19]([F:20])[cH:21][c:22]([S:23]([CH3:24])(=[O:25])=[O:26])[cH:27][cH:28]2)OC1(C)C>>[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]2[CH2:8][CH2:9][CH:10]([c:11]3[n:12][c:13]4[c:14]([cH:15][cH:16][c:17](-[c:18]5[c:19]([F:20])[cH:21][c:22]([S:23]([CH3:24])(=[O:25])=[O:26])[cH:27][cH:28]5)[cH:29]4)[nH:30]3)[CH2:31][CH2:32]2)[n:33][cH:34]1\"}",
"reactionStep": {
"id": "sa_91e5e7dac888946557b4a6d6",
"reactionHash": "78e044f2bbeaf1add43e0e1495c6eed28904200659a5b987df54dba2b15365fa"
},
"children": [
{
"id": "2765",
"routeId": "sa_f89cfc9cb5c6e960b3e4777b",
"moleculeId": "sa_5af3fa95bd1c81a1e770eaab",
"parentId": "2764",
"isLeaf": false,
"molecule": {
"id": "sa_5af3fa95bd1c81a1e770eaab",
"inchikey": "NCPFIZKMEKKGMJ-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2ccc(S(C)(=O)=O)cc2F)OC1(C)C"
},
"smiles": "CC1(C)OB(c2ccc(S(C)(=O)=O)cc2F)OC1(C)C",
"reactionStepId": "sa_caab9dd8da9472b522283e27",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130045986A1;0293;1336097\",\"rsmi\":\"Br[c:6]1[c:7]([F:8])[cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:16]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:18]([CH3:19])([CH3:20])[O:17]2)OC1(C)C>C1COCCO1.CC(=O)O.CCOC(C)=O.ClCCl.O.O.[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]([F:8])[cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:16]2)[O:17][C:18]1([CH3:19])[CH3:20]\"},\"mapped_reaction_smiles\":\"Br[c:6]1[c:7]([F:8])[cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:16]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:18]([CH3:19])([CH3:20])[O:17]2)OC1(C)C>C1COCCO1.CC(=O)O.CCOC(C)=O.ClCCl.O.O.[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]([F:8])[cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:16]2)[O:17][C:18]1([CH3:19])[CH3:20]\"}",
"reactionStep": {
"id": "sa_caab9dd8da9472b522283e27",
"reactionHash": "3bd197bc1df8fb62d925c12eea585412b00b0086cedcfc44c2b4537c79eab8f8"
},
"children": [
{
"id": "2766",
"routeId": "sa_f89cfc9cb5c6e960b3e4777b",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "2765",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2767",
"routeId": "sa_f89cfc9cb5c6e960b3e4777b",
"moleculeId": "sa_7be70565aec1bb402c5034cc",
"parentId": "2765",
"isLeaf": true,
"molecule": {
"id": "sa_7be70565aec1bb402c5034cc",
"inchikey": "QALKAUDOPSIGEI-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)c1ccc(Br)c(F)c1"
},
"smiles": "CS(=O)(=O)c1ccc(Br)c(F)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "2768",
"routeId": "sa_f89cfc9cb5c6e960b3e4777b",
"moleculeId": "sa_0250f20f90c80553736e47b3",
"parentId": "2764",
"isLeaf": false,
"molecule": {
"id": "sa_0250f20f90c80553736e47b3",
"inchikey": "ZMBLWTKWTKLJSS-UHFFFAOYSA-N",
"smiles": "CCc1cnc(N2CCC(c3nc4cc(Br)ccc4[nH]3)CC2)nc1"
},
"smiles": "CCc1cnc(N2CCC(c3nc4cc(Br)ccc4[nH]3)CC2)nc1",
"reactionStepId": "sa_4e1990b45d3044200e4beca2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130045986A1;0292;1336096\",\"rsmi\":\"Cl[c:6]1[n:5][cH:4][c:3]([CH2:2][CH3:1])[cH:24][n:23]1.[NH:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][c:13]3[c:14]([cH:15][cH:16][c:17]([Br:18])[cH:19]3)[nH:20]2)[CH2:21][CH2:22]1>CC(C)O.CCN(C(C)C)C(C)C>[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]2[CH2:8][CH2:9][CH:10]([c:11]3[n:12][c:13]4[c:14]([cH:15][cH:16][c:17]([Br:18])[cH:19]4)[nH:20]3)[CH2:21][CH2:22]2)[n:23][cH:24]1\"},\"mapped_reaction_smiles\":\"Cl[c:6]1[n:5][cH:4][c:3]([CH2:2][CH3:1])[cH:24][n:23]1.[NH:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][c:13]3[c:14]([cH:15][cH:16][c:17]([Br:18])[cH:19]3)[nH:20]2)[CH2:21][CH2:22]1>CC(C)O.CCN(C(C)C)C(C)C>[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]2[CH2:8][CH2:9][CH:10]([c:11]3[n:12][c:13]4[c:14]([cH:15][cH:16][c:17]([Br:18])[cH:19]4)[nH:20]3)[CH2:21][CH2:22]2)[n:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_4e1990b45d3044200e4beca2",
"reactionHash": "389a385cbba8b4c882725f0f44b5fb7f89a78b03603ee86ba18aaa813d997960"
},
"children": [
{
"id": "2769",
"routeId": "sa_f89cfc9cb5c6e960b3e4777b",
"moleculeId": "sa_b7bf82c61690ec3a9ded2925",
"parentId": "2768",
"isLeaf": true,
"molecule": {
"id": "sa_b7bf82c61690ec3a9ded2925",
"inchikey": "BGLLZQRUXJGTAD-UHFFFAOYSA-N",
"smiles": "CCc1cnc(Cl)nc1"
},
"smiles": "CCc1cnc(Cl)nc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2770",
"routeId": "sa_f89cfc9cb5c6e960b3e4777b",
"moleculeId": "sa_c26c5d6f32a78d54b424f701",
"parentId": "2768",
"isLeaf": false,
"molecule": {
"id": "sa_c26c5d6f32a78d54b424f701",
"inchikey": "JGTQZDUEIGZJCX-UHFFFAOYSA-N",
"smiles": "Brc1ccc2[nH]c(C3CCNCC3)nc2c1"
},
"smiles": "Brc1ccc2[nH]c(C3CCNCC3)nc2c1",
"reactionStepId": "sa_b5772fc70c826ea12fcb928e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130045986A1;0291;1336095\",\"rsmi\":\"O=[C:9](O)[CH:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1.[Br:1][c:2]1[cH:3][c:4]([NH2:16])[c:5]([NH2:8])[cH:6][cH:7]1>O.[Na+].O>[Br:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[nH:8][c:9]([CH:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1)[n:16]2\"},\"mapped_reaction_smiles\":\"O=[C:9](O)[CH:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1.[Br:1][c:2]1[cH:3][c:4]([NH2:16])[c:5]([NH2:8])[cH:6][cH:7]1>O.[Na+].O>[Br:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[nH:8][c:9]([CH:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1)[n:16]2\"}",
"reactionStep": {
"id": "sa_b5772fc70c826ea12fcb928e",
"reactionHash": "d706ea45d3b00eb83177b2341adced153d8544c88ebe42bebccde4d382a9cdf1"
},
"children": [
{
"id": "2771",
"routeId": "sa_f89cfc9cb5c6e960b3e4777b",
"moleculeId": "sa_a5862e3e657d063c6a19e866",
"parentId": "2770",
"isLeaf": true,
"molecule": {
"id": "sa_a5862e3e657d063c6a19e866",
"inchikey": "SRJOCJYGOFTFLH-UHFFFAOYSA-N",
"smiles": "O=C(O)C1CCNCC1"
},
"smiles": "O=C(O)C1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2772",
"routeId": "sa_f89cfc9cb5c6e960b3e4777b",
"moleculeId": "sa_d0e24a3ca440aba134df6f8c",
"parentId": "2770",
"isLeaf": true,
"molecule": {
"id": "sa_d0e24a3ca440aba134df6f8c",
"inchikey": "WIHHVKUARKTSBU-UHFFFAOYSA-N",
"smiles": "Nc1ccc(Br)cc1N"
},
"smiles": "Nc1ccc(Br)cc1N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}