Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)c1cc(O)cc(-c2nc(NC(=O)C3(c4ccc5c(c4)OC(F)(F)O5)CC3)ccc2C)c1
InChiKey
QAFUFXGXQHVOFN-UHFFFAOYSA-N
Route Signature
9f17c2e4e4d8f7f6c0bbd1ccd0121fdae276d9d5de28c4b6b2fdb81b3649ff2f
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_24adc0964d96eee075d7f0bc",
"signature": "9f17c2e4e4d8f7f6c0bbd1ccd0121fdae276d9d5de28c4b6b2fdb81b3649ff2f",
"contentHash": "7ea41dd30ed54bf6b94b8efe6e1141389a8f2ab14a432d2759e76886ef50b2e6",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_cd3b52f5e03a19f8d29279f6",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-03369",
"moleculeId": "sa_c9817f7dd9899eddda1f1e92",
"smiles": "COC(=O)c1cc(O)cc(-c2nc(NC(=O)C3(c4ccc5c(c4)OC(F)(F)O5)CC3)ccc2C)c1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_c9817f7dd9899eddda1f1e92",
"inchikey": "QAFUFXGXQHVOFN-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(O)cc(-c2nc(NC(=O)C3(c4ccc5c(c4)OC(F)(F)O5)CC3)ccc2C)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11017",
"routeId": "sa_24adc0964d96eee075d7f0bc",
"moleculeId": "sa_c9817f7dd9899eddda1f1e92",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c9817f7dd9899eddda1f1e92",
"inchikey": "QAFUFXGXQHVOFN-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(O)cc(-c2nc(NC(=O)C3(c4ccc5c(c4)OC(F)(F)O5)CC3)ccc2C)c1"
},
"smiles": "COC(=O)c1cc(O)cc(-c2nc(NC(=O)C3(c4ccc5c(c4)OC(F)(F)O5)CC3)ccc2C)c1",
"reactionStepId": "sa_0eb434c02b213b291b812875",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065500A1;0608;1660172\",\"rsmi\":\"CC1(C)OB([c:7]2[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:35][c:33]([OH:34])[cH:32]2)OC1(C)C.Cl[c:8]1[n:9][c:10]([NH:11][C:12](=[O:13])[C:14]2([c:15]3[cH:16][c:17]4[c:18]([cH:19][cH:20]3)[O:21][C:22]([F:23])([F:24])[O:25]4)[CH2:26][CH2:27]2)[cH:28][cH:29][c:30]1[CH3:31]>COCCOC.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[n:9][c:10]([NH:11][C:12](=[O:13])[C:14]3([c:15]4[cH:16][c:17]5[c:18]([cH:19][cH:20]4)[O:21][C:22]([F:23])([F:24])[O:25]5)[CH2:26][CH2:27]3)[cH:28][cH:29][c:30]2[CH3:31])[cH:32][c:33]([OH:34])[cH:35]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:7]2[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:35][c:33]([OH:34])[cH:32]2)OC1(C)C.Cl[c:8]1[n:9][c:10]([NH:11][C:12](=[O:13])[C:14]2([c:15]3[cH:16][c:17]4[c:18]([cH:19][cH:20]3)[O:21][C:22]([F:23])([F:24])[O:25]4)[CH2:26][CH2:27]2)[cH:28][cH:29][c:30]1[CH3:31]>COCCOC.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[n:9][c:10]([NH:11][C:12](=[O:13])[C:14]3([c:15]4[cH:16][c:17]5[c:18]([cH:19][cH:20]4)[O:21][C:22]([F:23])([F:24])[O:25]5)[CH2:26][CH2:27]3)[cH:28][cH:29][c:30]2[CH3:31])[cH:32][c:33]([OH:34])[cH:35]1\"}",
"reactionStep": {
"id": "sa_0eb434c02b213b291b812875",
"reactionHash": "999f6b6de181f72ea23b21d5807460413ce786437496aaf2118d428038ae3bda"
},
"children": [
{
"id": "11018",
"routeId": "sa_24adc0964d96eee075d7f0bc",
"moleculeId": "sa_eb8db51eefa8d380efed19c3",
"parentId": "11017",
"isLeaf": false,
"molecule": {
"id": "sa_eb8db51eefa8d380efed19c3",
"inchikey": "CXTSTJMTRHANCB-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(O)cc(B2OC(C)(C)C(C)(C)O2)c1"
},
"smiles": "COC(=O)c1cc(O)cc(B2OC(C)(C)C(C)(C)O2)c1",
"reactionStepId": "sa_945ecff3e3116e53c907bc3e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065500A1;0532;1660139\",\"rsmi\":\"Br[c:10]1[cH:9][c:7]([OH:8])[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:20]1.CC1(C)OB([B:11]2[O:12][C:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[O:19]2)OC1(C)C>CC(=O)O.CN(C)C=O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([OH:8])[cH:9][c:10]([B:11]2[O:12][C:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[O:19]2)[cH:20]1\"},\"mapped_reaction_smiles\":\"Br[c:10]1[cH:9][c:7]([OH:8])[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:20]1.CC1(C)OB([B:11]2[O:12][C:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[O:19]2)OC1(C)C>CC(=O)O.CN(C)C=O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([OH:8])[cH:9][c:10]([B:11]2[O:12][C:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[O:19]2)[cH:20]1\"}",
"reactionStep": {
"id": "sa_945ecff3e3116e53c907bc3e",
"reactionHash": "6b6ff4a1dc45b0a90aa09c9eb01a7b0bc183ed7737459b0f47be3280713458a6"
},
"children": [
{
"id": "11019",
"routeId": "sa_24adc0964d96eee075d7f0bc",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "11018",
"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": "11020",
"routeId": "sa_24adc0964d96eee075d7f0bc",
"moleculeId": "sa_a5d9f6677b7fb33e4482d75f",
"parentId": "11018",
"isLeaf": false,
"molecule": {
"id": "sa_a5d9f6677b7fb33e4482d75f",
"inchikey": "KRTBWIIGEJIUSA-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(O)cc(Br)c1"
},
"smiles": "COC(=O)c1cc(O)cc(Br)c1",
"reactionStepId": "sa_bc6a2492635581cb6b6c6982",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065500A1;0497;1660122\",\"rsmi\":\"O[C:3](=[O:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([OH:11])[cH:12]1.[CH3:1][OH:2]>Cc1ccc(S(=O)(=O)O)cc1.O=C(O)O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([OH:11])[cH:12]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([OH:11])[cH:12]1.[CH3:1][OH:2]>Cc1ccc(S(=O)(=O)O)cc1.O=C(O)O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([OH:11])[cH:12]1\"}",
"reactionStep": {
"id": "sa_bc6a2492635581cb6b6c6982",
"reactionHash": "54d14dc29a3cbd13a02914605dc77ec7851cdc3362587790f570bbaf1e576929"
},
"children": [
{
"id": "11021",
"routeId": "sa_24adc0964d96eee075d7f0bc",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "11020",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11022",
"routeId": "sa_24adc0964d96eee075d7f0bc",
"moleculeId": "sa_a9bf73330017ae6c9ce76aae",
"parentId": "11020",
"isLeaf": true,
"molecule": {
"id": "sa_a9bf73330017ae6c9ce76aae",
"inchikey": "WGIBEMRBLBGETQ-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cc(O)cc(Br)c1"
},
"smiles": "O=C(O)c1cc(O)cc(Br)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "11023",
"routeId": "sa_24adc0964d96eee075d7f0bc",
"moleculeId": "sa_701da92cca2d7546e36ddebd",
"parentId": "11017",
"isLeaf": false,
"molecule": {
"id": "sa_701da92cca2d7546e36ddebd",
"inchikey": "LDGZMPDLIYSAFD-UHFFFAOYSA-N",
"smiles": "Cc1ccc(NC(=O)C2(c3ccc4c(c3)OC(F)(F)O4)CC2)nc1Cl"
},
"smiles": "Cc1ccc(NC(=O)C2(c3ccc4c(c3)OC(F)(F)O4)CC2)nc1Cl",
"reactionStepId": "sa_ab52695d60be3b4d1f6058fa",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065500A1;0475;1660107\",\"rsmi\":\"Cl[C:8](=[O:9])[C:10]1([c:11]2[cH:12][c:13]3[c:14]([cH:15][cH:16]2)[O:17][C:18]([F:19])([F:20])[O:21]3)[CH2:22][CH2:23]1.[CH3:1][c:2]1[c:3]([Cl:4])[n:5][c:6]([NH2:7])[cH:24][cH:25]1>CCN(CC)CC.ClCCl>[CH3:1][c:2]1[c:3]([Cl:4])[n:5][c:6]([NH:7][C:8](=[O:9])[C:10]2([c:11]3[cH:12][c:13]4[c:14]([cH:15][cH:16]3)[O:17][C:18]([F:19])([F:20])[O:21]4)[CH2:22][CH2:23]2)[cH:24][cH:25]1\"},\"mapped_reaction_smiles\":\"Cl[C:8](=[O:9])[C:10]1([c:11]2[cH:12][c:13]3[c:14]([cH:15][cH:16]2)[O:17][C:18]([F:19])([F:20])[O:21]3)[CH2:22][CH2:23]1.[CH3:1][c:2]1[c:3]([Cl:4])[n:5][c:6]([NH2:7])[cH:24][cH:25]1>CCN(CC)CC.ClCCl>[CH3:1][c:2]1[c:3]([Cl:4])[n:5][c:6]([NH:7][C:8](=[O:9])[C:10]2([c:11]3[cH:12][c:13]4[c:14]([cH:15][cH:16]3)[O:17][C:18]([F:19])([F:20])[O:21]4)[CH2:22][CH2:23]2)[cH:24][cH:25]1\"}",
"reactionStep": {
"id": "sa_ab52695d60be3b4d1f6058fa",
"reactionHash": "aab33c8d8453efd5fb1904ac904f6c16cdb178cb8030918a9541fba69a444f17"
},
"children": [
{
"id": "11024",
"routeId": "sa_24adc0964d96eee075d7f0bc",
"moleculeId": "sa_2a374b8c063933a732a44bab",
"parentId": "11023",
"isLeaf": false,
"molecule": {
"id": "sa_2a374b8c063933a732a44bab",
"inchikey": "FVNYSBKXILOVTD-UHFFFAOYSA-N",
"smiles": "O=C(Cl)C1(c2ccc3c(c2)OC(F)(F)O3)CC1"
},
"smiles": "O=C(Cl)C1(c2ccc3c(c2)OC(F)(F)O3)CC1",
"reactionStepId": "sa_fa9c6006325da748c5c73ddb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065500A1;0469;1660104\",\"rsmi\":\"O=S(Cl)[Cl:3].O[C:2](=[O:1])[C:4]1([c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10]2)[O:11][C:12]([F:13])([F:14])[O:15]3)[CH2:16][CH2:17]1>CN(C)C=O>[O:1]=[C:2]([Cl:3])[C:4]1([c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10]2)[O:11][C:12]([F:13])([F:14])[O:15]3)[CH2:16][CH2:17]1\"},\"mapped_reaction_smiles\":\"O=S(Cl)[Cl:3].O[C:2](=[O:1])[C:4]1([c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10]2)[O:11][C:12]([F:13])([F:14])[O:15]3)[CH2:16][CH2:17]1>CN(C)C=O>[O:1]=[C:2]([Cl:3])[C:4]1([c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10]2)[O:11][C:12]([F:13])([F:14])[O:15]3)[CH2:16][CH2:17]1\"}",
"reactionStep": {
"id": "sa_fa9c6006325da748c5c73ddb",
"reactionHash": "370c588420ba1aaadcedad4b90612b8b1308d761811472858c6567b685f9e80c"
},
"children": [
{
"id": "11025",
"routeId": "sa_24adc0964d96eee075d7f0bc",
"moleculeId": "sa_cd67ce42f230ef1a4063353c",
"parentId": "11024",
"isLeaf": true,
"molecule": {
"id": "sa_cd67ce42f230ef1a4063353c",
"inchikey": "FYSNRJHAOHDILO-UHFFFAOYSA-N",
"smiles": "O=S(Cl)Cl"
},
"smiles": "O=S(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11026",
"routeId": "sa_24adc0964d96eee075d7f0bc",
"moleculeId": "sa_9be965c22871bbe5378075e7",
"parentId": "11024",
"isLeaf": true,
"molecule": {
"id": "sa_9be965c22871bbe5378075e7",
"inchikey": "IELWGOUPQRHXLS-UHFFFAOYSA-N",
"smiles": "O=C(O)C1(c2ccc3c(c2)OC(F)(F)O3)CC1"
},
"smiles": "O=C(O)C1(c2ccc3c(c2)OC(F)(F)O3)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "11027",
"routeId": "sa_24adc0964d96eee075d7f0bc",
"moleculeId": "sa_e141490976a2f1323659aa34",
"parentId": "11023",
"isLeaf": true,
"molecule": {
"id": "sa_e141490976a2f1323659aa34",
"inchikey": "KPZRCZMNXPBHEH-UHFFFAOYSA-N",
"smiles": "Cc1ccc(N)nc1Cl"
},
"smiles": "Cc1ccc(N)nc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}