Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Nc1ccc(N2CCCCC2)cc1-c1cc(NC(=O)c2cccc(C(F)(F)F)c2)ccn1
InChiKey
CUTKSUUKCZXWSS-UHFFFAOYSA-N
Route Signature
e7ad6e7eeddba62712a993d21dbd249e6f541d69736e45df238b26188c929882
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_8ea10305f526c3fd3a59ad07",
"signature": "e7ad6e7eeddba62712a993d21dbd249e6f541d69736e45df238b26188c929882",
"contentHash": "52cf8a20fa98845167963fa90ace77234a3ca9c7958248f4043c9b6371b9888e",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_706929f4c85007e43942747e",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-01499",
"moleculeId": "sa_3a52aceb31bfddf798c9801b",
"smiles": "Nc1ccc(N2CCCCC2)cc1-c1cc(NC(=O)c2cccc(C(F)(F)F)c2)ccn1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_3a52aceb31bfddf798c9801b",
"inchikey": "CUTKSUUKCZXWSS-UHFFFAOYSA-N",
"smiles": "Nc1ccc(N2CCCCC2)cc1-c1cc(NC(=O)c2cccc(C(F)(F)F)c2)ccn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "1498",
"routeId": "sa_8ea10305f526c3fd3a59ad07",
"moleculeId": "sa_3a52aceb31bfddf798c9801b",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_3a52aceb31bfddf798c9801b",
"inchikey": "CUTKSUUKCZXWSS-UHFFFAOYSA-N",
"smiles": "Nc1ccc(N2CCCCC2)cc1-c1cc(NC(=O)c2cccc(C(F)(F)F)c2)ccn1"
},
"smiles": "Nc1ccc(N2CCCCC2)cc1-c1cc(NC(=O)c2cccc(C(F)(F)F)c2)ccn1",
"reactionStepId": "sa_c9ed4a93b7dbe2ac88d36429",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130336920A1;0653;1463846\",\"rsmi\":\"CC1(C)OB([c:3]2[c:2]([NH2:1])[cH:32][cH:31][c:24]([N:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[cH:23]2)OC1(C)C.Cl[c:4]1[n:5][cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21]2)[cH:22]1>CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.COCCOC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O>[NH2:1][c:2]1[c:3](-[c:4]2[n:5][cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]3[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21]3)[cH:22]2)[cH:23][c:24]([N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[cH:31][cH:32]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:3]2[c:2]([NH2:1])[cH:32][cH:31][c:24]([N:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[cH:23]2)OC1(C)C.Cl[c:4]1[n:5][cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21]2)[cH:22]1>CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.COCCOC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O>[NH2:1][c:2]1[c:3](-[c:4]2[n:5][cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]3[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21]3)[cH:22]2)[cH:23][c:24]([N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[cH:31][cH:32]1\"}",
"reactionStep": {
"id": "sa_c9ed4a93b7dbe2ac88d36429",
"reactionHash": "421774ab6c108cb845688f2be92438352f663a9e23f8985d327f975300a0e8f9"
},
"children": [
{
"id": "1499",
"routeId": "sa_8ea10305f526c3fd3a59ad07",
"moleculeId": "sa_4649d857df01c58e2058f1e7",
"parentId": "1498",
"isLeaf": false,
"molecule": {
"id": "sa_4649d857df01c58e2058f1e7",
"inchikey": "HYFDFWYXHKHDBC-UHFFFAOYSA-N",
"smiles": "O=C(Nc1ccnc(Cl)c1)c1cccc(C(F)(F)F)c1"
},
"smiles": "O=C(Nc1ccnc(Cl)c1)c1cccc(C(F)(F)F)c1",
"reactionStepId": "sa_da6242148307232b90088c31",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130336920A1;0652;1463845\",\"rsmi\":\"Cl[C:2](=[O:1])[c:11]1[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19][cH:20]1.[NH2:3][c:4]1[cH:5][c:6]([Cl:7])[n:8][cH:9][cH:10]1>CCN(C(C)C)C(C)C.ClCCl>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([Cl:7])[n:8][cH:9][cH:10]1)[c:11]1[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[c:11]1[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19][cH:20]1.[NH2:3][c:4]1[cH:5][c:6]([Cl:7])[n:8][cH:9][cH:10]1>CCN(C(C)C)C(C)C.ClCCl>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([Cl:7])[n:8][cH:9][cH:10]1)[c:11]1[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_da6242148307232b90088c31",
"reactionHash": "52e397fa105a6ff8fd39b7a53ebf09757c683d10fe5b58ced719c213051a79bd"
},
"children": [
{
"id": "1500",
"routeId": "sa_8ea10305f526c3fd3a59ad07",
"moleculeId": "sa_766c1fe5d5fda96babf90cd3",
"parentId": "1499",
"isLeaf": true,
"molecule": {
"id": "sa_766c1fe5d5fda96babf90cd3",
"inchikey": "BLBDTBCGPHPIJK-UHFFFAOYSA-N",
"smiles": "Nc1ccnc(Cl)c1"
},
"smiles": "Nc1ccnc(Cl)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1501",
"routeId": "sa_8ea10305f526c3fd3a59ad07",
"moleculeId": "sa_6ae5a7aeeedf4ee14b718507",
"parentId": "1499",
"isLeaf": true,
"molecule": {
"id": "sa_6ae5a7aeeedf4ee14b718507",
"inchikey": "RUJYJCANMOTJMO-UHFFFAOYSA-N",
"smiles": "O=C(Cl)c1cccc(C(F)(F)F)c1"
},
"smiles": "O=C(Cl)c1cccc(C(F)(F)F)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "1502",
"routeId": "sa_8ea10305f526c3fd3a59ad07",
"moleculeId": "sa_3cd7dd4dacf0eb187b68e7a8",
"parentId": "1498",
"isLeaf": false,
"molecule": {
"id": "sa_3cd7dd4dacf0eb187b68e7a8",
"inchikey": "QQSVXOZGNWJXJU-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cc(N3CCCCC3)ccc2N)OC1(C)C"
},
"smiles": "CC1(C)OB(c2cc(N3CCCCC3)ccc2N)OC1(C)C",
"reactionStepId": "sa_cf22b577503dbabdf781beeb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130336920A1;0651;1463844\",\"rsmi\":\"O=[N+:8]([O-])[c:7]1[c:6]([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:20]([CH3:21])([CH3:22])[O:19]2)[cH:18][c:11]([N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:10][cH:9]1>C.CCOC(C)=O.[Pd]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]([NH2:8])[cH:9][cH:10][c:11]([N:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18]2)[O:19][C:20]1([CH3:21])[CH3:22]\"},\"mapped_reaction_smiles\":\"O=[N+:8]([O-])[c:7]1[c:6]([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:20]([CH3:21])([CH3:22])[O:19]2)[cH:18][c:11]([N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:10][cH:9]1>C.CCOC(C)=O.[Pd]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]([NH2:8])[cH:9][cH:10][c:11]([N:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18]2)[O:19][C:20]1([CH3:21])[CH3:22]\"}",
"reactionStep": {
"id": "sa_cf22b577503dbabdf781beeb",
"reactionHash": "6e27b4999dae9569d8441bc101210471544b4768299c78b7ed68fd38d1e2f352"
},
"children": [
{
"id": "1503",
"routeId": "sa_8ea10305f526c3fd3a59ad07",
"moleculeId": "sa_7ea6d525159f20d1bb52d777",
"parentId": "1502",
"isLeaf": false,
"molecule": {
"id": "sa_7ea6d525159f20d1bb52d777",
"inchikey": "ATOXGVCTPWNKTK-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cc(N3CCCCC3)ccc2[N+](=O)[O-])OC1(C)C"
},
"smiles": "CC1(C)OB(c2cc(N3CCCCC3)ccc2[N+](=O)[O-])OC1(C)C",
"reactionStepId": "sa_80e8976807c83d0a56b38cd6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130336920A1;0272;1463672\",\"rsmi\":\"Br[c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:22]([CH3:23])([CH3:24])[O:21]2)OC1(C)C>CC(=O)O.CS(C)=O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]([N:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[cH:20]2)[O:21][C:22]1([CH3:23])[CH3:24]\"},\"mapped_reaction_smiles\":\"Br[c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:22]([CH3:23])([CH3:24])[O:21]2)OC1(C)C>CC(=O)O.CS(C)=O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]([N:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[cH:20]2)[O:21][C:22]1([CH3:23])[CH3:24]\"}",
"reactionStep": {
"id": "sa_80e8976807c83d0a56b38cd6",
"reactionHash": "aa0ba27d58abcc7440df6ad36f4790483c17af0058b8ce213d28048019fc7e3e"
},
"children": [
{
"id": "1504",
"routeId": "sa_8ea10305f526c3fd3a59ad07",
"moleculeId": "sa_8b6bb60ea37a04c336145afa",
"parentId": "1503",
"isLeaf": false,
"molecule": {
"id": "sa_8b6bb60ea37a04c336145afa",
"inchikey": "IFPALIOJOQUXQY-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(N2CCCCC2)cc1Br"
},
"smiles": "O=[N+]([O-])c1ccc(N2CCCCC2)cc1Br",
"reactionStepId": "sa_9887a9ec9918fc100bb81b29",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130336920A1;0271;1463671\",\"rsmi\":\"F[c:8]1[cH:7][c:5]([Br:6])[c:4]([N+:2](=[O:1])[O-:3])[cH:16][cH:15]1.[NH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([Br:6])[cH:7][c:8]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"F[c:8]1[cH:7][c:5]([Br:6])[c:4]([N+:2](=[O:1])[O-:3])[cH:16][cH:15]1.[NH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([Br:6])[cH:7][c:8]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][cH:16]1\"}",
"reactionStep": {
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"reactionHash": "85c78bfcfc864df7e73e7d9184ed0ebfc90944014de343e8c37f9b6b9af0f83b"
},
"children": [
{
"id": "1505",
"routeId": "sa_8ea10305f526c3fd3a59ad07",
"moleculeId": "sa_60b03dbd902de8f42159b182",
"parentId": "1504",
"isLeaf": true,
"molecule": {
"id": "sa_60b03dbd902de8f42159b182",
"inchikey": "NQRYJNQNLNOLGT-UHFFFAOYSA-N",
"smiles": "C1CCNCC1"
},
"smiles": "C1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1506",
"routeId": "sa_8ea10305f526c3fd3a59ad07",
"moleculeId": "sa_00f13ce0aa60a53df3808b4e",
"parentId": "1504",
"isLeaf": true,
"molecule": {
"id": "sa_00f13ce0aa60a53df3808b4e",
"inchikey": "VGYVBEJDXIPSDL-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(F)cc1Br"
},
"smiles": "O=[N+]([O-])c1ccc(F)cc1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "1507",
"routeId": "sa_8ea10305f526c3fd3a59ad07",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "1503",
"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,
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"children": []
}
]
}
]
}
]
}
}