Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)CNC(=O)C1CCN(c2nc(-c3ccnc(Cl)c3)c(-c3ccc(F)cc3)c3cnccc23)CC1
InChiKey
WYIIUUKLAIZXGX-UHFFFAOYSA-N
Route Signature
9e3143fc73cb0ff750e52ee5fa3d2915ae33eb52c7ec48095e3f319498f61f64
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_d75bfe3d0f769a26562c5611",
"signature": "9e3143fc73cb0ff750e52ee5fa3d2915ae33eb52c7ec48095e3f319498f61f64",
"contentHash": "bb80b265ef450144110d819f759a78bb10108d643e53744c6c29144bdfcaaed3",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_d41f86c05a08eaee9d43b316",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00557",
"moleculeId": "sa_a636a4327e1b4d4e45e205ec",
"smiles": "CC(C)CNC(=O)C1CCN(c2nc(-c3ccnc(Cl)c3)c(-c3ccc(F)cc3)c3cnccc23)CC1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_a636a4327e1b4d4e45e205ec",
"inchikey": "WYIIUUKLAIZXGX-UHFFFAOYSA-N",
"smiles": "CC(C)CNC(=O)C1CCN(c2nc(-c3ccnc(Cl)c3)c(-c3ccc(F)cc3)c3cnccc23)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13473",
"routeId": "sa_d75bfe3d0f769a26562c5611",
"moleculeId": "sa_a636a4327e1b4d4e45e205ec",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_a636a4327e1b4d4e45e205ec",
"inchikey": "WYIIUUKLAIZXGX-UHFFFAOYSA-N",
"smiles": "CC(C)CNC(=O)C1CCN(c2nc(-c3ccnc(Cl)c3)c(-c3ccc(F)cc3)c3cnccc23)CC1"
},
"smiles": "CC(C)CNC(=O)C1CCN(c2nc(-c3ccnc(Cl)c3)c(-c3ccc(F)cc3)c3cnccc23)CC1",
"reactionStepId": "sa_0517164138482a651a3147fa",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120142685A1;0688;1224033\",\"rsmi\":\"Br[c:22]1[c:14](-[c:15]2[cH:16][c:17]([Cl:18])[n:19][cH:20][cH:21]2)[n:13][c:12]([N:11]2[CH2:10][CH2:9][CH:8]([C:6]([NH:5][CH2:4][CH:2]([CH3:1])[CH3:3])=[O:7])[CH2:37][CH2:36]2)[c:35]2[c:30]1[cH:31][n:32][cH:33][cH:34]2.OB(O)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1>COCCOC.ClCCl.Cl[Pd]Cl.O=C(O)O.[Fe+2].[Na+].[Na+]>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][c:14](-[c:15]3[cH:16][c:17]([Cl:18])[n:19][cH:20][cH:21]3)[c:22](-[c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]3)[c:30]3[cH:31][n:32][cH:33][cH:34][c:35]23)[CH2:36][CH2:37]1\"},\"mapped_reaction_smiles\":\"Br[c:22]1[c:14](-[c:15]2[cH:16][c:17]([Cl:18])[n:19][cH:20][cH:21]2)[n:13][c:12]([N:11]2[CH2:10][CH2:9][CH:8]([C:6]([NH:5][CH2:4][CH:2]([CH3:1])[CH3:3])=[O:7])[CH2:37][CH2:36]2)[c:35]2[c:30]1[cH:31][n:32][cH:33][cH:34]2.OB(O)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1>COCCOC.ClCCl.Cl[Pd]Cl.O=C(O)O.[Fe+2].[Na+].[Na+]>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][c:14](-[c:15]3[cH:16][c:17]([Cl:18])[n:19][cH:20][cH:21]3)[c:22](-[c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]3)[c:30]3[cH:31][n:32][cH:33][cH:34][c:35]23)[CH2:36][CH2:37]1\"}",
"reactionStep": {
"id": "sa_0517164138482a651a3147fa",
"reactionHash": "85c6e97f541bc7c5408cfce47e8c97d182f44092a90c5d82e596574e4c018b3a"
},
"children": [
{
"id": "13474",
"routeId": "sa_d75bfe3d0f769a26562c5611",
"moleculeId": "sa_3ec5abb3ae71125bbdf2213d",
"parentId": "13473",
"isLeaf": false,
"molecule": {
"id": "sa_3ec5abb3ae71125bbdf2213d",
"inchikey": "ACTDPHSVOZWGRV-UHFFFAOYSA-N",
"smiles": "CC(C)CNC(=O)C1CCN(c2nc(-c3ccnc(Cl)c3)c(Br)c3cnccc23)CC1"
},
"smiles": "CC(C)CNC(=O)C1CCN(c2nc(-c3ccnc(Cl)c3)c(Br)c3cnccc23)CC1",
"reactionStepId": "sa_f2c9f44fa64c41865abcf94e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120142685A1;0686;1224032\",\"rsmi\":\"O[C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][c:14](-[c:15]3[cH:16][c:17]([Cl:18])[n:19][cH:20][cH:21]3)[c:22]([Br:23])[c:24]3[cH:25][n:26][cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1.[CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5]>CN(C)C=O.ClCCl.F[PH](F)(F)(F)(F)F.c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][c:14](-[c:15]3[cH:16][c:17]([Cl:18])[n:19][cH:20][cH:21]3)[c:22]([Br:23])[c:24]3[cH:25][n:26][cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1\"},\"mapped_reaction_smiles\":\"O[C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][c:14](-[c:15]3[cH:16][c:17]([Cl:18])[n:19][cH:20][cH:21]3)[c:22]([Br:23])[c:24]3[cH:25][n:26][cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1.[CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5]>CN(C)C=O.ClCCl.F[PH](F)(F)(F)(F)F.c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][c:14](-[c:15]3[cH:16][c:17]([Cl:18])[n:19][cH:20][cH:21]3)[c:22]([Br:23])[c:24]3[cH:25][n:26][cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1\"}",
"reactionStep": {
"id": "sa_f2c9f44fa64c41865abcf94e",
"reactionHash": "7202a79388503a4fa68288bc900e78f5d6d7510ccf0076a5111cebea905954a6"
},
"children": [
{
"id": "13475",
"routeId": "sa_d75bfe3d0f769a26562c5611",
"moleculeId": "sa_7c48bb9f07df84f8b9fd5ad9",
"parentId": "13474",
"isLeaf": true,
"molecule": {
"id": "sa_7c48bb9f07df84f8b9fd5ad9",
"inchikey": "KDSNLYIMUZNERS-UHFFFAOYSA-N",
"smiles": "CC(C)CN"
},
"smiles": "CC(C)CN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13476",
"routeId": "sa_d75bfe3d0f769a26562c5611",
"moleculeId": "sa_aa56e8715f9abda509512f5d",
"parentId": "13474",
"isLeaf": false,
"molecule": {
"id": "sa_aa56e8715f9abda509512f5d",
"inchikey": "OLRBDWVZGNOEPR-UHFFFAOYSA-N",
"smiles": "O=C(O)C1CCN(c2nc(-c3ccnc(Cl)c3)c(Br)c3cnccc23)CC1"
},
"smiles": "O=C(O)C1CCN(c2nc(-c3ccnc(Cl)c3)c(Br)c3cnccc23)CC1",
"reactionStepId": "sa_76cddb84076b5a7138595c19",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120142685A1;0685;1224031\",\"rsmi\":\"C[O:3][C:2](=[O:1])[CH:4]1[CH2:5][CH2:6][N:7]([c:8]2[n:9][c:10](-[c:11]3[cH:12][c:13]([Cl:14])[n:15][cH:16][cH:17]3)[c:18]([Br:19])[c:20]3[cH:21][n:22][cH:23][cH:24][c:25]23)[CH2:26][CH2:27]1>C1CCOC1.CCOCC.Cl.O.[Li+].O>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][N:7]([c:8]2[n:9][c:10](-[c:11]3[cH:12][c:13]([Cl:14])[n:15][cH:16][cH:17]3)[c:18]([Br:19])[c:20]3[cH:21][n:22][cH:23][cH:24][c:25]23)[CH2:26][CH2:27]1\"},\"mapped_reaction_smiles\":\"C[O:3][C:2](=[O:1])[CH:4]1[CH2:5][CH2:6][N:7]([c:8]2[n:9][c:10](-[c:11]3[cH:12][c:13]([Cl:14])[n:15][cH:16][cH:17]3)[c:18]([Br:19])[c:20]3[cH:21][n:22][cH:23][cH:24][c:25]23)[CH2:26][CH2:27]1>C1CCOC1.CCOCC.Cl.O.[Li+].O>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][N:7]([c:8]2[n:9][c:10](-[c:11]3[cH:12][c:13]([Cl:14])[n:15][cH:16][cH:17]3)[c:18]([Br:19])[c:20]3[cH:21][n:22][cH:23][cH:24][c:25]23)[CH2:26][CH2:27]1\"}",
"reactionStep": {
"id": "sa_76cddb84076b5a7138595c19",
"reactionHash": "fad7147c4193fc0290ff24c102ec8d8c970ebc9ddd9bc8d035940d76bdeb1eb1"
},
"children": [
{
"id": "13477",
"routeId": "sa_d75bfe3d0f769a26562c5611",
"moleculeId": "sa_7476979b26ee3e0c4f5a3847",
"parentId": "13476",
"isLeaf": false,
"molecule": {
"id": "sa_7476979b26ee3e0c4f5a3847",
"inchikey": "ORGSZCNOIPYHMC-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CCN(c2nc(-c3ccnc(Cl)c3)c(Br)c3cnccc23)CC1"
},
"smiles": "COC(=O)C1CCN(c2nc(-c3ccnc(Cl)c3)c(Br)c3cnccc23)CC1",
"reactionStepId": "sa_bb46c38c697ce74ba50de16f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120142685A1;0683;1224030\",\"rsmi\":\"Br[Br:20].[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][N:8]([c:9]2[n:10][c:11](-[c:12]3[cH:13][c:14]([Cl:15])[n:16][cH:17][cH:18]3)[cH:19][c:21]3[cH:22][n:23][cH:24][cH:25][c:26]23)[CH2:27][CH2:28]1>ClCCl>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][N:8]([c:9]2[n:10][c:11](-[c:12]3[cH:13][c:14]([Cl:15])[n:16][cH:17][cH:18]3)[c:19]([Br:20])[c:21]3[cH:22][n:23][cH:24][cH:25][c:26]23)[CH2:27][CH2:28]1\"},\"mapped_reaction_smiles\":\"Br[Br:20].[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][N:8]([c:9]2[n:10][c:11](-[c:12]3[cH:13][c:14]([Cl:15])[n:16][cH:17][cH:18]3)[cH:19][c:21]3[cH:22][n:23][cH:24][cH:25][c:26]23)[CH2:27][CH2:28]1>ClCCl>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][N:8]([c:9]2[n:10][c:11](-[c:12]3[cH:13][c:14]([Cl:15])[n:16][cH:17][cH:18]3)[c:19]([Br:20])[c:21]3[cH:22][n:23][cH:24][cH:25][c:26]23)[CH2:27][CH2:28]1\"}",
"reactionStep": {
"id": "sa_bb46c38c697ce74ba50de16f",
"reactionHash": "2eab5227118af5da85045c8631fe3a4ba15865c57f4b9a8f8c3634b01802ac52"
},
"children": [
{
"id": "13478",
"routeId": "sa_d75bfe3d0f769a26562c5611",
"moleculeId": "sa_24211e89e565c162ea935f73",
"parentId": "13477",
"isLeaf": true,
"molecule": {
"id": "sa_24211e89e565c162ea935f73",
"inchikey": "GDTBXPJZTBHREO-UHFFFAOYSA-N",
"smiles": "BrBr"
},
"smiles": "BrBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13479",
"routeId": "sa_d75bfe3d0f769a26562c5611",
"moleculeId": "sa_500809f5d9c9d40e5868741c",
"parentId": "13477",
"isLeaf": false,
"molecule": {
"id": "sa_500809f5d9c9d40e5868741c",
"inchikey": "NDYIWTNUDFLGMH-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CCN(c2nc(-c3ccnc(Cl)c3)cc3cnccc23)CC1"
},
"smiles": "COC(=O)C1CCN(c2nc(-c3ccnc(Cl)c3)cc3cnccc23)CC1",
"reactionStepId": "sa_1fcf848079812db3391439b0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120142685A1;0304;1224017\",\"rsmi\":\"Cl[c:9]1[n:10][c:11](-[c:12]2[cH:13][c:14]([Cl:15])[n:16][cH:17][cH:18]2)[cH:19][c:20]2[cH:21][n:22][cH:23][cH:24][c:25]12.[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][NH:8][CH2:26][CH2:27]1>CCN(CC)CC.CS(C)=O.O>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][N:8]([c:9]2[n:10][c:11](-[c:12]3[cH:13][c:14]([Cl:15])[n:16][cH:17][cH:18]3)[cH:19][c:20]3[cH:21][n:22][cH:23][cH:24][c:25]23)[CH2:26][CH2:27]1\"},\"mapped_reaction_smiles\":\"Cl[c:9]1[n:10][c:11](-[c:12]2[cH:13][c:14]([Cl:15])[n:16][cH:17][cH:18]2)[cH:19][c:20]2[cH:21][n:22][cH:23][cH:24][c:25]12.[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][NH:8][CH2:26][CH2:27]1>CCN(CC)CC.CS(C)=O.O>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][N:8]([c:9]2[n:10][c:11](-[c:12]3[cH:13][c:14]([Cl:15])[n:16][cH:17][cH:18]3)[cH:19][c:20]3[cH:21][n:22][cH:23][cH:24][c:25]23)[CH2:26][CH2:27]1\"}",
"reactionStep": {
"id": "sa_1fcf848079812db3391439b0",
"reactionHash": "981e4c9b79ee856518b7b0d177175a553e700832824ec4c9b76291f207940f8a"
},
"children": [
{
"id": "13480",
"routeId": "sa_d75bfe3d0f769a26562c5611",
"moleculeId": "sa_ece6290240f20dc163436aa3",
"parentId": "13479",
"isLeaf": false,
"molecule": {
"id": "sa_ece6290240f20dc163436aa3",
"inchikey": "FKXPJANSDWNORP-UHFFFAOYSA-N",
"smiles": "Clc1cc(-c2cc3cnccc3c(Cl)n2)ccn1"
},
"smiles": "Clc1cc(-c2cc3cnccc3c(Cl)n2)ccn1",
"reactionStepId": "sa_1b4ba06624964018bbdcc445",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120142685A1;0220;1224013\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:16].O[c:15]1[c:14]2[c:9]([cH:8][c:7](-[c:6]3[cH:5][cH:4][n:3][c:2]([Cl:1])[cH:18]3)[n:17]1)[cH:10][n:11][cH:12][cH:13]2>C[N+](C)(C)C.Cl>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[cH:10][n:11][cH:12][cH:13][c:14]3[c:15]([Cl:16])[n:17]2)[cH:18]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:16].O[c:15]1[c:14]2[c:9]([cH:8][c:7](-[c:6]3[cH:5][cH:4][n:3][c:2]([Cl:1])[cH:18]3)[n:17]1)[cH:10][n:11][cH:12][cH:13]2>C[N+](C)(C)C.Cl>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[cH:10][n:11][cH:12][cH:13][c:14]3[c:15]([Cl:16])[n:17]2)[cH:18]1\"}",
"reactionStep": {
"id": "sa_1b4ba06624964018bbdcc445",
"reactionHash": "cb9e7a1e36472b2d0980023551cc78b662395258ffd7347315258ec399003bdf"
},
"children": [
{
"id": "13481",
"routeId": "sa_d75bfe3d0f769a26562c5611",
"moleculeId": "sa_bd2fb377127db7ed82fbf444",
"parentId": "13480",
"isLeaf": true,
"molecule": {
"id": "sa_bd2fb377127db7ed82fbf444",
"inchikey": "CIIGWQKDXFJDDD-UHFFFAOYSA-N",
"smiles": "Oc1nc(-c2ccnc(Cl)c2)cc2cnccc12"
},
"smiles": "Oc1nc(-c2ccnc(Cl)c2)cc2cnccc12",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13482",
"routeId": "sa_d75bfe3d0f769a26562c5611",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "13480",
"isLeaf": true,
"molecule": {
"id": "sa_312a7cd3d48a055e9bc98180",
"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13483",
"routeId": "sa_d75bfe3d0f769a26562c5611",
"moleculeId": "sa_4ba724ccd428bd8b94851ff2",
"parentId": "13479",
"isLeaf": true,
"molecule": {
"id": "sa_4ba724ccd428bd8b94851ff2",
"inchikey": "RZVWBASHHLFBJF-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CCNCC1"
},
"smiles": "COC(=O)C1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
},
{
"id": "13484",
"routeId": "sa_d75bfe3d0f769a26562c5611",
"moleculeId": "sa_973ab17588f80aae8a908d2f",
"parentId": "13473",
"isLeaf": true,
"molecule": {
"id": "sa_973ab17588f80aae8a908d2f",
"inchikey": "LBUNNMJLXWQQBY-UHFFFAOYSA-N",
"smiles": "OB(O)c1ccc(F)cc1"
},
"smiles": "OB(O)c1ccc(F)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}