Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
N#Cc1ncc(Oc2ccc3c(c2)CCN(C2CCC2)CC3)cn1
InChiKey
MCKMVLIDYPWYSX-UHFFFAOYSA-N
Route Signature
168bd4c642f864600ebdc1e0094fe8d926b7cb337f258654b3b601b63f56f26a
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_35265e0277b6977bd7fc030d",
"signature": "168bd4c642f864600ebdc1e0094fe8d926b7cb337f258654b3b601b63f56f26a",
"contentHash": "64cee0fd795292dec8e72171af174140567a54fac53acaf44ec2f8382e934c5e",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_db4af311374cba5e6e97011e",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01690",
"moleculeId": "sa_85dd0ddf1ad1da073e00d4fc",
"smiles": "N#Cc1ncc(Oc2ccc3c(c2)CCN(C2CCC2)CC3)cn1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_85dd0ddf1ad1da073e00d4fc",
"inchikey": "MCKMVLIDYPWYSX-UHFFFAOYSA-N",
"smiles": "N#Cc1ncc(Oc2ccc3c(c2)CCN(C2CCC2)CC3)cn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10394",
"routeId": "sa_35265e0277b6977bd7fc030d",
"moleculeId": "sa_85dd0ddf1ad1da073e00d4fc",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_85dd0ddf1ad1da073e00d4fc",
"inchikey": "MCKMVLIDYPWYSX-UHFFFAOYSA-N",
"smiles": "N#Cc1ncc(Oc2ccc3c(c2)CCN(C2CCC2)CC3)cn1"
},
"smiles": "N#Cc1ncc(Oc2ccc3c(c2)CCN(C2CCC2)CC3)cn1",
"reactionStepId": "sa_0e3f792197e216ad917f6560",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08207331B2;0312;1205478\",\"rsmi\":\"Br[c:6]1[cH:5][n:4][c:3]([C:2]#[N:1])[n:24][cH:23]1.[OH:7][c:8]1[cH:9][c:10]2[c:11]([cH:12][cH:13]1)[CH2:14][CH2:15][N:16]([CH:17]1[CH2:18][CH2:19][CH2:20]1)[CH2:21][CH2:22]2>[Cu]Br.[HH].[Na+].c1ccncc1>[N:1]#[C:2][c:3]1[n:4][cH:5][c:6]([O:7][c:8]2[cH:9][c:10]3[c:11]([cH:12][cH:13]2)[CH2:14][CH2:15][N:16]([CH:17]2[CH2:18][CH2:19][CH2:20]2)[CH2:21][CH2:22]3)[cH:23][n:24]1\"},\"mapped_reaction_smiles\":\"Br[c:6]1[cH:5][n:4][c:3]([C:2]#[N:1])[n:24][cH:23]1.[OH:7][c:8]1[cH:9][c:10]2[c:11]([cH:12][cH:13]1)[CH2:14][CH2:15][N:16]([CH:17]1[CH2:18][CH2:19][CH2:20]1)[CH2:21][CH2:22]2>[Cu]Br.[HH].[Na+].c1ccncc1>[N:1]#[C:2][c:3]1[n:4][cH:5][c:6]([O:7][c:8]2[cH:9][c:10]3[c:11]([cH:12][cH:13]2)[CH2:14][CH2:15][N:16]([CH:17]2[CH2:18][CH2:19][CH2:20]2)[CH2:21][CH2:22]3)[cH:23][n:24]1\"}",
"reactionStep": {
"id": "sa_0e3f792197e216ad917f6560",
"reactionHash": "d170752dd0c22c01badee54858ef84e351937d3d5eb64a2164c36a9f87909f51"
},
"children": [
{
"id": "10395",
"routeId": "sa_35265e0277b6977bd7fc030d",
"moleculeId": "sa_8673dd496eeaaf7789768860",
"parentId": "10394",
"isLeaf": false,
"molecule": {
"id": "sa_8673dd496eeaaf7789768860",
"inchikey": "KODOGLMDJREIOW-UHFFFAOYSA-N",
"smiles": "Oc1ccc2c(c1)CCN(C1CCC1)CC2"
},
"smiles": "Oc1ccc2c(c1)CCN(C1CCC1)CC2",
"reactionStepId": "sa_e4ced45fac2be729b69b7578",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08207331B2;0196;1205445\",\"rsmi\":\"c1ccc(C[O:1][c:2]2[cH:3][c:4]3[c:5]([cH:6][cH:7]2)[CH2:8][CH2:9][N:10]([CH:11]2[CH2:12][CH2:13][CH2:14]2)[CH2:15][CH2:16]3)cc1>C1CCOC1.CCO.[Pd]>[OH:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[CH2:8][CH2:9][N:10]([CH:11]1[CH2:12][CH2:13][CH2:14]1)[CH2:15][CH2:16]2\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:1][c:2]2[cH:3][c:4]3[c:5]([cH:6][cH:7]2)[CH2:8][CH2:9][N:10]([CH:11]2[CH2:12][CH2:13][CH2:14]2)[CH2:15][CH2:16]3)cc1>C1CCOC1.CCO.[Pd]>[OH:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[CH2:8][CH2:9][N:10]([CH:11]1[CH2:12][CH2:13][CH2:14]1)[CH2:15][CH2:16]2\"}",
"reactionStep": {
"id": "sa_e4ced45fac2be729b69b7578",
"reactionHash": "ef00fcea3e5a3b623fb2aa65b46056e0b63147d1a3938fc450fcdc3aae74f20d"
},
"children": [
{
"id": "10396",
"routeId": "sa_35265e0277b6977bd7fc030d",
"moleculeId": "sa_ccf505dc7ff30f9a1c0213e4",
"parentId": "10395",
"isLeaf": false,
"molecule": {
"id": "sa_ccf505dc7ff30f9a1c0213e4",
"inchikey": "IFLIPLANALCYLX-UHFFFAOYSA-N",
"smiles": "c1ccc(COc2ccc3c(c2)CCN(C2CCC2)CC3)cc1"
},
"smiles": "c1ccc(COc2ccc3c(c2)CCN(C2CCC2)CC3)cc1",
"reactionStepId": "sa_7e50a2d41d58606f54afa53d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08207331B2;0192;1205443\",\"rsmi\":\"O=[C:16]1[CH2:17][CH2:18][CH2:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][c:9]3[c:10]([cH:11][cH:12]2)[CH2:13][CH2:14][NH:15][CH2:20][CH2:21]3)[cH:22][cH:23]1>CC(=O)O.CC(=O)OB(OC(C)=O)OC(C)=O.ClCCl.O=C(O)O.[Na+].[Na+].[Na+]>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][c:9]3[c:10]([cH:11][cH:12]2)[CH2:13][CH2:14][N:15]([CH:16]2[CH2:17][CH2:18][CH2:19]2)[CH2:20][CH2:21]3)[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"O=[C:16]1[CH2:17][CH2:18][CH2:19]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][c:9]3[c:10]([cH:11][cH:12]2)[CH2:13][CH2:14][NH:15][CH2:20][CH2:21]3)[cH:22][cH:23]1>CC(=O)O.CC(=O)OB(OC(C)=O)OC(C)=O.ClCCl.O=C(O)O.[Na+].[Na+].[Na+]>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][c:9]3[c:10]([cH:11][cH:12]2)[CH2:13][CH2:14][N:15]([CH:16]2[CH2:17][CH2:18][CH2:19]2)[CH2:20][CH2:21]3)[cH:22][cH:23]1\"}",
"reactionStep": {
"id": "sa_7e50a2d41d58606f54afa53d",
"reactionHash": "a1822a9408bdd847a54d51088359ab7af384141007b2c5595f1e69c5260ccca0"
},
"children": [
{
"id": "10397",
"routeId": "sa_35265e0277b6977bd7fc030d",
"moleculeId": "sa_11c13b41c5d10e682529ae15",
"parentId": "10396",
"isLeaf": false,
"molecule": {
"id": "sa_11c13b41c5d10e682529ae15",
"inchikey": "DPRCEQIDVGCQRH-UHFFFAOYSA-N",
"smiles": "c1ccc(COc2ccc3c(c2)CCNCC3)cc1"
},
"smiles": "c1ccc(COc2ccc3c(c2)CCNCC3)cc1",
"reactionStepId": "sa_4b632d2a09794c0603ba39d3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08207331B2;0135;1205421\",\"rsmi\":\"CC(C)(C)OC(=O)[N:15]1[CH2:14][CH2:13][c:10]2[c:9]([cH:8][c:7]([O:6][CH2:5][c:4]3[cH:3][cH:2][cH:1][cH:19][cH:18]3)[cH:12][cH:11]2)[CH2:17][CH2:16]1>ClCCl.O=C(O)C(F)(F)F>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][c:9]3[c:10]([cH:11][cH:12]2)[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:15]1[CH2:14][CH2:13][c:10]2[c:9]([cH:8][c:7]([O:6][CH2:5][c:4]3[cH:3][cH:2][cH:1][cH:19][cH:18]3)[cH:12][cH:11]2)[CH2:17][CH2:16]1>ClCCl.O=C(O)C(F)(F)F>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][c:9]3[c:10]([cH:11][cH:12]2)[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)[cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_4b632d2a09794c0603ba39d3",
"reactionHash": "641c748e9418908ae6e1715b5c2a77ec1ff4b3dc452679fc3dd2147cc67e0686"
},
"children": [
{
"id": "10398",
"routeId": "sa_35265e0277b6977bd7fc030d",
"moleculeId": "sa_051d9c2d126f9fd0afd07f42",
"parentId": "10397",
"isLeaf": false,
"molecule": {
"id": "sa_051d9c2d126f9fd0afd07f42",
"inchikey": "KSIWVMOQAURIFM-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCc2ccc(OCc3ccccc3)cc2CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCc2ccc(OCc3ccccc3)cc2CC1",
"reactionStepId": "sa_7cd3b9f0ad8c509fb4493a5a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08207331B2;0134;1205420\",\"rsmi\":\"Br[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[c:12]([cH:13][c:14]([OH:15])[cH:23][cH:24]2)[CH2:25][CH2:26]1>CCC(C)=O.O=C(O)O.I.[K+].[K+].[K+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[c:12]([cH:13][c:14]([O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][cH:24]2)[CH2:25][CH2:26]1\"},\"mapped_reaction_smiles\":\"Br[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[c:12]([cH:13][c:14]([OH:15])[cH:23][cH:24]2)[CH2:25][CH2:26]1>CCC(C)=O.O=C(O)O.I.[K+].[K+].[K+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[c:12]([cH:13][c:14]([O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][cH:24]2)[CH2:25][CH2:26]1\"}",
"reactionStep": {
"id": "sa_7cd3b9f0ad8c509fb4493a5a",
"reactionHash": "b377ff7af78255265c6e143a2c84e1efd3497009b76c1ccc7edadcd250a34140"
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"children": [
{
"id": "10399",
"routeId": "sa_35265e0277b6977bd7fc030d",
"moleculeId": "sa_4ff2e4de9d80150de333c065",
"parentId": "10398",
"isLeaf": true,
"molecule": {
"id": "sa_4ff2e4de9d80150de333c065",
"inchikey": "AGEZXYOZHKGVCM-UHFFFAOYSA-N",
"smiles": "BrCc1ccccc1"
},
"smiles": "BrCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10400",
"routeId": "sa_35265e0277b6977bd7fc030d",
"moleculeId": "sa_51289f901c99ce3d3188d05c",
"parentId": "10398",
"isLeaf": true,
"molecule": {
"id": "sa_51289f901c99ce3d3188d05c",
"inchikey": "CUVFQINKSGIQML-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCc2ccc(O)cc2CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCc2ccc(O)cc2CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
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]
},
{
"id": "10401",
"routeId": "sa_35265e0277b6977bd7fc030d",
"moleculeId": "sa_b21cdb7ecf949177283a856f",
"parentId": "10396",
"isLeaf": true,
"molecule": {
"id": "sa_b21cdb7ecf949177283a856f",
"inchikey": "SHQSVMDWKBRBGB-UHFFFAOYSA-N",
"smiles": "O=C1CCC1"
},
"smiles": "O=C1CCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
},
{
"id": "10402",
"routeId": "sa_35265e0277b6977bd7fc030d",
"moleculeId": "sa_841d5126b657d5b999747f27",
"parentId": "10394",
"isLeaf": false,
"molecule": {
"id": "sa_841d5126b657d5b999747f27",
"inchikey": "VPQICCOHFSGBMA-UHFFFAOYSA-N",
"smiles": "N#Cc1ncc(Br)cn1"
},
"smiles": "N#Cc1ncc(Br)cn1",
"reactionStepId": "sa_42b2833a0ca6a39d52050be9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08207331B2;0151;1205426\",\"rsmi\":\"Cl[c:3]1[n:4][cH:5][c:6]([Br:7])[cH:8][n:9]1.[N:1]#[CH:2]>CN(C)C=O.O.[Na+]>[N:1]#[C:2][c:3]1[n:4][cH:5][c:6]([Br:7])[cH:8][n:9]1\"},\"mapped_reaction_smiles\":\"Cl[c:3]1[n:4][cH:5][c:6]([Br:7])[cH:8][n:9]1.[N:1]#[CH:2]>CN(C)C=O.O.[Na+]>[N:1]#[C:2][c:3]1[n:4][cH:5][c:6]([Br:7])[cH:8][n:9]1\"}",
"reactionStep": {
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"reactionHash": "be9ca1fe32ea956dc6f9671be0ed6349c41f7129c96dd7b5d524d1a57cd5b36c"
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"children": [
{
"id": "10403",
"routeId": "sa_35265e0277b6977bd7fc030d",
"moleculeId": "sa_5995aff3aeff665a1f3e984d",
"parentId": "10402",
"isLeaf": true,
"molecule": {
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"inchikey": "LELOWRISYMNNSU-UHFFFAOYSA-N",
"smiles": "C#N"
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"smiles": "C#N",
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{
"id": "10404",
"routeId": "sa_35265e0277b6977bd7fc030d",
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"molecule": {
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"inchikey": "XPGIBDJXEVAVTO-UHFFFAOYSA-N",
"smiles": "Clc1ncc(Br)cn1"
},
"smiles": "Clc1ncc(Br)cn1",
"reactionStepId": null,
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}
]
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]
}
}