Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)Cc1cc(CCC#N)ccc1-c1ccc(O)c(Cc2ccccc2)c1
InChiKey
IPPHBZYJELRYIK-UHFFFAOYSA-N
Route Signature
5c7a1f5577f408648fa08a94ef4ab86a597da17f9bcfaea664a0e4faae8f9592
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_788f9f367e22d8d8dd358db0",
"signature": "5c7a1f5577f408648fa08a94ef4ab86a597da17f9bcfaea664a0e4faae8f9592",
"contentHash": "7c180fa0f97e5001a9f021bb3506bc7bd521b23905ecc872ed55daf621cd2f8f",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_ee1fcffa09adf9f533465f80",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01475",
"moleculeId": "sa_c49f462297672d83f6d64cdd",
"smiles": "CC(C)Cc1cc(CCC#N)ccc1-c1ccc(O)c(Cc2ccccc2)c1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_c49f462297672d83f6d64cdd",
"inchikey": "IPPHBZYJELRYIK-UHFFFAOYSA-N",
"smiles": "CC(C)Cc1cc(CCC#N)ccc1-c1ccc(O)c(Cc2ccccc2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14357",
"routeId": "sa_788f9f367e22d8d8dd358db0",
"moleculeId": "sa_c49f462297672d83f6d64cdd",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c49f462297672d83f6d64cdd",
"inchikey": "IPPHBZYJELRYIK-UHFFFAOYSA-N",
"smiles": "CC(C)Cc1cc(CCC#N)ccc1-c1ccc(O)c(Cc2ccccc2)c1"
},
"smiles": "CC(C)Cc1cc(CCC#N)ccc1-c1ccc(O)c(Cc2ccccc2)c1",
"reactionStepId": "sa_ca2a16ba32392e427a49f99d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050215563A1;0121;287119\",\"rsmi\":\"C[O:18][c:17]1[c:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:8][c:7](-[c:6]2[c:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[cH:28][c:23]([CH2:24][CH2:25][C:26]#[N:27])[cH:22][cH:21]2)[cH:20][cH:19]1>BrB(Br)Br.ClCCl.O>[CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[c:6](-[c:7]2[cH:8][c:9]([CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17]([OH:18])[cH:19][cH:20]2)[cH:21][cH:22][c:23]([CH2:24][CH2:25][C:26]#[N:27])[cH:28]1\"},\"mapped_reaction_smiles\":\"C[O:18][c:17]1[c:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:8][c:7](-[c:6]2[c:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[cH:28][c:23]([CH2:24][CH2:25][C:26]#[N:27])[cH:22][cH:21]2)[cH:20][cH:19]1>BrB(Br)Br.ClCCl.O>[CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[c:6](-[c:7]2[cH:8][c:9]([CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17]([OH:18])[cH:19][cH:20]2)[cH:21][cH:22][c:23]([CH2:24][CH2:25][C:26]#[N:27])[cH:28]1\"}",
"reactionStep": {
"id": "sa_ca2a16ba32392e427a49f99d",
"reactionHash": "fe8c013276a4291fe5d59547bfb66f092d17e6663b026f4aa209971df4866114"
},
"children": [
{
"id": "14358",
"routeId": "sa_788f9f367e22d8d8dd358db0",
"moleculeId": "sa_465ca896ab02fe913415124c",
"parentId": "14357",
"isLeaf": false,
"molecule": {
"id": "sa_465ca896ab02fe913415124c",
"inchikey": "SGNAAOAODSMLKC-UHFFFAOYSA-N",
"smiles": "COc1ccc(-c2ccc(CCC#N)cc2CC(C)C)cc1Cc1ccccc1"
},
"smiles": "COc1ccc(-c2ccc(CCC#N)cc2CC(C)C)cc1Cc1ccccc1",
"reactionStepId": "sa_3d0e1dfce5f668f2cad77361",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050215563A1;0120;287118\",\"rsmi\":\"O=S(=O)(O[c:14]1[c:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[cH:20][c:21]([CH2:22][CH2:23][C:24]#[N:25])[cH:26][cH:27]1)C(F)(F)F.OB(O)[c:13]1[cH:12][c:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:3]([O:2][CH3:1])[cH:29][cH:28]1>CCO.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]1[c:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][c:13](-[c:14]2[c:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[cH:20][c:21]([CH2:22][CH2:23][C:24]#[N:25])[cH:26][cH:27]2)[cH:28][cH:29]1\"},\"mapped_reaction_smiles\":\"O=S(=O)(O[c:14]1[c:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[cH:20][c:21]([CH2:22][CH2:23][C:24]#[N:25])[cH:26][cH:27]1)C(F)(F)F.OB(O)[c:13]1[cH:12][c:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:3]([O:2][CH3:1])[cH:29][cH:28]1>CCO.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]1[c:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][c:13](-[c:14]2[c:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[cH:20][c:21]([CH2:22][CH2:23][C:24]#[N:25])[cH:26][cH:27]2)[cH:28][cH:29]1\"}",
"reactionStep": {
"id": "sa_3d0e1dfce5f668f2cad77361",
"reactionHash": "25ced8ae49aba4a114226ae02f2e0f718f5001c5fbba711fdc3110ffece9fb99"
},
"children": [
{
"id": "14359",
"routeId": "sa_788f9f367e22d8d8dd358db0",
"moleculeId": "sa_fc7975deda7ba53b62e1559e",
"parentId": "14358",
"isLeaf": true,
"molecule": {
"id": "sa_fc7975deda7ba53b62e1559e",
"inchikey": "LUGJHPYKFJPGJJ-UHFFFAOYSA-N",
"smiles": "CC(C)Cc1cc(CCC#N)ccc1OS(=O)(=O)C(F)(F)F"
},
"smiles": "CC(C)Cc1cc(CCC#N)ccc1OS(=O)(=O)C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14360",
"routeId": "sa_788f9f367e22d8d8dd358db0",
"moleculeId": "sa_b6be30bd4d5712f3ae4bf7d0",
"parentId": "14358",
"isLeaf": false,
"molecule": {
"id": "sa_b6be30bd4d5712f3ae4bf7d0",
"inchikey": "UAVVPTNWMCWFRE-UHFFFAOYSA-N",
"smiles": "COc1ccc(B(O)O)cc1Cc1ccccc1"
},
"smiles": "COc1ccc(B(O)O)cc1Cc1ccccc1",
"reactionStepId": "sa_360cf2667642b109b0eab8a3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050215563A1;0118;287116\",\"rsmi\":\"Br[c:13]1[cH:12][c:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:3]([O:2][CH3:1])[cH:18][cH:17]1.CO[B:14]([O:15]C)[O:16]C>C1CCOC1.O.[Li]CCCC.[Na+].O>[CH3:1][O:2][c:3]1[c:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][c:13]([B:14]([OH:15])[OH:16])[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"Br[c:13]1[cH:12][c:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:3]([O:2][CH3:1])[cH:18][cH:17]1.CO[B:14]([O:15]C)[O:16]C>C1CCOC1.O.[Li]CCCC.[Na+].O>[CH3:1][O:2][c:3]1[c:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][c:13]([B:14]([OH:15])[OH:16])[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_360cf2667642b109b0eab8a3",
"reactionHash": "e36b4eb85915e6abdfd4e7f07e2bae0fc3c4605aed249cbbdbc5a274fee440d9"
},
"children": [
{
"id": "14361",
"routeId": "sa_788f9f367e22d8d8dd358db0",
"moleculeId": "sa_3921eda8cccff81eb2f5828f",
"parentId": "14360",
"isLeaf": true,
"molecule": {
"id": "sa_3921eda8cccff81eb2f5828f",
"inchikey": "WRECIMRULFAWHA-UHFFFAOYSA-N",
"smiles": "COB(OC)OC"
},
"smiles": "COB(OC)OC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14362",
"routeId": "sa_788f9f367e22d8d8dd358db0",
"moleculeId": "sa_2e8ac07c3bef589ec0d22e2a",
"parentId": "14360",
"isLeaf": false,
"molecule": {
"id": "sa_2e8ac07c3bef589ec0d22e2a",
"inchikey": "XJJSSEXOKIYBPT-UHFFFAOYSA-N",
"smiles": "COc1ccc(Br)cc1Cc1ccccc1"
},
"smiles": "COc1ccc(Br)cc1Cc1ccccc1",
"reactionStepId": "sa_390a22c4458369eea32ea859",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050215563A1;0117;287115\",\"rsmi\":\"I[CH3:1].[OH:2][c:3]1[c:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][c:13]([Br:14])[cH:15][cH:16]1>CC(C)=O.ClCCl.N.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][c:3]1[c:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][c:13]([Br:14])[cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"I[CH3:1].[OH:2][c:3]1[c:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][c:13]([Br:14])[cH:15][cH:16]1>CC(C)=O.ClCCl.N.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][c:3]1[c:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][c:13]([Br:14])[cH:15][cH:16]1\"}",
"reactionStep": {
"id": "sa_390a22c4458369eea32ea859",
"reactionHash": "6bfc8707529c49bdfe5675448bb740ed17a0d0909353119b15701aca0538d236"
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"children": [
{
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"routeId": "sa_788f9f367e22d8d8dd358db0",
"moleculeId": "sa_667b5d3e290d0f5ee7a309b1",
"parentId": "14362",
"isLeaf": false,
"molecule": {
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"inchikey": "CWWDXXXNDJVDRH-UHFFFAOYSA-N",
"smiles": "Oc1ccc(Br)cc1Cc1ccccc1"
},
"smiles": "Oc1ccc(Br)cc1Cc1ccccc1",
"reactionStepId": "sa_a9649bddda9b6e165368189e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050215563A1;0116;287114\",\"rsmi\":\"O[CH:4]([c:3]1[c:2]([OH:1])[cH:15][cH:14][c:12]([Br:13])[cH:11]1)[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>CCOCC.CCOCC.CO.ClCCl.[Al+3].[Al+3].Cl.Cl.Cl.[HH].[HH].[HH].[HH].[Li+]>[OH:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:12]([Br:13])[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"O[CH:4]([c:3]1[c:2]([OH:1])[cH:15][cH:14][c:12]([Br:13])[cH:11]1)[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>CCOCC.CCOCC.CO.ClCCl.[Al+3].[Al+3].Cl.Cl.Cl.[HH].[HH].[HH].[HH].[Li+]>[OH:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:12]([Br:13])[cH:14][cH:15]1\"}",
"reactionStep": {
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"reactionHash": "edf8b2c0f20355ce5f27a2f43e4a43deaf8774e1ef67b0593ce59df21438174b"
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"children": [
{
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"routeId": "sa_788f9f367e22d8d8dd358db0",
"moleculeId": "sa_3a0a23edc661c21dd3bb5663",
"parentId": "14363",
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"molecule": {
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"inchikey": "FVSLBHWCCVFFHR-UHFFFAOYSA-N",
"smiles": "Oc1ccc(Br)cc1C(O)c1ccccc1"
},
"smiles": "Oc1ccc(Br)cc1C(O)c1ccccc1",
"reactionStepId": "sa_932985cc7d7b699130641a51",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050215563A1;0115;287113\",\"rsmi\":\"[OH:1][c:2]1[c:3]([C:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][c:13]([Br:14])[cH:15][cH:16]1>CO.B.[Na+]>[OH:1][c:2]1[c:3]([CH:4]([OH:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][c:13]([Br:14])[cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"[OH:1][c:2]1[c:3]([C:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][c:13]([Br:14])[cH:15][cH:16]1>CO.B.[Na+]>[OH:1][c:2]1[c:3]([CH:4]([OH:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][c:13]([Br:14])[cH:15][cH:16]1\"}",
"reactionStep": {
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"reactionHash": "be960627a4f2c2b6d4e6e7657f6c99108ece1cdc82cd581b0f0b191585451f89"
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"children": [
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"routeId": "sa_788f9f367e22d8d8dd358db0",
"moleculeId": "sa_ab86f85215f6e18d4b77d9bc",
"parentId": "14364",
"isLeaf": true,
"molecule": {
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"inchikey": "IVIICRNXAGUXLR-UHFFFAOYSA-N",
"smiles": "O=C(c1ccccc1)c1cc(Br)ccc1O"
},
"smiles": "O=C(c1ccccc1)c1cc(Br)ccc1O",
"reactionStepId": null,
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}
]
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]
},
{
"id": "14366",
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"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
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"molecule": {
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"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
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}
]
}
]
}
]
}
]
}
}