Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCn1c(CC2CC2c2ccc(Br)cc2)nn(Cc2ccc(C(C)(C)C)cc2)c1=O
InChiKey
FPHMPWDWWVLZGU-UHFFFAOYSA-N
Route Signature
35da0023089874d4a3bd5f82461ae61cf76dfb5af3432c18e69f7640bae446bd
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_a1211fa7c5e736116acd0781",
"signature": "35da0023089874d4a3bd5f82461ae61cf76dfb5af3432c18e69f7640bae446bd",
"contentHash": "becd11690ad5da34a6d3aa77c478522f4d812c656dea8b560081f787520e80d8",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_212d69f0df7d20351942d946",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00325",
"moleculeId": "sa_31b5aa41c6e56b8db213760f",
"smiles": "CCn1c(CC2CC2c2ccc(Br)cc2)nn(Cc2ccc(C(C)(C)C)cc2)c1=O",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_31b5aa41c6e56b8db213760f",
"inchikey": "FPHMPWDWWVLZGU-UHFFFAOYSA-N",
"smiles": "CCn1c(CC2CC2c2ccc(Br)cc2)nn(Cc2ccc(C(C)(C)C)cc2)c1=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13072",
"routeId": "sa_a1211fa7c5e736116acd0781",
"moleculeId": "sa_31b5aa41c6e56b8db213760f",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_31b5aa41c6e56b8db213760f",
"inchikey": "FPHMPWDWWVLZGU-UHFFFAOYSA-N",
"smiles": "CCn1c(CC2CC2c2ccc(Br)cc2)nn(Cc2ccc(C(C)(C)C)cc2)c1=O"
},
"smiles": "CCn1c(CC2CC2c2ccc(Br)cc2)nn(Cc2ccc(C(C)(C)C)cc2)c1=O",
"reactionStepId": "sa_41b313e95278658699865781",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150080412A1;0694;1667947\",\"rsmi\":\"Br[CH2:7][c:8]1[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]1.[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[nH:6][n:18][c:19]1[CH2:20][CH:21]1[CH2:22][CH:23]1[c:24]1[cH:25][cH:26][c:27]([Br:28])[cH:29][cH:30]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[n:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]2)[n:18][c:19]1[CH2:20][CH:21]1[CH2:22][CH:23]1[c:24]1[cH:25][cH:26][c:27]([Br:28])[cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"Br[CH2:7][c:8]1[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]1.[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[nH:6][n:18][c:19]1[CH2:20][CH:21]1[CH2:22][CH:23]1[c:24]1[cH:25][cH:26][c:27]([Br:28])[cH:29][cH:30]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[n:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]2)[n:18][c:19]1[CH2:20][CH:21]1[CH2:22][CH:23]1[c:24]1[cH:25][cH:26][c:27]([Br:28])[cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_41b313e95278658699865781",
"reactionHash": "dd368bd6cf73e4bb63198e80888ec9ef664372dccfe1c7a4fbdb05170ef97b13"
},
"children": [
{
"id": "13073",
"routeId": "sa_a1211fa7c5e736116acd0781",
"moleculeId": "sa_48a87276773cd7800981932f",
"parentId": "13072",
"isLeaf": false,
"molecule": {
"id": "sa_48a87276773cd7800981932f",
"inchikey": "CADMICCPIRQNQO-UHFFFAOYSA-N",
"smiles": "CCn1c(CC2CC2c2ccc(Br)cc2)n[nH]c1=O"
},
"smiles": "CCn1c(CC2CC2c2ccc(Br)cc2)n[nH]c1=O",
"reactionStepId": "sa_126d9c62fe8dd5fee262491f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150080412A1;0693;1667946\",\"rsmi\":\"O=[C:8]([NH:7][NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[CH2:9][CH:10]1[CH2:11][CH:12]1[c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]1>CO.[K+].O>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[nH:6][n:7][c:8]1[CH2:9][CH:10]1[CH2:11][CH:12]1[c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"O=[C:8]([NH:7][NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[CH2:9][CH:10]1[CH2:11][CH:12]1[c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]1>CO.[K+].O>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[nH:6][n:7][c:8]1[CH2:9][CH:10]1[CH2:11][CH:12]1[c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_126d9c62fe8dd5fee262491f",
"reactionHash": "bdc27aff7813ea5c1d40c73f93210da69e03edc4a18e58ca95a4825334a6e7b5"
},
"children": [
{
"id": "13074",
"routeId": "sa_a1211fa7c5e736116acd0781",
"moleculeId": "sa_e00c913d622ac88310609ddd",
"parentId": "13073",
"isLeaf": false,
"molecule": {
"id": "sa_e00c913d622ac88310609ddd",
"inchikey": "TVMTXQYNWLDXCJ-UHFFFAOYSA-N",
"smiles": "CCNC(=O)NNC(=O)CC1CC1c1ccc(Br)cc1"
},
"smiles": "CCNC(=O)NNC(=O)CC1CC1c1ccc(Br)cc1",
"reactionStepId": "sa_27f713f7a78fa24400c9001f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150080412A1;0692;1667945\",\"rsmi\":\"[CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][NH:7][C:8](=[O:9])[CH2:10][CH:11]1[CH2:12][CH:13]1[c:14]1[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]1>C1CCOC1>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][NH:7][C:8](=[O:9])[CH2:10][CH:11]1[CH2:12][CH:13]1[c:14]1[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][NH:7][C:8](=[O:9])[CH2:10][CH:11]1[CH2:12][CH:13]1[c:14]1[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]1>C1CCOC1>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][NH:7][C:8](=[O:9])[CH2:10][CH:11]1[CH2:12][CH:13]1[c:14]1[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_27f713f7a78fa24400c9001f",
"reactionHash": "ccc087add2e4ac19684f6d851e53a9d6fc789164c571d84124753e3444ea05c7"
},
"children": [
{
"id": "13075",
"routeId": "sa_a1211fa7c5e736116acd0781",
"moleculeId": "sa_c4ec894dac09b2fed822b365",
"parentId": "13074",
"isLeaf": false,
"molecule": {
"id": "sa_c4ec894dac09b2fed822b365",
"inchikey": "WBXLGJSBLNVXIR-UHFFFAOYSA-N",
"smiles": "NNC(=O)CC1CC1c1ccc(Br)cc1"
},
"smiles": "NNC(=O)CC1CC1c1ccc(Br)cc1",
"reactionStepId": "sa_057a954c3c850106c80a611a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150080412A1;0691;1667944\",\"rsmi\":\"O[C:3](=[O:4])[CH2:5][CH:6]1[CH2:7][CH:8]1[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1.[NH2:1][NH2:2]>C1CCOC1.O.O=C(n1ccnc1)n1ccnc1>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][CH:6]1[CH2:7][CH:8]1[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[CH2:5][CH:6]1[CH2:7][CH:8]1[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1.[NH2:1][NH2:2]>C1CCOC1.O.O=C(n1ccnc1)n1ccnc1>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][CH:6]1[CH2:7][CH:8]1[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1\"}",
"reactionStep": {
"id": "sa_057a954c3c850106c80a611a",
"reactionHash": "17b5ff8c9785eebe2882d295d0d715f34071410673ce20dbfca8a9f2eeb602c9"
},
"children": [
{
"id": "13076",
"routeId": "sa_a1211fa7c5e736116acd0781",
"moleculeId": "sa_681b90bfe3789a310096845b",
"parentId": "13075",
"isLeaf": true,
"molecule": {
"id": "sa_681b90bfe3789a310096845b",
"inchikey": "OAKJQQAXSVQMHS-UHFFFAOYSA-N",
"smiles": "NN"
},
"smiles": "NN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13077",
"routeId": "sa_a1211fa7c5e736116acd0781",
"moleculeId": "sa_50eb5d71c33e8bb8a290990c",
"parentId": "13075",
"isLeaf": false,
"molecule": {
"id": "sa_50eb5d71c33e8bb8a290990c",
"inchikey": "YZTRUGQDICDRPV-UHFFFAOYSA-N",
"smiles": "O=C(O)CC1CC1c1ccc(Br)cc1"
},
"smiles": "O=C(O)CC1CC1c1ccc(Br)cc1",
"reactionStepId": "sa_4145c7a7ed7aef50e100d950",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150080412A1;0690;1667943\",\"rsmi\":\"CCOC(C)=[O:1].N#[C:2][CH2:4][CH:5]1[CH2:6][CH:7]1[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1.[OH2:3]>CCO.Cl.[K+].O>[O:1]=[C:2]([OH:3])[CH2:4][CH:5]1[CH2:6][CH:7]1[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"CCOC(C)=[O:1].N#[C:2][CH2:4][CH:5]1[CH2:6][CH:7]1[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1.[OH2:3]>CCO.Cl.[K+].O>[O:1]=[C:2]([OH:3])[CH2:4][CH:5]1[CH2:6][CH:7]1[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1\"}",
"reactionStep": {
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"reactionHash": "a14e9b53491accca8c0394161466cec8ea1357f129b0b05462883ab12b7b6826"
},
"children": [
{
"id": "13078",
"routeId": "sa_a1211fa7c5e736116acd0781",
"moleculeId": "sa_bb267165b920f66105ee0acc",
"parentId": "13077",
"isLeaf": false,
"molecule": {
"id": "sa_bb267165b920f66105ee0acc",
"inchikey": "MUJIYKAFDAKPFJ-UHFFFAOYSA-N",
"smiles": "N#CCC1CC1c1ccc(Br)cc1"
},
"smiles": "N#CCC1CC1c1ccc(Br)cc1",
"reactionStepId": "sa_db9d3faf3ff3d06e77e1df62",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150080412A1;0689;1667942\",\"rsmi\":\"O[CH2:3][CH:4]1[CH2:5][CH:6]1[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1.[N:1]#[CH:2]>CCN(CC)CC.CCOC(C)=O.CS(=O)(=O)Cl.ClCCl.[K+]>[N:1]#[C:2][CH2:3][CH:4]1[CH2:5][CH:6]1[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"O[CH2:3][CH:4]1[CH2:5][CH:6]1[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1.[N:1]#[CH:2]>CCN(CC)CC.CCOC(C)=O.CS(=O)(=O)Cl.ClCCl.[K+]>[N:1]#[C:2][CH2:3][CH:4]1[CH2:5][CH:6]1[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1\"}",
"reactionStep": {
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"reactionHash": "76da2df50ff2e84cc651cf89aca6c19f28bf00d6d9d079ec330a75c9e9f810be"
},
"children": [
{
"id": "13079",
"routeId": "sa_a1211fa7c5e736116acd0781",
"moleculeId": "sa_75d6071455cae66ba2c9f777",
"parentId": "13078",
"isLeaf": true,
"molecule": {
"id": "sa_75d6071455cae66ba2c9f777",
"inchikey": "AVYSEWDQKFGYMF-UHFFFAOYSA-N",
"smiles": "OCC1CC1c1ccc(Br)cc1"
},
"smiles": "OCC1CC1c1ccc(Br)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13080",
"routeId": "sa_a1211fa7c5e736116acd0781",
"moleculeId": "sa_5995aff3aeff665a1f3e984d",
"parentId": "13078",
"isLeaf": true,
"molecule": {
"id": "sa_5995aff3aeff665a1f3e984d",
"inchikey": "LELOWRISYMNNSU-UHFFFAOYSA-N",
"smiles": "C#N"
},
"smiles": "C#N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13081",
"routeId": "sa_a1211fa7c5e736116acd0781",
"moleculeId": "sa_6bf30f725089b74d691fc82c",
"parentId": "13077",
"isLeaf": true,
"molecule": {
"id": "sa_6bf30f725089b74d691fc82c",
"inchikey": "XEKOWRVHYACXOJ-UHFFFAOYSA-N",
"smiles": "CCOC(C)=O"
},
"smiles": "CCOC(C)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13082",
"routeId": "sa_a1211fa7c5e736116acd0781",
"moleculeId": "sa_106b35b8a76bbe73829a0a69",
"parentId": "13077",
"isLeaf": true,
"molecule": {
"id": "sa_106b35b8a76bbe73829a0a69",
"inchikey": "XLYOFNOQVPJJNP-UHFFFAOYSA-N",
"smiles": "O"
},
"smiles": "O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "13083",
"routeId": "sa_a1211fa7c5e736116acd0781",
"moleculeId": "sa_1f6b618862390fbeac2c8a25",
"parentId": "13074",
"isLeaf": true,
"molecule": {
"id": "sa_1f6b618862390fbeac2c8a25",
"inchikey": "WUDNUHPRLBTKOJ-UHFFFAOYSA-N",
"smiles": "CCN=C=O"
},
"smiles": "CCN=C=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "13084",
"routeId": "sa_a1211fa7c5e736116acd0781",
"moleculeId": "sa_50732c59046b6c772e3ee36b",
"parentId": "13072",
"isLeaf": true,
"molecule": {
"id": "sa_50732c59046b6c772e3ee36b",
"inchikey": "QZNQSIHCDAGZIA-UHFFFAOYSA-N",
"smiles": "CC(C)(C)c1ccc(CBr)cc1"
},
"smiles": "CC(C)(C)c1ccc(CBr)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}