Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCc1nc2cnc3ccsc3c2n1[C@H]1CC[C@H](CC#N)CC1
InChiKey
QRVZXIUWEAWTGH-JOCQHMNTSA-N
Route Signature
b62e4eeb573c7908fdc815661127f26f6469786c0c3e7cccfc7b74991c230316
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_60cf9b6829dea5cf9bd7d768",
"signature": "b62e4eeb573c7908fdc815661127f26f6469786c0c3e7cccfc7b74991c230316",
"contentHash": "774bd6e71cfd886ac2cb27d781c8ae96987a2e95afcafa015de13468f848ae9d",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_fc2d1f36233b5feb5920678a",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00257",
"moleculeId": "sa_a738feda9a701f4cf5b2c719",
"smiles": "CCc1nc2cnc3ccsc3c2n1[C@H]1CC[C@H](CC#N)CC1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_a738feda9a701f4cf5b2c719",
"inchikey": "QRVZXIUWEAWTGH-JOCQHMNTSA-N",
"smiles": "CCc1nc2cnc3ccsc3c2n1[C@H]1CC[C@H](CC#N)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "3742",
"routeId": "sa_60cf9b6829dea5cf9bd7d768",
"moleculeId": "sa_a738feda9a701f4cf5b2c719",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_a738feda9a701f4cf5b2c719",
"inchikey": "QRVZXIUWEAWTGH-JOCQHMNTSA-N",
"smiles": "CCc1nc2cnc3ccsc3c2n1[C@H]1CC[C@H](CC#N)CC1"
},
"smiles": "CCc1nc2cnc3ccsc3c2n1[C@H]1CC[C@H](CC#N)CC1",
"reactionStepId": "sa_135537516f0879c491946ecd",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09181271B2;0833;1692000\",\"rsmi\":\"CCO[C:3](OCC)(OCC)[CH2:2][CH3:1].[NH2:4][c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][s:11][c:12]2[c:13]1[NH:14][C@H:15]1[CH2:16][CH2:17][C@H:18]([CH2:19][C:20]#[N:21])[CH2:22][CH2:23]1>CC(=O)O.CO>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[cH:6][n:7][c:8]3[cH:9][cH:10][s:11][c:12]3[c:13]2[n:14]1[C@H:15]1[CH2:16][CH2:17][C@H:18]([CH2:19][C:20]#[N:21])[CH2:22][CH2:23]1\"},\"mapped_reaction_smiles\":\"CCO[C:3](OCC)(OCC)[CH2:2][CH3:1].[NH2:4][c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][s:11][c:12]2[c:13]1[NH:14][C@H:15]1[CH2:16][CH2:17][C@H:18]([CH2:19][C:20]#[N:21])[CH2:22][CH2:23]1>CC(=O)O.CO>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[cH:6][n:7][c:8]3[cH:9][cH:10][s:11][c:12]3[c:13]2[n:14]1[C@H:15]1[CH2:16][CH2:17][C@H:18]([CH2:19][C:20]#[N:21])[CH2:22][CH2:23]1\"}",
"reactionStep": {
"id": "sa_135537516f0879c491946ecd",
"reactionHash": "bc91d4c0d7e4eaa724ef2730c25df891d3605c174d6745079f1743adcb2ce0ff"
},
"children": [
{
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"routeId": "sa_60cf9b6829dea5cf9bd7d768",
"moleculeId": "sa_c00979205342075ab6a7cade",
"parentId": "3742",
"isLeaf": true,
"molecule": {
"id": "sa_c00979205342075ab6a7cade",
"inchikey": "FGWYWKIOMUZSQF-UHFFFAOYSA-N",
"smiles": "CCOC(CC)(OCC)OCC"
},
"smiles": "CCOC(CC)(OCC)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3744",
"routeId": "sa_60cf9b6829dea5cf9bd7d768",
"moleculeId": "sa_e4ae31a9183a4317e999c9d9",
"parentId": "3742",
"isLeaf": false,
"molecule": {
"id": "sa_e4ae31a9183a4317e999c9d9",
"inchikey": "KZXWSIPGMMXBAS-XYPYZODXSA-N",
"smiles": "N#CC[C@H]1CC[C@H](Nc2c(N)cnc3ccsc23)CC1"
},
"smiles": "N#CC[C@H]1CC[C@H](Nc2c(N)cnc3ccsc23)CC1",
"reactionStepId": "sa_aaf9071004d41b0df0e4a8b2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09181271B2;0598;1691851\",\"rsmi\":\"O=[N+:18]([O-])[c:17]1[c:9]([NH:8][C@H:7]2[CH2:6][CH2:5][C@H:4]([CH2:3][C:2]#[N:1])[CH2:20][CH2:19]2)[c:10]2[s:11][cH:12][cH:13][c:14]2[n:15][cH:16]1>CO.[Pd]>[N:1]#[C:2][CH2:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([NH:8][c:9]2[c:10]3[s:11][cH:12][cH:13][c:14]3[n:15][cH:16][c:17]2[NH2:18])[CH2:19][CH2:20]1\"},\"mapped_reaction_smiles\":\"O=[N+:18]([O-])[c:17]1[c:9]([NH:8][C@H:7]2[CH2:6][CH2:5][C@H:4]([CH2:3][C:2]#[N:1])[CH2:20][CH2:19]2)[c:10]2[s:11][cH:12][cH:13][c:14]2[n:15][cH:16]1>CO.[Pd]>[N:1]#[C:2][CH2:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([NH:8][c:9]2[c:10]3[s:11][cH:12][cH:13][c:14]3[n:15][cH:16][c:17]2[NH2:18])[CH2:19][CH2:20]1\"}",
"reactionStep": {
"id": "sa_aaf9071004d41b0df0e4a8b2",
"reactionHash": "892cca7ab16a8b9ef2c0e5dc26a727cbc4e8b87c35619f6f534d74283fe4ef9b"
},
"children": [
{
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"moleculeId": "sa_3014546bf136be7fb97d35f3",
"parentId": "3744",
"isLeaf": false,
"molecule": {
"id": "sa_3014546bf136be7fb97d35f3",
"inchikey": "MFQKBTJDQLOBNG-XYPYZODXSA-N",
"smiles": "N#CC[C@H]1CC[C@H](Nc2c([N+](=O)[O-])cnc3ccsc23)CC1"
},
"smiles": "N#CC[C@H]1CC[C@H](Nc2c([N+](=O)[O-])cnc3ccsc23)CC1",
"reactionStepId": "sa_a14f3b586b242b4ec3931dd9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09181271B2;0596;1691850\",\"rsmi\":\"CS(=O)(=O)O[CH2:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([NH:8][c:9]2[c:10]3[s:11][cH:12][cH:13][c:14]3[n:15][cH:16][c:17]2[N+:18](=[O:19])[O-:20])[CH2:21][CH2:22]1.[N:1]#[CH:2]>CCOC(C)=O.CS(C)=O.[Na+]>[N:1]#[C:2][CH2:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([NH:8][c:9]2[c:10]3[s:11][cH:12][cH:13][c:14]3[n:15][cH:16][c:17]2[N+:18](=[O:19])[O-:20])[CH2:21][CH2:22]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[CH2:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([NH:8][c:9]2[c:10]3[s:11][cH:12][cH:13][c:14]3[n:15][cH:16][c:17]2[N+:18](=[O:19])[O-:20])[CH2:21][CH2:22]1.[N:1]#[CH:2]>CCOC(C)=O.CS(C)=O.[Na+]>[N:1]#[C:2][CH2:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([NH:8][c:9]2[c:10]3[s:11][cH:12][cH:13][c:14]3[n:15][cH:16][c:17]2[N+:18](=[O:19])[O-:20])[CH2:21][CH2:22]1\"}",
"reactionStep": {
"id": "sa_a14f3b586b242b4ec3931dd9",
"reactionHash": "c4eacc3935bde22919b5f5c73c81d8cf178da685cb5e16a85c56d2563177f2b6"
},
"children": [
{
"id": "3746",
"routeId": "sa_60cf9b6829dea5cf9bd7d768",
"moleculeId": "sa_cde7b5ca4b4030a8efc0eda5",
"parentId": "3745",
"isLeaf": false,
"molecule": {
"id": "sa_cde7b5ca4b4030a8efc0eda5",
"inchikey": "DQGHYPRWTJXVAH-XYPYZODXSA-N",
"smiles": "CS(=O)(=O)OC[C@H]1CC[C@H](Nc2c([N+](=O)[O-])cnc3ccsc23)CC1"
},
"smiles": "CS(=O)(=O)OC[C@H]1CC[C@H](Nc2c([N+](=O)[O-])cnc3ccsc23)CC1",
"reactionStepId": "sa_b8f1f83e1a0b23054d7ff78a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09181271B2;0594;1691849\",\"rsmi\":\"Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([NH:11][c:12]2[c:13]3[s:14][cH:15][cH:16][c:17]3[n:18][cH:19][c:20]2[N+:21](=[O:22])[O-:23])[CH2:24][CH2:25]1>CCN(C(C)C)C(C)C.ClCCl.O>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([NH:11][c:12]2[c:13]3[s:14][cH:15][cH:16][c:17]3[n:18][cH:19][c:20]2[N+:21](=[O:22])[O-:23])[CH2:24][CH2:25]1\"},\"mapped_reaction_smiles\":\"Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([NH:11][c:12]2[c:13]3[s:14][cH:15][cH:16][c:17]3[n:18][cH:19][c:20]2[N+:21](=[O:22])[O-:23])[CH2:24][CH2:25]1>CCN(C(C)C)C(C)C.ClCCl.O>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([NH:11][c:12]2[c:13]3[s:14][cH:15][cH:16][c:17]3[n:18][cH:19][c:20]2[N+:21](=[O:22])[O-:23])[CH2:24][CH2:25]1\"}",
"reactionStep": {
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"reactionHash": "ee2bf39ed937eb1beecf9cb430ab3c5b46524868f2a39929fd0cae221136f100"
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"children": [
{
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"routeId": "sa_60cf9b6829dea5cf9bd7d768",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "3746",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "3748",
"routeId": "sa_60cf9b6829dea5cf9bd7d768",
"moleculeId": "sa_82d7f04f712f54c58387241b",
"parentId": "3746",
"isLeaf": false,
"molecule": {
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"inchikey": "VQERDAJAKQXHIY-MGCOHNPYSA-N",
"smiles": "O=[N+]([O-])c1cnc2ccsc2c1N[C@H]1CC[C@H](CO)CC1"
},
"smiles": "O=[N+]([O-])c1cnc2ccsc2c1N[C@H]1CC[C@H](CO)CC1",
"reactionStepId": "sa_f989e4f9fbffb04a8cf078a9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09181271B2;0592;1691848\",\"rsmi\":\"Cl[c:12]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][cH:9][s:10][c:11]21.[NH2:13][C@H:14]1[CH2:15][CH2:16][C@H:17]([CH2:18][OH:19])[CH2:20][CH2:21]1>CC(C)O.CCN(C(C)C)C(C)C>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][cH:9][s:10][c:11]2[c:12]1[NH:13][C@H:14]1[CH2:15][CH2:16][C@H:17]([CH2:18][OH:19])[CH2:20][CH2:21]1\"},\"mapped_reaction_smiles\":\"Cl[c:12]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][cH:9][s:10][c:11]21.[NH2:13][C@H:14]1[CH2:15][CH2:16][C@H:17]([CH2:18][OH:19])[CH2:20][CH2:21]1>CC(C)O.CCN(C(C)C)C(C)C>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][cH:9][s:10][c:11]2[c:12]1[NH:13][C@H:14]1[CH2:15][CH2:16][C@H:17]([CH2:18][OH:19])[CH2:20][CH2:21]1\"}",
"reactionStep": {
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"reactionHash": "dd32715a5adb2d5abb587d6d2406bfed833136bfec09e7152d6c1d4c5d9d6fdb"
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"children": [
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"moleculeId": "sa_961ab0e0919aad2c67f2b2f2",
"parentId": "3748",
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"molecule": {
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"inchikey": "GHUJZOFJZVGTSN-LJGSYFOKSA-N",
"smiles": "N[C@H]1CC[C@H](CO)CC1"
},
"smiles": "N[C@H]1CC[C@H](CO)CC1",
"reactionStepId": null,
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{
"id": "3750",
"routeId": "sa_60cf9b6829dea5cf9bd7d768",
"moleculeId": "sa_38543ce037944ff34a2d3f76",
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"molecule": {
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"inchikey": "RKZKGVJIROTNKJ-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cnc2ccsc2c1Cl"
},
"smiles": "O=[N+]([O-])c1cnc2ccsc2c1Cl",
"reactionStepId": "sa_21221c4f5120eed798a7c7f9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09181271B2;0584;1691844\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:13].O[c:12]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][cH:9][s:10][c:11]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][cH:9][s:10][c:11]2[c:12]1[Cl:13]\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:13].O[c:12]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][cH:9][s:10][c:11]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][cH:9][s:10][c:11]2[c:12]1[Cl:13]\"}",
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"children": [
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"molecule": {
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"smiles": "O=c1c([N+](=O)[O-])c[nH]c2ccsc12"
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"smiles": "O=[N+]([O-])c1cnc2ccsc2c1O",
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{
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"molecule": {
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"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
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"smiles": "O=P(Cl)(Cl)Cl",
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}
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]
},
{
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"molecule": {
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"inchikey": "LELOWRISYMNNSU-UHFFFAOYSA-N",
"smiles": "C#N"
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}
]
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]
}
]
}
}