Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O[C@@H]1CCCC[C@H]1Nc1nc2ccc(Cn3cnc(Br)c3)cc2s1
InChiKey
QMHZKVVEHCRCIK-TZMCWYRMSA-N
Route Signature
58403fd5985e9b3f59c1328eb374b0cf17568bc57e535c0de7124ca746ab2273
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_302d7b1ce2922e7809872e57",
"signature": "58403fd5985e9b3f59c1328eb374b0cf17568bc57e535c0de7124ca746ab2273",
"contentHash": "160184a164cd70b3fa38583d261de22305d11cbb6b62831f0d76015afd9eee69",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_93392a7da6f03f7b24ff0bda",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-07594",
"moleculeId": "sa_937d2f101a2cba362a5d1a95",
"smiles": "O[C@@H]1CCCC[C@H]1Nc1nc2ccc(Cn3cnc(Br)c3)cc2s1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_937d2f101a2cba362a5d1a95",
"inchikey": "QMHZKVVEHCRCIK-TZMCWYRMSA-N",
"smiles": "O[C@@H]1CCCC[C@H]1Nc1nc2ccc(Cn3cnc(Br)c3)cc2s1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "8362",
"routeId": "sa_302d7b1ce2922e7809872e57",
"moleculeId": "sa_937d2f101a2cba362a5d1a95",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_937d2f101a2cba362a5d1a95",
"inchikey": "QMHZKVVEHCRCIK-TZMCWYRMSA-N",
"smiles": "O[C@@H]1CCCC[C@H]1Nc1nc2ccc(Cn3cnc(Br)c3)cc2s1"
},
"smiles": "O[C@@H]1CCCC[C@H]1Nc1nc2ccc(Cn3cnc(Br)c3)cc2s1",
"reactionStepId": "sa_ced84e7c29fed7783c2e43d6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150196566A1;2186;1721429\",\"rsmi\":\"CS(=O)[c:9]1[n:10][c:11]2[c:12]([cH:13][c:14]([CH2:15][n:16]3[cH:17][n:18][c:19]([Br:20])[cH:21]3)[cH:22][cH:23]2)[s:24]1.[OH:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]1[NH2:8]>CC(=O)N(C)C.CCN(C(C)C)C(C)C.O>[OH:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]1[NH:8][c:9]1[n:10][c:11]2[c:12]([cH:13][c:14]([CH2:15][n:16]3[cH:17][n:18][c:19]([Br:20])[cH:21]3)[cH:22][cH:23]2)[s:24]1\"},\"mapped_reaction_smiles\":\"CS(=O)[c:9]1[n:10][c:11]2[c:12]([cH:13][c:14]([CH2:15][n:16]3[cH:17][n:18][c:19]([Br:20])[cH:21]3)[cH:22][cH:23]2)[s:24]1.[OH:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]1[NH2:8]>CC(=O)N(C)C.CCN(C(C)C)C(C)C.O>[OH:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]1[NH:8][c:9]1[n:10][c:11]2[c:12]([cH:13][c:14]([CH2:15][n:16]3[cH:17][n:18][c:19]([Br:20])[cH:21]3)[cH:22][cH:23]2)[s:24]1\"}",
"reactionStep": {
"id": "sa_ced84e7c29fed7783c2e43d6",
"reactionHash": "2ccd857dd05eca6036566cdd54145bb8bde2763b2b88683ab9ec6cacf079705f"
},
"children": [
{
"id": "8363",
"routeId": "sa_302d7b1ce2922e7809872e57",
"moleculeId": "sa_c9044f1a57c9a37b303a443d",
"parentId": "8362",
"isLeaf": true,
"molecule": {
"id": "sa_c9044f1a57c9a37b303a443d",
"inchikey": "PQMCFTMVQORYJC-PHDIDXHHSA-N",
"smiles": "N[C@@H]1CCCC[C@H]1O"
},
"smiles": "N[C@@H]1CCCC[C@H]1O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "8364",
"routeId": "sa_302d7b1ce2922e7809872e57",
"moleculeId": "sa_aa07314745cb29916851bb09",
"parentId": "8362",
"isLeaf": false,
"molecule": {
"id": "sa_aa07314745cb29916851bb09",
"inchikey": "QYUJDKDQBMYTOS-UHFFFAOYSA-N",
"smiles": "CS(=O)c1nc2ccc(Cn3cnc(Br)c3)cc2s1"
},
"smiles": "CS(=O)c1nc2ccc(Cn3cnc(Br)c3)cc2s1",
"reactionStepId": "sa_e8a221b6e51737e2489a65e7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150196566A1;2185;1721428\",\"rsmi\":\"O=C(O[OH:3])c1cccc(Cl)c1.[CH3:1][S:2][c:4]1[n:5][c:6]2[c:7]([cH:8][c:9]([CH2:10][n:11]3[cH:12][n:13][c:14]([Br:15])[cH:16]3)[cH:17][cH:18]2)[s:19]1>ClCCl.O=C(O)O.[Na+]>[CH3:1][S:2](=[O:3])[c:4]1[n:5][c:6]2[c:7]([cH:8][c:9]([CH2:10][n:11]3[cH:12][n:13][c:14]([Br:15])[cH:16]3)[cH:17][cH:18]2)[s:19]1\"},\"mapped_reaction_smiles\":\"O=C(O[OH:3])c1cccc(Cl)c1.[CH3:1][S:2][c:4]1[n:5][c:6]2[c:7]([cH:8][c:9]([CH2:10][n:11]3[cH:12][n:13][c:14]([Br:15])[cH:16]3)[cH:17][cH:18]2)[s:19]1>ClCCl.O=C(O)O.[Na+]>[CH3:1][S:2](=[O:3])[c:4]1[n:5][c:6]2[c:7]([cH:8][c:9]([CH2:10][n:11]3[cH:12][n:13][c:14]([Br:15])[cH:16]3)[cH:17][cH:18]2)[s:19]1\"}",
"reactionStep": {
"id": "sa_e8a221b6e51737e2489a65e7",
"reactionHash": "78fae43803caf87af0b11572ec5b343f113e74c15c82ab9bff4452a944352805"
},
"children": [
{
"id": "8365",
"routeId": "sa_302d7b1ce2922e7809872e57",
"moleculeId": "sa_292aab804b3670e84ce954f3",
"parentId": "8364",
"isLeaf": true,
"molecule": {
"id": "sa_292aab804b3670e84ce954f3",
"inchikey": "NHQDETIJWKXCTC-UHFFFAOYSA-N",
"smiles": "O=C(OO)c1cccc(Cl)c1"
},
"smiles": "O=C(OO)c1cccc(Cl)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "8366",
"routeId": "sa_302d7b1ce2922e7809872e57",
"moleculeId": "sa_3a27d6598418de21eb4a9935",
"parentId": "8364",
"isLeaf": false,
"molecule": {
"id": "sa_3a27d6598418de21eb4a9935",
"inchikey": "PVTOLZXFUQBNGZ-UHFFFAOYSA-N",
"smiles": "CSc1nc2ccc(Cn3cnc(Br)c3)cc2s1"
},
"smiles": "CSc1nc2ccc(Cn3cnc(Br)c3)cc2s1",
"reactionStepId": "sa_8ad539878f92a576c0544d51",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150196566A1;2184;1721427\",\"rsmi\":\"Cl[CH2:9][c:8]1[cH:7][c:6]2[c:5]([n:4][c:3]([S:2][CH3:1])[s:18]2)[cH:17][cH:16]1.[nH:10]1[cH:11][n:12][c:13]([Br:14])[cH:15]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][S:2][c:3]1[n:4][c:5]2[c:6]([cH:7][c:8]([CH2:9][n:10]3[cH:11][n:12][c:13]([Br:14])[cH:15]3)[cH:16][cH:17]2)[s:18]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:9][c:8]1[cH:7][c:6]2[c:5]([n:4][c:3]([S:2][CH3:1])[s:18]2)[cH:17][cH:16]1.[nH:10]1[cH:11][n:12][c:13]([Br:14])[cH:15]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][S:2][c:3]1[n:4][c:5]2[c:6]([cH:7][c:8]([CH2:9][n:10]3[cH:11][n:12][c:13]([Br:14])[cH:15]3)[cH:16][cH:17]2)[s:18]1\"}",
"reactionStep": {
"id": "sa_8ad539878f92a576c0544d51",
"reactionHash": "17731458c764afceb1d88cc67d915efe76796816a555bf37f861b6bfb9deb54c"
},
"children": [
{
"id": "8367",
"routeId": "sa_302d7b1ce2922e7809872e57",
"moleculeId": "sa_65f3b2c7862e9b5961919467",
"parentId": "8366",
"isLeaf": true,
"molecule": {
"id": "sa_65f3b2c7862e9b5961919467",
"inchikey": "FHZALEJIENDROK-UHFFFAOYSA-N",
"smiles": "Brc1cnc[nH]1"
},
"smiles": "Brc1c[nH]cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "8368",
"routeId": "sa_302d7b1ce2922e7809872e57",
"moleculeId": "sa_305abde61c7acc456b5df619",
"parentId": "8366",
"isLeaf": false,
"molecule": {
"id": "sa_305abde61c7acc456b5df619",
"inchikey": "SKUIIRDOHFVYAI-UHFFFAOYSA-N",
"smiles": "CSc1nc2ccc(CCl)cc2s1"
},
"smiles": "CSc1nc2ccc(CCl)cc2s1",
"reactionStepId": "sa_c0d25ef01ec3f92747e8a21f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150196566A1;2079;1721394\",\"rsmi\":\"CS(=O)(=O)[Cl:10].O[CH2:9][c:8]1[cH:7][c:6]2[c:5]([n:4][c:3]([S:2][CH3:1])[s:13]2)[cH:12][cH:11]1>CCN(C(C)C)C(C)C.CN(C)C=O.ClCCl>[CH3:1][S:2][c:3]1[n:4][c:5]2[c:6]([cH:7][c:8]([CH2:9][Cl:10])[cH:11][cH:12]2)[s:13]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)[Cl:10].O[CH2:9][c:8]1[cH:7][c:6]2[c:5]([n:4][c:3]([S:2][CH3:1])[s:13]2)[cH:12][cH:11]1>CCN(C(C)C)C(C)C.CN(C)C=O.ClCCl>[CH3:1][S:2][c:3]1[n:4][c:5]2[c:6]([cH:7][c:8]([CH2:9][Cl:10])[cH:11][cH:12]2)[s:13]1\"}",
"reactionStep": {
"id": "sa_c0d25ef01ec3f92747e8a21f",
"reactionHash": "6ef6d3841be798da921d352e8e71d66f70953dbc061751d6eb70617ab0962111"
},
"children": [
{
"id": "8369",
"routeId": "sa_302d7b1ce2922e7809872e57",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "8368",
"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,
"reactionStep": null,
"children": []
},
{
"id": "8370",
"routeId": "sa_302d7b1ce2922e7809872e57",
"moleculeId": "sa_320dd962e371b319a6c119b4",
"parentId": "8368",
"isLeaf": false,
"molecule": {
"id": "sa_320dd962e371b319a6c119b4",
"inchikey": "USGSPSIAKQRWMQ-UHFFFAOYSA-N",
"smiles": "CSc1nc2ccc(CO)cc2s1"
},
"smiles": "CSc1nc2ccc(CO)cc2s1",
"reactionStepId": "sa_72cb697874594ebd1ebb0558",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150196566A1;2182;1721425\",\"rsmi\":\"CCO[C:9]([c:8]1[cH:7][c:6]2[c:5]([n:4][c:3]([S:2][CH3:1])[s:13]2)[cH:12][cH:11]1)=[O:10]>CC(C)C[Al+]CC(C)C.ClCCl.O=C(O)C(O)C(O)C(=O)O.[HH].[K+].[Na+]>[CH3:1][S:2][c:3]1[n:4][c:5]2[c:6]([cH:7][c:8]([CH2:9][OH:10])[cH:11][cH:12]2)[s:13]1\"},\"mapped_reaction_smiles\":\"CCO[C:9]([c:8]1[cH:7][c:6]2[c:5]([n:4][c:3]([S:2][CH3:1])[s:13]2)[cH:12][cH:11]1)=[O:10]>CC(C)C[Al+]CC(C)C.ClCCl.O=C(O)C(O)C(O)C(=O)O.[HH].[K+].[Na+]>[CH3:1][S:2][c:3]1[n:4][c:5]2[c:6]([cH:7][c:8]([CH2:9][OH:10])[cH:11][cH:12]2)[s:13]1\"}",
"reactionStep": {
"id": "sa_72cb697874594ebd1ebb0558",
"reactionHash": "f4474ef4165fdae64b7fe406b8447c97e54df08e2d0711b47522d87fb763682e"
},
"children": [
{
"id": "8371",
"routeId": "sa_302d7b1ce2922e7809872e57",
"moleculeId": "sa_ade9e4909ad13ee10c350922",
"parentId": "8370",
"isLeaf": false,
"molecule": {
"id": "sa_ade9e4909ad13ee10c350922",
"inchikey": "WYZIXGHANFYHSQ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ccc2nc(SC)sc2c1"
},
"smiles": "CCOC(=O)c1ccc2nc(SC)sc2c1",
"reactionStepId": "sa_e6c7dceb415ee5c873e9486f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150196566A1;2077;1721393\",\"rsmi\":\"Br[c:13]1[n:12][c:9]2[c:8]([cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11][cH:10]2)[s:16]1.[SH:14][CH3:15]>C1CCOC1.CCOCC.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([cH:10][cH:11]1)[n:12][c:13]([S:14][CH3:15])[s:16]2\"},\"mapped_reaction_smiles\":\"Br[c:13]1[n:12][c:9]2[c:8]([cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11][cH:10]2)[s:16]1.[SH:14][CH3:15]>C1CCOC1.CCOCC.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([cH:10][cH:11]1)[n:12][c:13]([S:14][CH3:15])[s:16]2\"}",
"reactionStep": {
"id": "sa_e6c7dceb415ee5c873e9486f",
"reactionHash": "b4c2a6c35ac3973c8ec402a166c2d193b378a4e3a35a24d98f5d070037823caf"
},
"children": [
{
"id": "8372",
"routeId": "sa_302d7b1ce2922e7809872e57",
"moleculeId": "sa_72481999bad040696a9579c1",
"parentId": "8371",
"isLeaf": true,
"molecule": {
"id": "sa_72481999bad040696a9579c1",
"inchikey": "JQZQKEZCRZNJPC-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ccc2nc(Br)sc2c1"
},
"smiles": "CCOC(=O)c1ccc2nc(Br)sc2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "8373",
"routeId": "sa_302d7b1ce2922e7809872e57",
"moleculeId": "sa_4ff6ad4ca1f9c12687e811c2",
"parentId": "8371",
"isLeaf": true,
"molecule": {
"id": "sa_4ff6ad4ca1f9c12687e811c2",
"inchikey": "LSDPWZHWYPCBBB-UHFFFAOYSA-N",
"smiles": "CS"
},
"smiles": "CS",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
]
}
]
}
}