Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CS(=O)(=O)O[C@@H]1CCCC[C@H]1Nc1nc2ccc(Cn3cnc4cccnc43)cc2s1
InChiKey
LFJZUUMJUJKNBO-CRAIPNDOSA-N
Route Signature
186eb4a9fed972ebc445f2efa916ebae227fa318a1574f8fc6fcb8e838aff759
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_f90a2bab055d0a20c288ef66",
"signature": "186eb4a9fed972ebc445f2efa916ebae227fa318a1574f8fc6fcb8e838aff759",
"contentHash": "ec524e1278e86e8db9f45303e6fbccaabe23a164db3b3b336672a9b008204b70",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_0e2a928227218b182da5f5d1",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00105",
"moleculeId": "sa_41d72fc6d11e25e5d5667109",
"smiles": "CS(=O)(=O)O[C@@H]1CCCC[C@H]1Nc1nc2ccc(Cn3cnc4cccnc43)cc2s1",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_41d72fc6d11e25e5d5667109",
"inchikey": "LFJZUUMJUJKNBO-CRAIPNDOSA-N",
"smiles": "CS(=O)(=O)O[C@@H]1CCCC[C@H]1Nc1nc2ccc(Cn3cnc4cccnc43)cc2s1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12426",
"routeId": "sa_f90a2bab055d0a20c288ef66",
"moleculeId": "sa_41d72fc6d11e25e5d5667109",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_41d72fc6d11e25e5d5667109",
"inchikey": "LFJZUUMJUJKNBO-CRAIPNDOSA-N",
"smiles": "CS(=O)(=O)O[C@@H]1CCCC[C@H]1Nc1nc2ccc(Cn3cnc4cccnc43)cc2s1"
},
"smiles": "CS(=O)(=O)O[C@@H]1CCCC[C@H]1Nc1nc2ccc(Cn3cnc4cccnc43)cc2s1",
"reactionStepId": "sa_34f61806af7b6de34fb8682f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130096113A1;2085;1355888\",\"rsmi\":\"O[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][C@@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]1[NH:12][c:13]1[n:14][c:15]2[c:16]([cH:17][c:18]([CH2:19][n:20]3[cH:21][n:22][c:23]4[cH:24][cH:25][cH:26][n:27][c:28]34)[cH:29][cH:30]2)[s:31]1>CCO>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][C@@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]1[NH:12][c:13]1[n:14][c:15]2[c:16]([cH:17][c:18]([CH2:19][n:20]3[cH:21][n:22][c:23]4[cH:24][cH:25][cH:26][n:27][c:28]34)[cH:29][cH:30]2)[s:31]1\"},\"mapped_reaction_smiles\":\"O[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][C@@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]1[NH:12][c:13]1[n:14][c:15]2[c:16]([cH:17][c:18]([CH2:19][n:20]3[cH:21][n:22][c:23]4[cH:24][cH:25][cH:26][n:27][c:28]34)[cH:29][cH:30]2)[s:31]1>CCO>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][C@@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]1[NH:12][c:13]1[n:14][c:15]2[c:16]([cH:17][c:18]([CH2:19][n:20]3[cH:21][n:22][c:23]4[cH:24][cH:25][cH:26][n:27][c:28]34)[cH:29][cH:30]2)[s:31]1\"}",
"reactionStep": {
"id": "sa_34f61806af7b6de34fb8682f",
"reactionHash": "7fd5ecb3b6509419a58841a31805a9c758da2ab898b6f645d81c2ea0d952f36b"
},
"children": [
{
"id": "12427",
"routeId": "sa_f90a2bab055d0a20c288ef66",
"moleculeId": "sa_72b5c17d52f0a808407f222a",
"parentId": "12426",
"isLeaf": true,
"molecule": {
"id": "sa_72b5c17d52f0a808407f222a",
"inchikey": "AFVFQIVMOAPDHO-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)O"
},
"smiles": "CS(=O)(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12428",
"routeId": "sa_f90a2bab055d0a20c288ef66",
"moleculeId": "sa_a246ca15990854df21f4d981",
"parentId": "12426",
"isLeaf": false,
"molecule": {
"id": "sa_a246ca15990854df21f4d981",
"inchikey": "UPBQACCGDZGCBR-RHSMWYFYSA-N",
"smiles": "O[C@@H]1CCCC[C@H]1Nc1nc2ccc(Cn3cnc4cccnc43)cc2s1"
},
"smiles": "O[C@@H]1CCCC[C@H]1Nc1nc2ccc(Cn3cnc4cccnc43)cc2s1",
"reactionStepId": "sa_43aeb8fd222857ae98b25afd",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130096113A1;2084;1355887\",\"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]4[cH:20][cH:21][cH:22][n:23][c:24]34)[cH:25][cH:26]2)[s:27]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.CCOC(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]4[cH:20][cH:21][cH:22][n:23][c:24]34)[cH:25][cH:26]2)[s:27]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]4[cH:20][cH:21][cH:22][n:23][c:24]34)[cH:25][cH:26]2)[s:27]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.CCOC(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]4[cH:20][cH:21][cH:22][n:23][c:24]34)[cH:25][cH:26]2)[s:27]1\"}",
"reactionStep": {
"id": "sa_43aeb8fd222857ae98b25afd",
"reactionHash": "a1845d21a6af943b4202ec436a78364daa1736c0fc71e01e8885d3e59e769375"
},
"children": [
{
"id": "12429",
"routeId": "sa_f90a2bab055d0a20c288ef66",
"moleculeId": "sa_c9044f1a57c9a37b303a443d",
"parentId": "12428",
"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": "12430",
"routeId": "sa_f90a2bab055d0a20c288ef66",
"moleculeId": "sa_dbb64ef6eb89706e694d5473",
"parentId": "12428",
"isLeaf": false,
"molecule": {
"id": "sa_dbb64ef6eb89706e694d5473",
"inchikey": "PYEZGZYQLUOGNQ-UHFFFAOYSA-N",
"smiles": "CS(=O)c1nc2ccc(Cn3cnc4cccnc43)cc2s1"
},
"smiles": "CS(=O)c1nc2ccc(Cn3cnc4cccnc43)cc2s1",
"reactionStepId": "sa_47ded9b7426a1ba00b11f6c1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130096113A1;2083;1355886\",\"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]4[cH:15][cH:16][cH:17][n:18][c:19]34)[cH:20][cH:21]2)[s:22]1>ClCCl>[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]4[cH:15][cH:16][cH:17][n:18][c:19]34)[cH:20][cH:21]2)[s:22]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]4[cH:15][cH:16][cH:17][n:18][c:19]34)[cH:20][cH:21]2)[s:22]1>ClCCl>[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]4[cH:15][cH:16][cH:17][n:18][c:19]34)[cH:20][cH:21]2)[s:22]1\"}",
"reactionStep": {
"id": "sa_47ded9b7426a1ba00b11f6c1",
"reactionHash": "a07424387667195f7fc375f9a54acd25fa3d8438b00194a50dcbf2050e3406b5"
},
"children": [
{
"id": "12431",
"routeId": "sa_f90a2bab055d0a20c288ef66",
"moleculeId": "sa_5bc71d9c574423eebae9aa05",
"parentId": "12430",
"isLeaf": false,
"molecule": {
"id": "sa_5bc71d9c574423eebae9aa05",
"inchikey": "KDMGKMVISYJOQE-UHFFFAOYSA-N",
"smiles": "CSc1nc2ccc(Cn3cnc4cccnc43)cc2s1"
},
"smiles": "CSc1nc2ccc(Cn3cnc4cccnc43)cc2s1",
"reactionStepId": "sa_1c21446cc462ce74ae589bed",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130096113A1;2082;1355885\",\"rsmi\":\"Cl[CH2:9][c:8]1[cH:7][c:6]2[c:5]([n:4][c:3]([S:2][CH3:1])[s:21]2)[cH:20][cH:19]1.[nH:10]1[cH:11][n:12][c:13]2[cH:14][cH:15][cH:16][n:17][c:18]12>CN(C)C=O.[HH].[Na+]>[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]4[cH:14][cH:15][cH:16][n:17][c:18]34)[cH:19][cH:20]2)[s:21]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:21]2)[cH:20][cH:19]1.[nH:10]1[cH:11][n:12][c:13]2[cH:14][cH:15][cH:16][n:17][c:18]12>CN(C)C=O.[HH].[Na+]>[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]4[cH:14][cH:15][cH:16][n:17][c:18]34)[cH:19][cH:20]2)[s:21]1\"}",
"reactionStep": {
"id": "sa_1c21446cc462ce74ae589bed",
"reactionHash": "8ba74a3cae638584a4d1d48e08c8b3404f0b8a2fc59774e29533468c44416674"
},
"children": [
{
"id": "12432",
"routeId": "sa_f90a2bab055d0a20c288ef66",
"moleculeId": "sa_aa52d14525717938f63a26f7",
"parentId": "12431",
"isLeaf": true,
"molecule": {
"id": "sa_aa52d14525717938f63a26f7",
"inchikey": "GAMYYCRTACQSBR-UHFFFAOYSA-N",
"smiles": "c1cnc2nc[nH]c2c1"
},
"smiles": "c1cnc2[nH]cnc2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12433",
"routeId": "sa_f90a2bab055d0a20c288ef66",
"moleculeId": "sa_305abde61c7acc456b5df619",
"parentId": "12431",
"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\":\"US20130096113A1;2081;1355884\",\"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": "12434",
"routeId": "sa_f90a2bab055d0a20c288ef66",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "12433",
"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": "12435",
"routeId": "sa_f90a2bab055d0a20c288ef66",
"moleculeId": "sa_320dd962e371b319a6c119b4",
"parentId": "12433",
"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\":\"US20130096113A1;2184;1355916\",\"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": "12436",
"routeId": "sa_f90a2bab055d0a20c288ef66",
"moleculeId": "sa_ade9e4909ad13ee10c350922",
"parentId": "12435",
"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\":\"US20130096113A1;2079;1355883\",\"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": "12437",
"routeId": "sa_f90a2bab055d0a20c288ef66",
"moleculeId": "sa_72481999bad040696a9579c1",
"parentId": "12436",
"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": "12438",
"routeId": "sa_f90a2bab055d0a20c288ef66",
"moleculeId": "sa_4ff6ad4ca1f9c12687e811c2",
"parentId": "12436",
"isLeaf": true,
"molecule": {
"id": "sa_4ff6ad4ca1f9c12687e811c2",
"inchikey": "LSDPWZHWYPCBBB-UHFFFAOYSA-N",
"smiles": "CS"
},
"smiles": "CS",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
},
{
"id": "12439",
"routeId": "sa_f90a2bab055d0a20c288ef66",
"moleculeId": "sa_292aab804b3670e84ce954f3",
"parentId": "12430",
"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": []
}
]
}
]
}
]
}
}