Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CS(=O)(=O)Oc1ccc2ncc(OCCN3CCC(NC(=O)c4ccc5c(c4)NC(=O)CS5)CC3)nc2c1
InChiKey
HTKSCMZSFVFHFN-UHFFFAOYSA-N
Route Signature
28d631640a54b9c32d0498d96fc79ed2e3e43fa841ef4aaa13d7ab7f78002942
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_cda4ead1787487832262e787",
"signature": "28d631640a54b9c32d0498d96fc79ed2e3e43fa841ef4aaa13d7ab7f78002942",
"contentHash": "9f1b804697b8f040bfd514da52675a1fe5582e63b566e46fc9a8bc86f798d95f",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_b08dc015d0957cb482e47aff",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00367",
"moleculeId": "sa_c92188453ac886ca5ba85c70",
"smiles": "CS(=O)(=O)Oc1ccc2ncc(OCCN3CCC(NC(=O)c4ccc5c(c4)NC(=O)CS5)CC3)nc2c1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_c92188453ac886ca5ba85c70",
"inchikey": "HTKSCMZSFVFHFN-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Oc1ccc2ncc(OCCN3CCC(NC(=O)c4ccc5c(c4)NC(=O)CS5)CC3)nc2c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "4132",
"routeId": "sa_cda4ead1787487832262e787",
"moleculeId": "sa_c92188453ac886ca5ba85c70",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c92188453ac886ca5ba85c70",
"inchikey": "HTKSCMZSFVFHFN-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Oc1ccc2ncc(OCCN3CCC(NC(=O)c4ccc5c(c4)NC(=O)CS5)CC3)nc2c1"
},
"smiles": "CS(=O)(=O)Oc1ccc2ncc(OCCN3CCC(NC(=O)c4ccc5c(c4)NC(=O)CS5)CC3)nc2c1",
"reactionStepId": "sa_779b1966df49aefadfb6e31a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927542B2;0477;1562599\",\"rsmi\":\"CS(=O)(=O)O[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][c:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][c:12]([O:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][CH:19]([NH:20][C:21](=[O:22])[c:23]4[cH:24][c:25]5[c:26]([cH:27][cH:28]4)[S:29][CH2:30][C:31](=[O:32])[NH:33]5)[CH2:34][CH2:35]3)[n:36][c:37]2[cH:38]1>CCN(CC)CC.CN(C)C=O>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][c:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][c:12]([O:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][CH:19]([NH:20][C:21](=[O:22])[c:23]4[cH:24][c:25]5[c:26]([cH:27][cH:28]4)[S:29][CH2:30][C:31](=[O:32])[NH:33]5)[CH2:34][CH2:35]3)[n:36][c:37]2[cH:38]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][c:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][c:12]([O:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][CH:19]([NH:20][C:21](=[O:22])[c:23]4[cH:24][c:25]5[c:26]([cH:27][cH:28]4)[S:29][CH2:30][C:31](=[O:32])[NH:33]5)[CH2:34][CH2:35]3)[n:36][c:37]2[cH:38]1>CCN(CC)CC.CN(C)C=O>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][c:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][c:12]([O:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][CH:19]([NH:20][C:21](=[O:22])[c:23]4[cH:24][c:25]5[c:26]([cH:27][cH:28]4)[S:29][CH2:30][C:31](=[O:32])[NH:33]5)[CH2:34][CH2:35]3)[n:36][c:37]2[cH:38]1\"}",
"reactionStep": {
"id": "sa_779b1966df49aefadfb6e31a",
"reactionHash": "a6d7f0befc5eea162c6ad0fe1dedf289da9d3c70e005a420aa2411118a34c659"
},
"children": [
{
"id": "4133",
"routeId": "sa_cda4ead1787487832262e787",
"moleculeId": "sa_988907ae0e75bf24e80236f2",
"parentId": "4132",
"isLeaf": false,
"molecule": {
"id": "sa_988907ae0e75bf24e80236f2",
"inchikey": "IGFNTLISFMYDOY-UHFFFAOYSA-N",
"smiles": "O=C1CSc2ccc(C(=O)NC3CCN(CCOc4cnc5ccc(O)cc5n4)CC3)cc2N1"
},
"smiles": "O=C1CSc2ccc(C(=O)NC3CCN(CCOc4cnc5ccc(O)cc5n4)CC3)cc2N1",
"reactionStepId": "sa_0385fb4433eb3ff67cd9859f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927542B2;0469;1562596\",\"rsmi\":\"C[O:24][c:23]1[cH:22][c:21]2[n:20][c:19]([O:18][CH2:17][CH2:16][N:15]3[CH2:14][CH2:13][CH:12]([NH:11][C:9]([c:8]4[cH:7][c:6]5[c:5]([cH:33][cH:32]4)[S:4][CH2:3][C:2](=[O:1])[NH:34]5)=[O:10])[CH2:31][CH2:30]3)[cH:29][n:28][c:27]2[cH:26][cH:25]1>BrB(Br)Br.CO.ClCCl>[O:1]=[C:2]1[CH2:3][S:4][c:5]2[c:6]([cH:7][c:8]([C:9](=[O:10])[NH:11][CH:12]3[CH2:13][CH2:14][N:15]([CH2:16][CH2:17][O:18][c:19]4[n:20][c:21]5[cH:22][c:23]([OH:24])[cH:25][cH:26][c:27]5[n:28][cH:29]4)[CH2:30][CH2:31]3)[cH:32][cH:33]2)[NH:34]1\"},\"mapped_reaction_smiles\":\"C[O:24][c:23]1[cH:22][c:21]2[n:20][c:19]([O:18][CH2:17][CH2:16][N:15]3[CH2:14][CH2:13][CH:12]([NH:11][C:9]([c:8]4[cH:7][c:6]5[c:5]([cH:33][cH:32]4)[S:4][CH2:3][C:2](=[O:1])[NH:34]5)=[O:10])[CH2:31][CH2:30]3)[cH:29][n:28][c:27]2[cH:26][cH:25]1>BrB(Br)Br.CO.ClCCl>[O:1]=[C:2]1[CH2:3][S:4][c:5]2[c:6]([cH:7][c:8]([C:9](=[O:10])[NH:11][CH:12]3[CH2:13][CH2:14][N:15]([CH2:16][CH2:17][O:18][c:19]4[n:20][c:21]5[cH:22][c:23]([OH:24])[cH:25][cH:26][c:27]5[n:28][cH:29]4)[CH2:30][CH2:31]3)[cH:32][cH:33]2)[NH:34]1\"}",
"reactionStep": {
"id": "sa_0385fb4433eb3ff67cd9859f",
"reactionHash": "6bf28e58dae9056f1256528682600e3eba6b527bd11b5da4c90990e0df643466"
},
"children": [
{
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"routeId": "sa_cda4ead1787487832262e787",
"moleculeId": "sa_d0186116a056c60ec6310d78",
"parentId": "4133",
"isLeaf": false,
"molecule": {
"id": "sa_d0186116a056c60ec6310d78",
"inchikey": "SCWIFTGSFCMJAN-UHFFFAOYSA-N",
"smiles": "COc1ccc2ncc(OCCN3CCC(NC(=O)c4ccc5c(c4)NC(=O)CS5)CC3)nc2c1"
},
"smiles": "COc1ccc2ncc(OCCN3CCC(NC(=O)c4ccc5c(c4)NC(=O)CS5)CC3)nc2c1",
"reactionStepId": "sa_d7c410a2a7e18b9a050defd5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927542B2;0178;1562501\",\"rsmi\":\"O[C:18](=[O:19])[c:20]1[cH:21][c:22]2[c:23]([cH:24][cH:25]1)[S:26][CH2:27][C:28](=[O:29])[NH:30]2.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([O:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH:16]([NH2:17])[CH2:31][CH2:32]3)[n:33][c:34]2[cH:35]1>CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.On1nnc2ccccc21>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([O:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH:16]([NH:17][C:18](=[O:19])[c:20]4[cH:21][c:22]5[c:23]([cH:24][cH:25]4)[S:26][CH2:27][C:28](=[O:29])[NH:30]5)[CH2:31][CH2:32]3)[n:33][c:34]2[cH:35]1\"},\"mapped_reaction_smiles\":\"O[C:18](=[O:19])[c:20]1[cH:21][c:22]2[c:23]([cH:24][cH:25]1)[S:26][CH2:27][C:28](=[O:29])[NH:30]2.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([O:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH:16]([NH2:17])[CH2:31][CH2:32]3)[n:33][c:34]2[cH:35]1>CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.On1nnc2ccccc21>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([O:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH:16]([NH:17][C:18](=[O:19])[c:20]4[cH:21][c:22]5[c:23]([cH:24][cH:25]4)[S:26][CH2:27][C:28](=[O:29])[NH:30]5)[CH2:31][CH2:32]3)[n:33][c:34]2[cH:35]1\"}",
"reactionStep": {
"id": "sa_d7c410a2a7e18b9a050defd5",
"reactionHash": "71c83077ab6fd4a1a08243700416d1f7f47cfffbfe9764df442be45962e14e59"
},
"children": [
{
"id": "4135",
"routeId": "sa_cda4ead1787487832262e787",
"moleculeId": "sa_5f10df07cb0f6c366bb2d42c",
"parentId": "4134",
"isLeaf": false,
"molecule": {
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"inchikey": "FOIZIUWGSCZTMR-UHFFFAOYSA-N",
"smiles": "COc1ccc2ncc(OCCN3CCC(N)CC3)nc2c1"
},
"smiles": "COc1ccc2ncc(OCCN3CCC(N)CC3)nc2c1",
"reactionStepId": "sa_e6c913fcbb662696e1e815d4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927542B2;0175;1562500\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:17][CH:16]1[CH2:15][CH2:14][N:13]([CH2:12][CH2:11][O:10][c:9]2[cH:8][n:7][c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22][c:21]3[n:20]2)[CH2:19][CH2:18]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([O:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH:16]([NH2:17])[CH2:18][CH2:19]3)[n:20][c:21]2[cH:22]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:17][CH:16]1[CH2:15][CH2:14][N:13]([CH2:12][CH2:11][O:10][c:9]2[cH:8][n:7][c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22][c:21]3[n:20]2)[CH2:19][CH2:18]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([O:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH:16]([NH2:17])[CH2:18][CH2:19]3)[n:20][c:21]2[cH:22]1\"}",
"reactionStep": {
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"reactionHash": "d3869375c5ca6c55088ce004743177e19d98cb9a0143e8708905a45e072cf367"
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"children": [
{
"id": "4136",
"routeId": "sa_cda4ead1787487832262e787",
"moleculeId": "sa_cfd3570a659d200b6bb3cd08",
"parentId": "4135",
"isLeaf": false,
"molecule": {
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"inchikey": "NAVQHOSTMJFHIA-UHFFFAOYSA-N",
"smiles": "COc1ccc2ncc(OCCN3CCC(NC(=O)OC(C)(C)C)CC3)nc2c1"
},
"smiles": "COc1ccc2ncc(OCCN3CCC(NC(=O)OC(C)(C)C)CC3)nc2c1",
"reactionStepId": "sa_6dfd285cb1fb4135f81177b8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927542B2;0172;1562499\",\"rsmi\":\"Cl[c:9]1[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:29][c:28]2[n:27]1.[OH:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]1>CN(C)C=O.[HH].[Na+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([O:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]3)[n:27][c:28]2[cH:29]1\"},\"mapped_reaction_smiles\":\"Cl[c:9]1[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:29][c:28]2[n:27]1.[OH:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]1>CN(C)C=O.[HH].[Na+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([O:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]3)[n:27][c:28]2[cH:29]1\"}",
"reactionStep": {
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"children": [
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"moleculeId": "sa_fc3cbb1a03e2ff4c74835230",
"parentId": "4136",
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"molecule": {
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"inchikey": "DDAYUMXPDZXTIO-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NC1CCN(CCO)CC1"
},
"smiles": "CC(C)(C)OC(=O)NC1CCN(CCO)CC1",
"reactionStepId": "sa_cccac3439f2bf9972dd1566b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927542B2;0169;1562498\",\"rsmi\":\"Br[CH2:13][CH2:14][OH:15].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][NH:12][CH2:16][CH2:17]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:13][CH2:14][OH:15])[CH2:16][CH2:17]1\"},\"mapped_reaction_smiles\":\"Br[CH2:13][CH2:14][OH:15].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][NH:12][CH2:16][CH2:17]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:13][CH2:14][OH:15])[CH2:16][CH2:17]1\"}",
"reactionStep": {
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"smiles": "CC(C)(C)OC(O)=NC1CCNCC1"
},
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{
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"molecule": {
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"smiles": "OCCBr"
},
"smiles": "OCCBr",
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}
]
},
{
"id": "4140",
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"molecule": {
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"inchikey": "WJDJKCAURKUNNC-UHFFFAOYSA-N",
"smiles": "COc1ccc2ncc(Cl)nc2c1"
},
"smiles": "COc1ccc2ncc(Cl)nc2c1",
"reactionStepId": null,
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}
]
}
]
},
{
"id": "4141",
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"molecule": {
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"inchikey": "NBIVLYUEDPRLGI-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ccc2c(c1)N=C(O)CS2"
},
"smiles": "O=C1CSc2ccc(C(=O)O)cc2N1",
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}
]
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]
},
{
"id": "4142",
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"moleculeId": "sa_5e0dc186fcc91346e0537475",
"parentId": "4132",
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"molecule": {
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"inchikey": "IZDROVVXIHRYMH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)OS(C)(=O)=O"
},
"smiles": "CS(=O)(=O)OS(C)(=O)=O",
"reactionStepId": null,
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}
]
}
}