Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCCNc1nc(Nc2ccc(C(N)=O)cc2)ncc1C(=O)NCCCNC(=O)OC(C)(C)C
InChiKey
FGVZRAGLQXUPQJ-UHFFFAOYSA-N
Route Signature
39582a83509e15be9edae6b79d4143d037f620a85f62c1bf43ab19424cb928ea
Synthesis route with 4 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_dd057c15a30118cba0f36e3a",
"signature": "39582a83509e15be9edae6b79d4143d037f620a85f62c1bf43ab19424cb928ea",
"contentHash": "0469043e7af51f7a58308a3a088dcba41406d548dbac34e52f64082286789bdd",
"length": 4,
"isConvergent": false
},
"target": {
"id": "sa_1841337eed62787fe1dff50f",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-06989",
"moleculeId": "sa_646f0f85b97f558d1815bb2e",
"smiles": "CCCNc1nc(Nc2ccc(C(N)=O)cc2)ncc1C(=O)NCCCNC(=O)OC(C)(C)C",
"routeLength": 4,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_646f0f85b97f558d1815bb2e",
"inchikey": "FGVZRAGLQXUPQJ-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Nc2ccc(C(N)=O)cc2)ncc1C(=O)NCCCNC(=O)OC(C)(C)C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "16066",
"routeId": "sa_dd057c15a30118cba0f36e3a",
"moleculeId": "sa_646f0f85b97f558d1815bb2e",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_646f0f85b97f558d1815bb2e",
"inchikey": "FGVZRAGLQXUPQJ-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Nc2ccc(C(N)=O)cc2)ncc1C(=O)NCCCNC(=O)OC(C)(C)C"
},
"smiles": "CCCNc1nc(Nc2ccc(C(N)=O)cc2)ncc1C(=O)NCCCNC(=O)OC(C)(C)C",
"reactionStepId": "sa_5ef1785095ed3d8abe335977",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150045339A1;0869;1652916\",\"rsmi\":\"O[OH:15].[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:16][cH:17]2)[n:18][cH:19][c:20]1[C:21](=[O:22])[NH:23][CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34]>CCO.CS(C)=O.O.[Na+].O>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]([NH2:14])=[O:15])[cH:16][cH:17]2)[n:18][cH:19][c:20]1[C:21](=[O:22])[NH:23][CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34]\"},\"mapped_reaction_smiles\":\"O[OH:15].[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:16][cH:17]2)[n:18][cH:19][c:20]1[C:21](=[O:22])[NH:23][CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34]>CCO.CS(C)=O.O.[Na+].O>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]([NH2:14])=[O:15])[cH:16][cH:17]2)[n:18][cH:19][c:20]1[C:21](=[O:22])[NH:23][CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34]\"}",
"reactionStep": {
"id": "sa_5ef1785095ed3d8abe335977",
"reactionHash": "bd991e7c5d35a33fae8eeb4042b3b0c0c9573a3b30ecb3c0e853134323512f52"
},
"children": [
{
"id": "16067",
"routeId": "sa_dd057c15a30118cba0f36e3a",
"moleculeId": "sa_4dba68d938224067da688ab5",
"parentId": "16066",
"isLeaf": true,
"molecule": {
"id": "sa_4dba68d938224067da688ab5",
"inchikey": "MHAJPDPJQMAIIY-UHFFFAOYSA-N",
"smiles": "OO"
},
"smiles": "OO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "16068",
"routeId": "sa_dd057c15a30118cba0f36e3a",
"moleculeId": "sa_8a18ba9bc0d945afdee6cdf8",
"parentId": "16066",
"isLeaf": false,
"molecule": {
"id": "sa_8a18ba9bc0d945afdee6cdf8",
"inchikey": "XNCHCWDOCJKUTM-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C(=O)NCCCNC(=O)OC(C)(C)C"
},
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C(=O)NCCCNC(=O)OC(C)(C)C",
"reactionStepId": "sa_39cb970b0c93619f06f24107",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150045339A1;0867;1652915\",\"rsmi\":\"O[C:20]([c:19]1[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18]1)=[O:21].[NH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33]>CCN(CC)CC.CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.Cl.O.O=C(O)O.On1nnc2ccccc21.[Na+]>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20](=[O:21])[NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33]\"},\"mapped_reaction_smiles\":\"O[C:20]([c:19]1[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18]1)=[O:21].[NH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33]>CCN(CC)CC.CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.Cl.O.O=C(O)O.On1nnc2ccccc21.[Na+]>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20](=[O:21])[NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33]\"}",
"reactionStep": {
"id": "sa_39cb970b0c93619f06f24107",
"reactionHash": "a09216127554b21fed2dbc3aaaecdbec6d693d6ac2980df8e856052a12fbb025"
},
"children": [
{
"id": "16069",
"routeId": "sa_dd057c15a30118cba0f36e3a",
"moleculeId": "sa_b7baf0d19ca5efe170e09801",
"parentId": "16068",
"isLeaf": false,
"molecule": {
"id": "sa_b7baf0d19ca5efe170e09801",
"inchikey": "KITLYJXMPHTPKS-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C(=O)O"
},
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C(=O)O",
"reactionStepId": "sa_2d3c6ce21d0bc3c2a2231d01",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150045339A1;0732;1652876\",\"rsmi\":\"CC[O:22][C:20]([c:19]1[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18]1)=[O:21]>C1CCOC1.CCO.Cl.[Na+].O>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20](=[O:21])[OH:22]\"},\"mapped_reaction_smiles\":\"CC[O:22][C:20]([c:19]1[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18]1)=[O:21]>C1CCOC1.CCO.Cl.[Na+].O>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20](=[O:21])[OH:22]\"}",
"reactionStep": {
"id": "sa_2d3c6ce21d0bc3c2a2231d01",
"reactionHash": "837bbf1408f6eeefe8512566dbfceb9f9e8b31d2091e53e0089b15699c842947"
},
"children": [
{
"id": "16070",
"routeId": "sa_dd057c15a30118cba0f36e3a",
"moleculeId": "sa_4998940f267de0ed7835c51f",
"parentId": "16069",
"isLeaf": false,
"molecule": {
"id": "sa_4998940f267de0ed7835c51f",
"inchikey": "KIJRYBQBTGOVDP-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C(=O)OCC"
},
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C(=O)OCC",
"reactionStepId": "sa_d05d85ecba2c6a24ba848cc2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150045339A1;0729;1652875\",\"rsmi\":\"Br[c:9]1[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]1.[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH2:8])[n:17][cH:18][c:19]1[C:20](=[O:21])[O:22][CH2:23][CH3:24]>C1COCCO1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd]>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20](=[O:21])[O:22][CH2:23][CH3:24]\"},\"mapped_reaction_smiles\":\"Br[c:9]1[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]1.[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH2:8])[n:17][cH:18][c:19]1[C:20](=[O:21])[O:22][CH2:23][CH3:24]>C1COCCO1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd]>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20](=[O:21])[O:22][CH2:23][CH3:24]\"}",
"reactionStep": {
"id": "sa_d05d85ecba2c6a24ba848cc2",
"reactionHash": "09f6222917881d02ad8152f4ca02dca41b248eb0a7b970ae4f46e143b109ad60"
},
"children": [
{
"id": "16071",
"routeId": "sa_dd057c15a30118cba0f36e3a",
"moleculeId": "sa_e82e54e2a01f1850fcd85b29",
"parentId": "16070",
"isLeaf": true,
"molecule": {
"id": "sa_e82e54e2a01f1850fcd85b29",
"inchikey": "HQSCPPCMBMFJJN-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(Br)cc1"
},
"smiles": "N#Cc1ccc(Br)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "16072",
"routeId": "sa_dd057c15a30118cba0f36e3a",
"moleculeId": "sa_7c3222c0826d903b7e522422",
"parentId": "16070",
"isLeaf": true,
"molecule": {
"id": "sa_7c3222c0826d903b7e522422",
"inchikey": "IQPBEDDGJHFQML-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(N)ncc1C(=O)OCC"
},
"smiles": "CCCNc1nc(N)ncc1C(=O)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "16073",
"routeId": "sa_dd057c15a30118cba0f36e3a",
"moleculeId": "sa_cd84632e4c6b7a4883dca4d7",
"parentId": "16068",
"isLeaf": true,
"molecule": {
"id": "sa_cd84632e4c6b7a4883dca4d7",
"inchikey": "POHWAQLZBIMPRN-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(O)=NCCCN"
},
"smiles": "CC(C)(C)OC(=O)NCCCN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}