Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(Cc1nc2ccccc2n1CC(=O)NCc1ccccn1)C1CCCc2cccnc21
InChiKey
LTMGFOVCJPWXDE-UHFFFAOYSA-N
Route Signature
7d48b52f6e022b05aa74ce47c0ad06a7f89c05ac186c89ac9c3347e1b4051f93
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_b92556d80f2dbc3a428b2c75",
"signature": "7d48b52f6e022b05aa74ce47c0ad06a7f89c05ac186c89ac9c3347e1b4051f93",
"contentHash": "2010278db4cdc9dfeef2e9bdf55fcdd38f4aa77ed2f7b64e262adcd5774864db",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_f8504db314e24d82dc09b35a",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-02391",
"moleculeId": "sa_23f18f26bad841bb92236a9b",
"smiles": "CN(Cc1nc2ccccc2n1CC(=O)NCc1ccccn1)C1CCCc2cccnc21",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_23f18f26bad841bb92236a9b",
"inchikey": "LTMGFOVCJPWXDE-UHFFFAOYSA-N",
"smiles": "CN(Cc1nc2ccccc2n1CC(=O)NCc1ccccn1)C1CCCc2cccnc21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "6339",
"routeId": "sa_b92556d80f2dbc3a428b2c75",
"moleculeId": "sa_23f18f26bad841bb92236a9b",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_23f18f26bad841bb92236a9b",
"inchikey": "LTMGFOVCJPWXDE-UHFFFAOYSA-N",
"smiles": "CN(Cc1nc2ccccc2n1CC(=O)NCc1ccccn1)C1CCCc2cccnc21"
},
"smiles": "CN(Cc1nc2ccccc2n1CC(=O)NCc1ccccn1)C1CCCc2cccnc21",
"reactionStepId": "sa_e38d84fe747048acb89531be",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080096861A1;0523;565574\",\"rsmi\":\"O[C:14]([CH2:13][n:12]1[c:4]([CH2:3][N:2]([CH3:1])[CH:24]2[CH2:25][CH2:26][CH2:27][c:28]3[c:29]2[n:30][cH:31][cH:32][cH:33]3)[n:5][c:6]2[c:7]1[cH:8][cH:9][cH:10][cH:11]2)=[O:15].[NH2:16][CH2:17][c:18]1[n:19][cH:20][cH:21][cH:22][cH:23]1>CN(Cc1nc2ccccc2n1CC(=O)NCCCNC(=O)OC(C)(C)C)C1CCCc2cccnc21>[CH3:1][N:2]([CH2:3][c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[n:12]1[CH2:13][C:14](=[O:15])[NH:16][CH2:17][c:18]1[n:19][cH:20][cH:21][cH:22][cH:23]1)[CH:24]1[CH2:25][CH2:26][CH2:27][c:28]2[c:29]1[n:30][cH:31][cH:32][cH:33]2\"},\"mapped_reaction_smiles\":\"O[C:14]([CH2:13][n:12]1[c:4]([CH2:3][N:2]([CH3:1])[CH:24]2[CH2:25][CH2:26][CH2:27][c:28]3[c:29]2[n:30][cH:31][cH:32][cH:33]3)[n:5][c:6]2[c:7]1[cH:8][cH:9][cH:10][cH:11]2)=[O:15].[NH2:16][CH2:17][c:18]1[n:19][cH:20][cH:21][cH:22][cH:23]1>CN(Cc1nc2ccccc2n1CC(=O)NCCCNC(=O)OC(C)(C)C)C1CCCc2cccnc21>[CH3:1][N:2]([CH2:3][c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[n:12]1[CH2:13][C:14](=[O:15])[NH:16][CH2:17][c:18]1[n:19][cH:20][cH:21][cH:22][cH:23]1)[CH:24]1[CH2:25][CH2:26][CH2:27][c:28]2[c:29]1[n:30][cH:31][cH:32][cH:33]2\"}",
"reactionStep": {
"id": "sa_e38d84fe747048acb89531be",
"reactionHash": "47644d96063f78cf8a88ab7bc700b03d50127972bec101326d55183ee9fc661b"
},
"children": [
{
"id": "6340",
"routeId": "sa_b92556d80f2dbc3a428b2c75",
"moleculeId": "sa_9f29919bef3a1b0459f6ddc5",
"parentId": "6339",
"isLeaf": false,
"molecule": {
"id": "sa_9f29919bef3a1b0459f6ddc5",
"inchikey": "AAEBEXCYIARFKM-UHFFFAOYSA-N",
"smiles": "CN(Cc1nc2ccccc2n1CC(=O)O)C1CCCc2cccnc21"
},
"smiles": "CN(Cc1nc2ccccc2n1CC(=O)O)C1CCCc2cccnc21",
"reactionStepId": "sa_ca656bd370a55ef66d3c1222",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080096861A1;0513;565567\",\"rsmi\":\"C[O:16][C:14]([CH2:13][n:12]1[c:4]([CH2:3][N:2]([CH3:1])[CH:17]2[CH2:18][CH2:19][CH2:20][c:21]3[c:22]2[n:23][cH:24][cH:25][cH:26]3)[n:5][c:6]2[c:7]1[cH:8][cH:9][cH:10][cH:11]2)=[O:15]>CO.Cl.O.[Li+].O>[CH3:1][N:2]([CH2:3][c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[n:12]1[CH2:13][C:14](=[O:15])[OH:16])[CH:17]1[CH2:18][CH2:19][CH2:20][c:21]2[c:22]1[n:23][cH:24][cH:25][cH:26]2\"},\"mapped_reaction_smiles\":\"C[O:16][C:14]([CH2:13][n:12]1[c:4]([CH2:3][N:2]([CH3:1])[CH:17]2[CH2:18][CH2:19][CH2:20][c:21]3[c:22]2[n:23][cH:24][cH:25][cH:26]3)[n:5][c:6]2[c:7]1[cH:8][cH:9][cH:10][cH:11]2)=[O:15]>CO.Cl.O.[Li+].O>[CH3:1][N:2]([CH2:3][c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[n:12]1[CH2:13][C:14](=[O:15])[OH:16])[CH:17]1[CH2:18][CH2:19][CH2:20][c:21]2[c:22]1[n:23][cH:24][cH:25][cH:26]2\"}",
"reactionStep": {
"id": "sa_ca656bd370a55ef66d3c1222",
"reactionHash": "a08c77be10e76b5457ac8a54bc8406c59bf65b4bc0a557513820acbb6ae046d9"
},
"children": [
{
"id": "6341",
"routeId": "sa_b92556d80f2dbc3a428b2c75",
"moleculeId": "sa_05a619f56110d1dd899224b0",
"parentId": "6340",
"isLeaf": false,
"molecule": {
"id": "sa_05a619f56110d1dd899224b0",
"inchikey": "HDVCVYUAGVNRNY-UHFFFAOYSA-N",
"smiles": "COC(=O)Cn1c(CN(C)C2CCCc3cccnc32)nc2ccccc21"
},
"smiles": "COC(=O)Cn1c(CN(C)C2CCCc3cccnc32)nc2ccccc21",
"reactionStepId": "sa_c03eb36734969b31f32fd1fb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080096861A1;0508;565564\",\"rsmi\":\"Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[nH:6]1[c:7]([CH2:8][N:9]([CH3:10])[CH:11]2[CH2:12][CH2:13][CH2:14][c:15]3[c:16]2[n:17][cH:18][cH:19][cH:20]3)[n:21][c:22]2[c:23]1[cH:24][cH:25][cH:26][cH:27]2>CCOC(C)=O.CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][n:6]1[c:7]([CH2:8][N:9]([CH3:10])[CH:11]2[CH2:12][CH2:13][CH2:14][c:15]3[c:16]2[n:17][cH:18][cH:19][cH:20]3)[n:21][c:22]2[c:23]1[cH:24][cH:25][cH:26][cH:27]2\"},\"mapped_reaction_smiles\":\"Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[nH:6]1[c:7]([CH2:8][N:9]([CH3:10])[CH:11]2[CH2:12][CH2:13][CH2:14][c:15]3[c:16]2[n:17][cH:18][cH:19][cH:20]3)[n:21][c:22]2[c:23]1[cH:24][cH:25][cH:26][cH:27]2>CCOC(C)=O.CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][n:6]1[c:7]([CH2:8][N:9]([CH3:10])[CH:11]2[CH2:12][CH2:13][CH2:14][c:15]3[c:16]2[n:17][cH:18][cH:19][cH:20]3)[n:21][c:22]2[c:23]1[cH:24][cH:25][cH:26][cH:27]2\"}",
"reactionStep": {
"id": "sa_c03eb36734969b31f32fd1fb",
"reactionHash": "e79022ce84c2613f6e9d6beecb14af90a7477c11b7717836e1364ea84a42efd5"
},
"children": [
{
"id": "6342",
"routeId": "sa_b92556d80f2dbc3a428b2c75",
"moleculeId": "sa_091a3533e2daf28ddc2b5e73",
"parentId": "6341",
"isLeaf": false,
"molecule": {
"id": "sa_091a3533e2daf28ddc2b5e73",
"inchikey": "FSHOCXHHNGCGBX-UHFFFAOYSA-N",
"smiles": "CN(Cc1nc2ccccc2[nH]1)C1CCCc2cccnc21"
},
"smiles": "CN(Cc1nc2ccccc2[nH]1)C1CCCc2cccnc21",
"reactionStepId": "sa_e43d525b4913367caca58175",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080096861A1;0402;565488\",\"rsmi\":\"O=[CH2:1].[NH:2]([CH2:3][c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[nH:12]1)[CH:13]1[CH2:14][CH2:15][CH2:16][c:17]2[c:18]1[n:19][cH:20][cH:21][cH:22]2>CC(=O)O.CC(=O)OB(OC(C)=O)OC(C)=O.ClCCCl.ClCCl.O=C(O)O.[Na+].[Na+].[Na+]>[CH3:1][N:2]([CH2:3][c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[nH:12]1)[CH:13]1[CH2:14][CH2:15][CH2:16][c:17]2[c:18]1[n:19][cH:20][cH:21][cH:22]2\"},\"mapped_reaction_smiles\":\"O=[CH2:1].[NH:2]([CH2:3][c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[nH:12]1)[CH:13]1[CH2:14][CH2:15][CH2:16][c:17]2[c:18]1[n:19][cH:20][cH:21][cH:22]2>CC(=O)O.CC(=O)OB(OC(C)=O)OC(C)=O.ClCCCl.ClCCl.O=C(O)O.[Na+].[Na+].[Na+]>[CH3:1][N:2]([CH2:3][c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[nH:12]1)[CH:13]1[CH2:14][CH2:15][CH2:16][c:17]2[c:18]1[n:19][cH:20][cH:21][cH:22]2\"}",
"reactionStep": {
"id": "sa_e43d525b4913367caca58175",
"reactionHash": "c557901b855fbbde1f7a429ae2d7953c67f9b9ba8418aab0949e0118d5bfecd6"
},
"children": [
{
"id": "6343",
"routeId": "sa_b92556d80f2dbc3a428b2c75",
"moleculeId": "sa_fa48b0311f9ecb906b2132fe",
"parentId": "6342",
"isLeaf": true,
"molecule": {
"id": "sa_fa48b0311f9ecb906b2132fe",
"inchikey": "WSFSSNUMVMOOMR-UHFFFAOYSA-N",
"smiles": "C=O"
},
"smiles": "C=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6344",
"routeId": "sa_b92556d80f2dbc3a428b2c75",
"moleculeId": "sa_eb974cdaafaf2f83176e32b7",
"parentId": "6342",
"isLeaf": false,
"molecule": {
"id": "sa_eb974cdaafaf2f83176e32b7",
"inchikey": "YIWUDZZUTVWTFZ-UHFFFAOYSA-N",
"smiles": "c1cnc2c(c1)CCCC2NCc1nc2ccccc2[nH]1"
},
"smiles": "c1cnc2c(c1)CCCC2NCc1nc2ccccc2[nH]1",
"reactionStepId": "sa_356850c67210b0285e6104bf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080096861A1;0400;565487\",\"rsmi\":\"O=[C:7]1[c:4]2[c:3]([cH:2][cH:1][cH:6][n:5]2)[CH2:21][CH2:20][CH2:19]1.[NH2:8][CH2:9][c:10]1[n:11][c:12]2[c:13]([cH:14][cH:15][cH:16][cH:17]2)[nH:18]1>CO.Cl.Cl.B.[Na+]>[cH:1]1[cH:2][c:3]2[c:4]([n:5][cH:6]1)[CH:7]([NH:8][CH2:9][c:10]1[n:11][c:12]3[c:13]([cH:14][cH:15][cH:16][cH:17]3)[nH:18]1)[CH2:19][CH2:20][CH2:21]2\"},\"mapped_reaction_smiles\":\"O=[C:7]1[c:4]2[c:3]([cH:2][cH:1][cH:6][n:5]2)[CH2:21][CH2:20][CH2:19]1.[NH2:8][CH2:9][c:10]1[n:11][c:12]2[c:13]([cH:14][cH:15][cH:16][cH:17]2)[nH:18]1>CO.Cl.Cl.B.[Na+]>[cH:1]1[cH:2][c:3]2[c:4]([n:5][cH:6]1)[CH:7]([NH:8][CH2:9][c:10]1[n:11][c:12]3[c:13]([cH:14][cH:15][cH:16][cH:17]3)[nH:18]1)[CH2:19][CH2:20][CH2:21]2\"}",
"reactionStep": {
"id": "sa_356850c67210b0285e6104bf",
"reactionHash": "bb17d126d26d72e337eeec8378320a926940fe9e270062f8391289b44e94698f"
},
"children": [
{
"id": "6345",
"routeId": "sa_b92556d80f2dbc3a428b2c75",
"moleculeId": "sa_73a6a0cfff992e5b0e17db9c",
"parentId": "6344",
"isLeaf": true,
"molecule": {
"id": "sa_73a6a0cfff992e5b0e17db9c",
"inchikey": "JIAKIQWNYAZUJD-UHFFFAOYSA-N",
"smiles": "O=C1CCCc2cccnc21"
},
"smiles": "O=C1CCCc2cccnc21",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6346",
"routeId": "sa_b92556d80f2dbc3a428b2c75",
"moleculeId": "sa_c0517e39c0307015d5d123d3",
"parentId": "6344",
"isLeaf": true,
"molecule": {
"id": "sa_c0517e39c0307015d5d123d3",
"inchikey": "UCOSRTUSVXHIMK-UHFFFAOYSA-N",
"smiles": "NCc1nc2ccccc2[nH]1"
},
"smiles": "NCc1nc2ccccc2[nH]1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "6347",
"routeId": "sa_b92556d80f2dbc3a428b2c75",
"moleculeId": "sa_d6971278542e932ae568b29f",
"parentId": "6341",
"isLeaf": true,
"molecule": {
"id": "sa_d6971278542e932ae568b29f",
"inchikey": "YDCHPLOFQATIDS-UHFFFAOYSA-N",
"smiles": "COC(=O)CBr"
},
"smiles": "COC(=O)CBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "6348",
"routeId": "sa_b92556d80f2dbc3a428b2c75",
"moleculeId": "sa_e688c47a0eb4ca67c35ad0bd",
"parentId": "6339",
"isLeaf": true,
"molecule": {
"id": "sa_e688c47a0eb4ca67c35ad0bd",
"inchikey": "WOXFMYVTSLAQMO-UHFFFAOYSA-N",
"smiles": "NCc1ccccn1"
},
"smiles": "NCc1ccccn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}