Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCc1ccc(C(=O)N2CCC(c3ccc(-c4cnn(C)c4)cc3)CC2)cc1N
InChiKey
HMXBXQYZVUIJMK-UHFFFAOYSA-N
Route Signature
0f67c90455c02fd39ad580282701c6f41f4928f337e789c4dd78738ff9d7fb69
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_9f41a76033a0c3ea23785bf6",
"signature": "0f67c90455c02fd39ad580282701c6f41f4928f337e789c4dd78738ff9d7fb69",
"contentHash": "19fd4bf1ddfec8ab9153804cbe31eb2de42b2cee8c217cab9d26de9aa14a3ab8",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_7df0ce1a5ef7a61a9a787523",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-05468",
"moleculeId": "sa_67d8b647220cdabe1185aebd",
"smiles": "CCc1ccc(C(=O)N2CCC(c3ccc(-c4cnn(C)c4)cc3)CC2)cc1N",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_67d8b647220cdabe1185aebd",
"inchikey": "HMXBXQYZVUIJMK-UHFFFAOYSA-N",
"smiles": "CCc1ccc(C(=O)N2CCC(c3ccc(-c4cnn(C)c4)cc3)CC2)cc1N"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "2827",
"routeId": "sa_9f41a76033a0c3ea23785bf6",
"moleculeId": "sa_67d8b647220cdabe1185aebd",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_67d8b647220cdabe1185aebd",
"inchikey": "HMXBXQYZVUIJMK-UHFFFAOYSA-N",
"smiles": "CCc1ccc(C(=O)N2CCC(c3ccc(-c4cnn(C)c4)cc3)CC2)cc1N"
},
"smiles": "CCc1ccc(C(=O)N2CCC(c3ccc(-c4cnn(C)c4)cc3)CC2)cc1N",
"reactionStepId": "sa_02ca9808717022b5b1532027",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160009688A1;0459;1818188\",\"rsmi\":\"O[C:8]([c:7]1[cH:6][c:4]([NH2:5])[c:3]([CH2:2][CH3:1])[cH:29][cH:28]1)=[O:9].[NH:10]1[CH2:11][CH2:12][CH:13]([c:14]2[cH:15][cH:16][c:17](-[c:18]3[cH:19][n:20]([CH3:21])[n:22][cH:23]3)[cH:24][cH:25]2)[CH2:26][CH2:27]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.ClCCl.F[PH](F)(F)(F)(F)F.O=C(O)O.[Na+].[Na+]>[CH3:1][CH2:2][c:3]1[c:4]([NH2:5])[cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][CH2:12][CH:13]([c:14]3[cH:15][cH:16][c:17](-[c:18]4[cH:19][n:20]([CH3:21])[n:22][cH:23]4)[cH:24][cH:25]3)[CH2:26][CH2:27]2)[cH:28][cH:29]1\"},\"mapped_reaction_smiles\":\"O[C:8]([c:7]1[cH:6][c:4]([NH2:5])[c:3]([CH2:2][CH3:1])[cH:29][cH:28]1)=[O:9].[NH:10]1[CH2:11][CH2:12][CH:13]([c:14]2[cH:15][cH:16][c:17](-[c:18]3[cH:19][n:20]([CH3:21])[n:22][cH:23]3)[cH:24][cH:25]2)[CH2:26][CH2:27]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.ClCCl.F[PH](F)(F)(F)(F)F.O=C(O)O.[Na+].[Na+]>[CH3:1][CH2:2][c:3]1[c:4]([NH2:5])[cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][CH2:12][CH:13]([c:14]3[cH:15][cH:16][c:17](-[c:18]4[cH:19][n:20]([CH3:21])[n:22][cH:23]4)[cH:24][cH:25]3)[CH2:26][CH2:27]2)[cH:28][cH:29]1\"}",
"reactionStep": {
"id": "sa_02ca9808717022b5b1532027",
"reactionHash": "877cec20fc296aace7f116dfa1dab8ae760698752a2dbf544fd4396bae2b7081"
},
"children": [
{
"id": "2828",
"routeId": "sa_9f41a76033a0c3ea23785bf6",
"moleculeId": "sa_b10d76a6dbc2fc3002d71b5f",
"parentId": "2827",
"isLeaf": false,
"molecule": {
"id": "sa_b10d76a6dbc2fc3002d71b5f",
"inchikey": "LLZSVDFDTYGEEG-UHFFFAOYSA-N",
"smiles": "CCc1ccc(C(=O)O)cc1N"
},
"smiles": "CCc1ccc(C(=O)O)cc1N",
"reactionStepId": "sa_cb9f960657362193270e2946",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160009688A1;0458;1818187\",\"rsmi\":\"O=[N+:5]([O-])[c:4]1[c:3]([CH2:2][CH3:1])[cH:12][cH:11][c:7]([C:8](=[O:9])[OH:10])[cH:6]1>CO.[Pd]>[CH3:1][CH2:2][c:3]1[c:4]([NH2:5])[cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12]1\"},\"mapped_reaction_smiles\":\"O=[N+:5]([O-])[c:4]1[c:3]([CH2:2][CH3:1])[cH:12][cH:11][c:7]([C:8](=[O:9])[OH:10])[cH:6]1>CO.[Pd]>[CH3:1][CH2:2][c:3]1[c:4]([NH2:5])[cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12]1\"}",
"reactionStep": {
"id": "sa_cb9f960657362193270e2946",
"reactionHash": "601758893c5b3565cb6405d033f226b39ff12c0b158934a85d6534d9ee1cfd79"
},
"children": [
{
"id": "2829",
"routeId": "sa_9f41a76033a0c3ea23785bf6",
"moleculeId": "sa_b6006442b43d72acc80dc922",
"parentId": "2828",
"isLeaf": false,
"molecule": {
"id": "sa_b6006442b43d72acc80dc922",
"inchikey": "DUTYVLOGZGRKMA-UHFFFAOYSA-N",
"smiles": "CCc1ccc(C(=O)O)cc1[N+](=O)[O-]"
},
"smiles": "CCc1ccc(C(=O)O)cc1[N+](=O)[O-]",
"reactionStepId": "sa_3131ed0d412dfccb0f0f4e0a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160009688A1;0457;1818186\",\"rsmi\":\"O[N+:5](=[O:6])[O-:7].[CH3:1][CH2:2][c:3]1[cH:4][cH:8][c:9]([C:10](=[O:11])[OH:12])[cH:13][cH:14]1>O.O=S(=O)(O)O>[CH3:1][CH2:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([C:10](=[O:11])[OH:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"O[N+:5](=[O:6])[O-:7].[CH3:1][CH2:2][c:3]1[cH:4][cH:8][c:9]([C:10](=[O:11])[OH:12])[cH:13][cH:14]1>O.O=S(=O)(O)O>[CH3:1][CH2:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([C:10](=[O:11])[OH:12])[cH:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_3131ed0d412dfccb0f0f4e0a",
"reactionHash": "1aae667241283ddcac1479739d6cd6d390b916e64a84308730e674c17c90f15c"
},
"children": [
{
"id": "2830",
"routeId": "sa_9f41a76033a0c3ea23785bf6",
"moleculeId": "sa_edac0a7fd043198784a28dd9",
"parentId": "2829",
"isLeaf": true,
"molecule": {
"id": "sa_edac0a7fd043198784a28dd9",
"inchikey": "GRYLNZFGIOXLOG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])O"
},
"smiles": "O=[N+]([O-])O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2831",
"routeId": "sa_9f41a76033a0c3ea23785bf6",
"moleculeId": "sa_f11dcce34d9a7e3a46e48976",
"parentId": "2829",
"isLeaf": true,
"molecule": {
"id": "sa_f11dcce34d9a7e3a46e48976",
"inchikey": "ZQVKTHRQIXSMGY-UHFFFAOYSA-N",
"smiles": "CCc1ccc(C(=O)O)cc1"
},
"smiles": "CCc1ccc(C(=O)O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "2832",
"routeId": "sa_9f41a76033a0c3ea23785bf6",
"moleculeId": "sa_ade282d4001701df020c6226",
"parentId": "2827",
"isLeaf": false,
"molecule": {
"id": "sa_ade282d4001701df020c6226",
"inchikey": "OGJKUKJAPYSUND-UHFFFAOYSA-N",
"smiles": "Cn1cc(-c2ccc(C3CCNCC3)cc2)cn1"
},
"smiles": "Cn1cc(-c2ccc(C3CCNCC3)cc2)cn1",
"reactionStepId": "sa_7ff4518eee07786af02d3910",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160009688A1;0446;1818179\",\"rsmi\":\"[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]3=[CH:10][CH2:11][NH:12][CH2:13][CH2:14]3)[cH:15][cH:16]2)[cH:17][n:18]1>CO.[Pd]>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([CH:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[cH:15][cH:16]2)[cH:17][n:18]1\"},\"mapped_reaction_smiles\":\"[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]3=[CH:10][CH2:11][NH:12][CH2:13][CH2:14]3)[cH:15][cH:16]2)[cH:17][n:18]1>CO.[Pd]>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([CH:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[cH:15][cH:16]2)[cH:17][n:18]1\"}",
"reactionStep": {
"id": "sa_7ff4518eee07786af02d3910",
"reactionHash": "f255329ca8981f012bd77f105afa80d7565726234bdb51aa2c3412d28d3c917e"
},
"children": [
{
"id": "2833",
"routeId": "sa_9f41a76033a0c3ea23785bf6",
"moleculeId": "sa_bc4ad5a715933ef631dff6e6",
"parentId": "2832",
"isLeaf": false,
"molecule": {
"id": "sa_bc4ad5a715933ef631dff6e6",
"inchikey": "TYRFQTLHOGMVPR-UHFFFAOYSA-N",
"smiles": "Cn1cc(-c2ccc(C3=CCNCC3)cc2)cn1"
},
"smiles": "Cn1cc(-c2ccc(C3=CCNCC3)cc2)cn1",
"reactionStepId": "sa_28b6b1855b287abb24b73da0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160009688A1;0445;1818178\",\"rsmi\":\"Br[c:5]1[cH:6][cH:7][c:8]([C:9]2=[CH:10][CH2:11][NH:12][CH2:13][CH2:14]2)[cH:15][cH:16]1.CC1(C)OB([c:4]2[cH:3][n:2]([CH3:1])[n:18][cH:17]2)OC1(C)C>C1COCCO1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(O)C(F)(F)F.O=C(O)O.[Na+].[Na+]>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]3=[CH:10][CH2:11][NH:12][CH2:13][CH2:14]3)[cH:15][cH:16]2)[cH:17][n:18]1\"},\"mapped_reaction_smiles\":\"Br[c:5]1[cH:6][cH:7][c:8]([C:9]2=[CH:10][CH2:11][NH:12][CH2:13][CH2:14]2)[cH:15][cH:16]1.CC1(C)OB([c:4]2[cH:3][n:2]([CH3:1])[n:18][cH:17]2)OC1(C)C>C1COCCO1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(O)C(F)(F)F.O=C(O)O.[Na+].[Na+]>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]3=[CH:10][CH2:11][NH:12][CH2:13][CH2:14]3)[cH:15][cH:16]2)[cH:17][n:18]1\"}",
"reactionStep": {
"id": "sa_28b6b1855b287abb24b73da0",
"reactionHash": "dfb1a8bf696e974b87ffbee6c2ff9016d49486b61441f0548ecfa0b786b0737c"
},
"children": [
{
"id": "2834",
"routeId": "sa_9f41a76033a0c3ea23785bf6",
"moleculeId": "sa_8a74adbc0468ed648bfcce61",
"parentId": "2833",
"isLeaf": true,
"molecule": {
"id": "sa_8a74adbc0468ed648bfcce61",
"inchikey": "FDRGGAPHXGEHPI-UHFFFAOYSA-N",
"smiles": "Brc1ccc(C2=CCNCC2)cc1"
},
"smiles": "Brc1ccc(C2=CCNCC2)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2835",
"routeId": "sa_9f41a76033a0c3ea23785bf6",
"moleculeId": "sa_8ccec6fc9194e5fbc0d06993",
"parentId": "2833",
"isLeaf": true,
"molecule": {
"id": "sa_8ccec6fc9194e5fbc0d06993",
"inchikey": "UCNGGGYMLHAMJG-UHFFFAOYSA-N",
"smiles": "Cn1cc(B2OC(C)(C)C(C)(C)O2)cn1"
},
"smiles": "Cn1cc(B2OC(C)(C)C(C)(C)O2)cn1",
"reactionStepId": null,
"template": null,
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}
]
}
]
}
]
}
}