Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C=CC(=O)Nc1cc(Nc2nccc(-c3cnn4c3CCCC4)n2)c(OC)cc1N1CC2(CCCN2C)C1
InChiKey
GSMDMDKOGLGSPR-UHFFFAOYSA-N
Route Signature
89115914321b2da33063ac51accdbd96526da5dbe6ee7f0330e5668d0bbf2c00
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_4dd45a89f2327b1a0bda6cfc",
"signature": "89115914321b2da33063ac51accdbd96526da5dbe6ee7f0330e5668d0bbf2c00",
"contentHash": "0ba9fdfeba5241225c29eff6015d87d92593a402727693211014241927cafb2c",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_6764f96885d7e44420390eb8",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02100",
"moleculeId": "sa_ce89194dda7b45515ae2ac74",
"smiles": "C=CC(=O)Nc1cc(Nc2nccc(-c3cnn4c3CCCC4)n2)c(OC)cc1N1CC2(CCCN2C)C1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_ce89194dda7b45515ae2ac74",
"inchikey": "GSMDMDKOGLGSPR-UHFFFAOYSA-N",
"smiles": "C=CC(=O)Nc1cc(Nc2nccc(-c3cnn4c3CCCC4)n2)c(OC)cc1N1CC2(CCCN2C)C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10596",
"routeId": "sa_4dd45a89f2327b1a0bda6cfc",
"moleculeId": "sa_ce89194dda7b45515ae2ac74",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_ce89194dda7b45515ae2ac74",
"inchikey": "GSMDMDKOGLGSPR-UHFFFAOYSA-N",
"smiles": "C=CC(=O)Nc1cc(Nc2nccc(-c3cnn4c3CCCC4)n2)c(OC)cc1N1CC2(CCCN2C)C1"
},
"smiles": "C=CC(=O)Nc1cc(Nc2nccc(-c3cnn4c3CCCC4)n2)c(OC)cc1N1CC2(CCCN2C)C1",
"reactionStepId": "sa_cc3f6ed305e2f76fe41a886e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150119379A1;0520;1682359\",\"rsmi\":\"Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH2:5][c:6]1[c:7]([N:8]2[CH2:9][C:10]3([CH2:11][CH2:12][CH2:13][N:14]3[CH3:15])[CH2:16]2)[cH:17][c:18]([O:19][CH3:20])[c:21]([NH:22][c:23]2[n:24][cH:25][cH:26][c:27](-[c:28]3[c:29]4[n:34]([n:35][cH:36]3)[CH2:33][CH2:32][CH2:31][CH2:30]4)[n:37]2)[cH:38]1>CCN(C(C)C)C(C)C.ClCCl>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][c:6]1[c:7]([N:8]2[CH2:9][C:10]3([CH2:11][CH2:12][CH2:13][N:14]3[CH3:15])[CH2:16]2)[cH:17][c:18]([O:19][CH3:20])[c:21]([NH:22][c:23]2[n:24][cH:25][cH:26][c:27](-[c:28]3[c:29]4[n:34]([n:35][cH:36]3)[CH2:33][CH2:32][CH2:31][CH2:30]4)[n:37]2)[cH:38]1\"},\"mapped_reaction_smiles\":\"Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH2:5][c:6]1[c:7]([N:8]2[CH2:9][C:10]3([CH2:11][CH2:12][CH2:13][N:14]3[CH3:15])[CH2:16]2)[cH:17][c:18]([O:19][CH3:20])[c:21]([NH:22][c:23]2[n:24][cH:25][cH:26][c:27](-[c:28]3[c:29]4[n:34]([n:35][cH:36]3)[CH2:33][CH2:32][CH2:31][CH2:30]4)[n:37]2)[cH:38]1>CCN(C(C)C)C(C)C.ClCCl>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][c:6]1[c:7]([N:8]2[CH2:9][C:10]3([CH2:11][CH2:12][CH2:13][N:14]3[CH3:15])[CH2:16]2)[cH:17][c:18]([O:19][CH3:20])[c:21]([NH:22][c:23]2[n:24][cH:25][cH:26][c:27](-[c:28]3[c:29]4[n:34]([n:35][cH:36]3)[CH2:33][CH2:32][CH2:31][CH2:30]4)[n:37]2)[cH:38]1\"}",
"reactionStep": {
"id": "sa_cc3f6ed305e2f76fe41a886e",
"reactionHash": "1b2b55a45d6dedddee7e3549a01c4e999effd3ceaa51a62e0b8e5d4d422067f1"
},
"children": [
{
"id": "10597",
"routeId": "sa_4dd45a89f2327b1a0bda6cfc",
"moleculeId": "sa_0b4e45c0d9e46a5808f6bc17",
"parentId": "10596",
"isLeaf": true,
"molecule": {
"id": "sa_0b4e45c0d9e46a5808f6bc17",
"inchikey": "HFBMWMNUJJDEQZ-UHFFFAOYSA-N",
"smiles": "C=CC(=O)Cl"
},
"smiles": "C=CC(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10598",
"routeId": "sa_4dd45a89f2327b1a0bda6cfc",
"moleculeId": "sa_2cff82d6e8804731aed1374a",
"parentId": "10596",
"isLeaf": false,
"molecule": {
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"inchikey": "HWRXHFBUXUAFMF-UHFFFAOYSA-N",
"smiles": "COc1cc(N2CC3(CCCN3C)C2)c(N)cc1Nc1nccc(-c2cnn3c2CCCC3)n1"
},
"smiles": "COc1cc(N2CC3(CCCN3C)C2)c(N)cc1Nc1nccc(-c2cnn3c2CCCC3)n1",
"reactionStepId": "sa_4a44fae7832ffa11ffa8fd64",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150119379A1;0690;1682499\",\"rsmi\":\"O=[N+:23]([O-])[c:22]1[cH:21][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[c:12]4[n:17]([n:18][cH:19]3)[CH2:16][CH2:15][CH2:14][CH2:13]4)[n:20]2)[c:3]([O:2][CH3:1])[cH:34][c:24]1[N:25]1[CH2:26][C:27]2([CH2:28][CH2:29][CH2:30][N:31]2[CH3:32])[CH2:33]1>CCO.O.Cl.[Fe].N>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[c:12]4[n:17]([n:18][cH:19]3)[CH2:16][CH2:15][CH2:14][CH2:13]4)[n:20]2)[cH:21][c:22]([NH2:23])[c:24]([N:25]2[CH2:26][C:27]3([CH2:28][CH2:29][CH2:30][N:31]3[CH3:32])[CH2:33]2)[cH:34]1\"},\"mapped_reaction_smiles\":\"O=[N+:23]([O-])[c:22]1[cH:21][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[c:12]4[n:17]([n:18][cH:19]3)[CH2:16][CH2:15][CH2:14][CH2:13]4)[n:20]2)[c:3]([O:2][CH3:1])[cH:34][c:24]1[N:25]1[CH2:26][C:27]2([CH2:28][CH2:29][CH2:30][N:31]2[CH3:32])[CH2:33]1>CCO.O.Cl.[Fe].N>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[c:12]4[n:17]([n:18][cH:19]3)[CH2:16][CH2:15][CH2:14][CH2:13]4)[n:20]2)[cH:21][c:22]([NH2:23])[c:24]([N:25]2[CH2:26][C:27]3([CH2:28][CH2:29][CH2:30][N:31]3[CH3:32])[CH2:33]2)[cH:34]1\"}",
"reactionStep": {
"id": "sa_4a44fae7832ffa11ffa8fd64",
"reactionHash": "80dec18164f7875c9b520806c6d34f78ecbad1aa7f118b7e9accd1ff7866aa7c"
},
"children": [
{
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"routeId": "sa_4dd45a89f2327b1a0bda6cfc",
"moleculeId": "sa_88350efb36a55e2f23528530",
"parentId": "10598",
"isLeaf": false,
"molecule": {
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"inchikey": "AJCVHRIVQAAELE-UHFFFAOYSA-N",
"smiles": "COc1cc(N2CC3(CCCN3C)C2)c([N+](=O)[O-])cc1Nc1nccc(-c2cnn3c2CCCC3)n1"
},
"smiles": "COc1cc(N2CC3(CCCN3C)C2)c([N+](=O)[O-])cc1Nc1nccc(-c2cnn3c2CCCC3)n1",
"reactionStepId": "sa_657fe537cf49e8b317bba8d6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150119379A1;0691;1682500\",\"rsmi\":\"F[c:26]1[c:22]([N+:23](=[O:24])[O-:25])[cH:21][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[c:12]4[n:17]([n:18][cH:19]3)[CH2:16][CH2:15][CH2:14][CH2:13]4)[n:20]2)[c:3]([O:2][CH3:1])[cH:36]1.[NH:27]1[CH2:28][C:29]2([CH2:30][CH2:31][CH2:32][N:33]2[CH3:34])[CH2:35]1>CC(=O)N(C)C.CCN(C(C)C)C(C)C.Cl.Cl>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[c:12]4[n:17]([n:18][cH:19]3)[CH2:16][CH2:15][CH2:14][CH2:13]4)[n:20]2)[cH:21][c:22]([N+:23](=[O:24])[O-:25])[c:26]([N:27]2[CH2:28][C:29]3([CH2:30][CH2:31][CH2:32][N:33]3[CH3:34])[CH2:35]2)[cH:36]1\"},\"mapped_reaction_smiles\":\"F[c:26]1[c:22]([N+:23](=[O:24])[O-:25])[cH:21][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[c:12]4[n:17]([n:18][cH:19]3)[CH2:16][CH2:15][CH2:14][CH2:13]4)[n:20]2)[c:3]([O:2][CH3:1])[cH:36]1.[NH:27]1[CH2:28][C:29]2([CH2:30][CH2:31][CH2:32][N:33]2[CH3:34])[CH2:35]1>CC(=O)N(C)C.CCN(C(C)C)C(C)C.Cl.Cl>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[c:12]4[n:17]([n:18][cH:19]3)[CH2:16][CH2:15][CH2:14][CH2:13]4)[n:20]2)[cH:21][c:22]([N+:23](=[O:24])[O-:25])[c:26]([N:27]2[CH2:28][C:29]3([CH2:30][CH2:31][CH2:32][N:33]3[CH3:34])[CH2:35]2)[cH:36]1\"}",
"reactionStep": {
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"reactionHash": "8ad115527ab38d03caf0fbdc45b64e9f485bae5b5f9f81c07cba9a88c61cbb0d"
},
"children": [
{
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"routeId": "sa_4dd45a89f2327b1a0bda6cfc",
"moleculeId": "sa_f1e25e92991ef25e94dcbf9d",
"parentId": "10599",
"isLeaf": true,
"molecule": {
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"inchikey": "GMRSNDRXDYVEAG-UHFFFAOYSA-N",
"smiles": "CN1CCCC12CNC2"
},
"smiles": "CN1CCCC12CNC2",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "10601",
"routeId": "sa_4dd45a89f2327b1a0bda6cfc",
"moleculeId": "sa_d8a0762e3acb07d8c427ba97",
"parentId": "10599",
"isLeaf": false,
"molecule": {
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"inchikey": "YNVZVWCQSLXRJU-UHFFFAOYSA-N",
"smiles": "COc1cc(F)c([N+](=O)[O-])cc1Nc1nccc(-c2cnn3c2CCCC3)n1"
},
"smiles": "COc1cc(F)c([N+](=O)[O-])cc1Nc1nccc(-c2cnn3c2CCCC3)n1",
"reactionStepId": "sa_911305940a37c2c875f62ab0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150119379A1;0673;1682485\",\"rsmi\":\"Cl[c:6]1[n:7][cH:8][cH:9][c:10](-[c:11]2[c:12]3[n:17]([n:18][cH:19]2)[CH2:16][CH2:15][CH2:14][CH2:13]3)[n:20]1.[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:21][c:22]([N+:23](=[O:24])[O-:25])[c:26]([F:27])[cH:28]1>CCCC(C)O.Cc1ccc(S(=O)(=O)O)cc1.O>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[c:12]4[n:17]([n:18][cH:19]3)[CH2:16][CH2:15][CH2:14][CH2:13]4)[n:20]2)[cH:21][c:22]([N+:23](=[O:24])[O-:25])[c:26]([F:27])[cH:28]1\"},\"mapped_reaction_smiles\":\"Cl[c:6]1[n:7][cH:8][cH:9][c:10](-[c:11]2[c:12]3[n:17]([n:18][cH:19]2)[CH2:16][CH2:15][CH2:14][CH2:13]3)[n:20]1.[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:21][c:22]([N+:23](=[O:24])[O-:25])[c:26]([F:27])[cH:28]1>CCCC(C)O.Cc1ccc(S(=O)(=O)O)cc1.O>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10](-[c:11]3[c:12]4[n:17]([n:18][cH:19]3)[CH2:16][CH2:15][CH2:14][CH2:13]4)[n:20]2)[cH:21][c:22]([N+:23](=[O:24])[O-:25])[c:26]([F:27])[cH:28]1\"}",
"reactionStep": {
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"molecule": {
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"inchikey": "FYSIGSQCZXQTIH-UHFFFAOYSA-N",
"smiles": "COc1cc(F)c([N+](=O)[O-])cc1N"
},
"smiles": "COc1cc(F)c([N+](=O)[O-])cc1N",
"reactionStepId": "sa_2accc798f21241202b09b4e4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150119379A1;0558;1682394\",\"rsmi\":\"[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:6][cH:7][c:11]([F:12])[cH:13]1.O[N+:8](=[O:9])[O-:10]>O=S(=O)(O)O.[K+].N.O>[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([F:12])[cH:13]1\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:6][cH:7][c:11]([F:12])[cH:13]1.O[N+:8](=[O:9])[O-:10]>O=S(=O)(O)O.[K+].N.O>[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([F:12])[cH:13]1\"}",
"reactionStep": {
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"children": [
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"molecule": {
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"smiles": "COc1cc(F)ccc1N"
},
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{
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"molecule": {
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"smiles": "O=[N+]([O-])O"
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{
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},
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"reactionStepId": "sa_a8d03ccc60d685accf19ad2a",
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"reactionStep": {
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"children": [
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},
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},
{
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},
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]
}
]
}
]
}
]
}
]
}
}