Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(Nc1ccc2[nH]nc(-c3nc4ccccc4[nH]3)c2c1)C1CCN(c2ccncc2)CC1
InChiKey
NJXQUYNZYIQURR-UHFFFAOYSA-N
Route Signature
a4f50fc2b158e5ae5a8424b8399c83f60bca54f55bec2af0e5feaf19c1068fb8
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_bd9b318cb85c04f8b825ae87",
"signature": "a4f50fc2b158e5ae5a8424b8399c83f60bca54f55bec2af0e5feaf19c1068fb8",
"contentHash": "6667e40c30e19520d91e07a6cb148646a44f6b0d538ddf858832731538ee0066",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_e1e4051474eda815fb4c8f11",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-03647",
"moleculeId": "sa_f8dc8e0276540a13f2edeee7",
"smiles": "O=C(Nc1ccc2[nH]nc(-c3nc4ccccc4[nH]3)c2c1)C1CCN(c2ccncc2)CC1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_f8dc8e0276540a13f2edeee7",
"inchikey": "NJXQUYNZYIQURR-UHFFFAOYSA-N",
"smiles": "O=C(Nc1ccc2[nH]nc(-c3nc4ccccc4[nH]3)c2c1)C1CCN(c2ccncc2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "6990",
"routeId": "sa_bd9b318cb85c04f8b825ae87",
"moleculeId": "sa_f8dc8e0276540a13f2edeee7",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f8dc8e0276540a13f2edeee7",
"inchikey": "NJXQUYNZYIQURR-UHFFFAOYSA-N",
"smiles": "O=C(Nc1ccc2[nH]nc(-c3nc4ccccc4[nH]3)c2c1)C1CCN(c2ccncc2)CC1"
},
"smiles": "O=C(Nc1ccc2[nH]nc(-c3nc4ccccc4[nH]3)c2c1)C1CCN(c2ccncc2)CC1",
"reactionStepId": "sa_afaf959705f43d3af0439faf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08569511B2;0607;1383226\",\"rsmi\":\"C1CCC([n:8]2[c:7]3[cH:6][cH:5][c:4]([NH:3][C:2](=[O:1])[CH:22]4[CH2:23][CH2:24][N:25]([c:26]5[cH:27][cH:28][n:29][cH:30][cH:31]5)[CH2:32][CH2:33]4)[cH:21][c:20]3[c:10](-[c:11]3[n:12][c:13]4[c:14]([cH:15][cH:16][cH:17][cH:18]4)[nH:19]3)[n:9]2)OC1>ClCCl.O=C(O)C(F)(F)F>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]2[nH:8][n:9][c:10](-[c:11]3[n:12][c:13]4[c:14]([cH:15][cH:16][cH:17][cH:18]4)[nH:19]3)[c:20]2[cH:21]1)[CH:22]1[CH2:23][CH2:24][N:25]([c:26]2[cH:27][cH:28][n:29][cH:30][cH:31]2)[CH2:32][CH2:33]1\"},\"mapped_reaction_smiles\":\"C1CCC([n:8]2[c:7]3[cH:6][cH:5][c:4]([NH:3][C:2](=[O:1])[CH:22]4[CH2:23][CH2:24][N:25]([c:26]5[cH:27][cH:28][n:29][cH:30][cH:31]5)[CH2:32][CH2:33]4)[cH:21][c:20]3[c:10](-[c:11]3[n:12][c:13]4[c:14]([cH:15][cH:16][cH:17][cH:18]4)[nH:19]3)[n:9]2)OC1>ClCCl.O=C(O)C(F)(F)F>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]2[nH:8][n:9][c:10](-[c:11]3[n:12][c:13]4[c:14]([cH:15][cH:16][cH:17][cH:18]4)[nH:19]3)[c:20]2[cH:21]1)[CH:22]1[CH2:23][CH2:24][N:25]([c:26]2[cH:27][cH:28][n:29][cH:30][cH:31]2)[CH2:32][CH2:33]1\"}",
"reactionStep": {
"id": "sa_afaf959705f43d3af0439faf",
"reactionHash": "b892c72981948deadb86f3cde6403acbeb734aeb715853034fad40528af66298"
},
"children": [
{
"id": "6991",
"routeId": "sa_bd9b318cb85c04f8b825ae87",
"moleculeId": "sa_0a4308b1a9dbceb7b34d3887",
"parentId": "6990",
"isLeaf": false,
"molecule": {
"id": "sa_0a4308b1a9dbceb7b34d3887",
"inchikey": "OWBHIYRNLAHXKZ-UHFFFAOYSA-N",
"smiles": "O=C(Nc1ccc2c(c1)c(-c1nc3ccccc3[nH]1)nn2C1CCCCO1)C1CCN(c2ccncc2)CC1"
},
"smiles": "O=C(Nc1ccc2c(c1)c(-c1nc3ccccc3[nH]1)nn2C1CCCCO1)C1CCN(c2ccncc2)CC1",
"reactionStepId": "sa_7100769a33a794385adb62f4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08569511B2;0605;1383225\",\"rsmi\":\"O[C:2](=[O:1])[CH:28]1[CH2:29][CH2:30][N:31]([c:32]2[cH:33][cH:34][n:35][cH:36][cH:37]2)[CH2:38][CH2:39]1.[NH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[c:10](-[c:11]1[n:12][c:13]3[c:14]([cH:15][cH:16][cH:17][cH:18]3)[nH:19]1)[n:20][n:21]2[CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:27]1>CN(C)C=O.ClCCCl.O=C(O)O.On1nnc2ccccc21.[Na+]>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[c:10](-[c:11]1[n:12][c:13]3[c:14]([cH:15][cH:16][cH:17][cH:18]3)[nH:19]1)[n:20][n:21]2[CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:27]1)[CH:28]1[CH2:29][CH2:30][N:31]([c:32]2[cH:33][cH:34][n:35][cH:36][cH:37]2)[CH2:38][CH2:39]1\"},\"mapped_reaction_smiles\":\"O[C:2](=[O:1])[CH:28]1[CH2:29][CH2:30][N:31]([c:32]2[cH:33][cH:34][n:35][cH:36][cH:37]2)[CH2:38][CH2:39]1.[NH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[c:10](-[c:11]1[n:12][c:13]3[c:14]([cH:15][cH:16][cH:17][cH:18]3)[nH:19]1)[n:20][n:21]2[CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:27]1>CN(C)C=O.ClCCCl.O=C(O)O.On1nnc2ccccc21.[Na+]>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[c:10](-[c:11]1[n:12][c:13]3[c:14]([cH:15][cH:16][cH:17][cH:18]3)[nH:19]1)[n:20][n:21]2[CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:27]1)[CH:28]1[CH2:29][CH2:30][N:31]([c:32]2[cH:33][cH:34][n:35][cH:36][cH:37]2)[CH2:38][CH2:39]1\"}",
"reactionStep": {
"id": "sa_7100769a33a794385adb62f4",
"reactionHash": "7d264efb3067d74b12f497dc1e3e6c67d4268c4b02e89cbd196f27b87297adbb"
},
"children": [
{
"id": "6992",
"routeId": "sa_bd9b318cb85c04f8b825ae87",
"moleculeId": "sa_7524e51563de1d898dab8e87",
"parentId": "6991",
"isLeaf": false,
"molecule": {
"id": "sa_7524e51563de1d898dab8e87",
"inchikey": "CWNKQQFEHKASEF-UHFFFAOYSA-N",
"smiles": "Nc1ccc2c(c1)c(-c1nc3ccccc3[nH]1)nn2C1CCCCO1"
},
"smiles": "Nc1ccc2c(c1)c(-c1nc3ccccc3[nH]1)nn2C1CCCCO1",
"reactionStepId": "sa_49d7bc811074e00ca68fad5d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08569511B2;0565;1383205\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8](-[c:9]1[n:10][c:11]3[c:12]([cH:13][cH:14][cH:15][cH:16]3)[nH:17]1)[n:18][n:19]2[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][O:25]1>CCO.[H][H].[Pd]>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8](-[c:9]1[n:10][c:11]3[c:12]([cH:13][cH:14][cH:15][cH:16]3)[nH:17]1)[n:18][n:19]2[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][O:25]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8](-[c:9]1[n:10][c:11]3[c:12]([cH:13][cH:14][cH:15][cH:16]3)[nH:17]1)[n:18][n:19]2[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][O:25]1>CCO.[H][H].[Pd]>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8](-[c:9]1[n:10][c:11]3[c:12]([cH:13][cH:14][cH:15][cH:16]3)[nH:17]1)[n:18][n:19]2[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][O:25]1\"}",
"reactionStep": {
"id": "sa_49d7bc811074e00ca68fad5d",
"reactionHash": "8e9f3d580f233ee1f67fc01ab926f48b83f358a38821d5e8ebc02585d043de6e"
},
"children": [
{
"id": "6993",
"routeId": "sa_bd9b318cb85c04f8b825ae87",
"moleculeId": "sa_8500a4eb60e2d888389ade66",
"parentId": "6992",
"isLeaf": false,
"molecule": {
"id": "sa_8500a4eb60e2d888389ade66",
"inchikey": "NYNFHRGZNABNIB-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc2c(c1)c(-c1nc3ccccc3[nH]1)nn2C1CCCCO1"
},
"smiles": "O=[N+]([O-])c1ccc2c(c1)c(-c1nc3ccccc3[nH]1)nn2C1CCCCO1",
"reactionStepId": "sa_4894d1c7ad6a5391b0051697",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08569511B2;0563;1383204\",\"rsmi\":\"O=[CH:11][c:10]1[c:8]2[c:7]([cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:9]2)[n:21]([CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][O:27]2)[n:20]1.[NH2:12][c:13]1[c:14]([NH2:19])[cH:15][cH:16][cH:17][cH:18]1>C1CCOC1.CCOC(C)=O.Cl.O=S(O)O.[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[c:10](-[c:11]1[n:12][c:13]3[c:14]([cH:15][cH:16][cH:17][cH:18]3)[nH:19]1)[n:20][n:21]2[CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:27]1\"},\"mapped_reaction_smiles\":\"O=[CH:11][c:10]1[c:8]2[c:7]([cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:9]2)[n:21]([CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][O:27]2)[n:20]1.[NH2:12][c:13]1[c:14]([NH2:19])[cH:15][cH:16][cH:17][cH:18]1>C1CCOC1.CCOC(C)=O.Cl.O=S(O)O.[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[c:10](-[c:11]1[n:12][c:13]3[c:14]([cH:15][cH:16][cH:17][cH:18]3)[nH:19]1)[n:20][n:21]2[CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:27]1\"}",
"reactionStep": {
"id": "sa_4894d1c7ad6a5391b0051697",
"reactionHash": "bb28e394843b65b375d8cb8034074fba297632a3e8cb112cc82747359c9c057f"
},
"children": [
{
"id": "6994",
"routeId": "sa_bd9b318cb85c04f8b825ae87",
"moleculeId": "sa_590b79706b6449cb6aa7cc36",
"parentId": "6993",
"isLeaf": true,
"molecule": {
"id": "sa_590b79706b6449cb6aa7cc36",
"inchikey": "GEYOCULIXLDCMW-UHFFFAOYSA-N",
"smiles": "Nc1ccccc1N"
},
"smiles": "Nc1ccccc1N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6995",
"routeId": "sa_bd9b318cb85c04f8b825ae87",
"moleculeId": "sa_87dd535235f9417a7c9a76ba",
"parentId": "6993",
"isLeaf": false,
"molecule": {
"id": "sa_87dd535235f9417a7c9a76ba",
"inchikey": "UCSFZORYXSAROS-UHFFFAOYSA-N",
"smiles": "O=Cc1nn(C2CCCCO2)c2ccc([N+](=O)[O-])cc12"
},
"smiles": "O=Cc1nn(C2CCCCO2)c2ccc([N+](=O)[O-])cc12",
"reactionStepId": "sa_10287d9627e94bb766361def",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08569511B2;0561;1383203\",\"rsmi\":\"[CH:6]1=[CH:7][CH2:8][CH2:9][CH2:10][O:11]1.[O:1]=[CH:2][c:3]1[n:4][nH:5][c:12]2[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]12>C1CCOC1.Cc1ccc(S(=O)(=O)O)cc1.ClCCl>[O:1]=[CH:2][c:3]1[n:4][n:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][O:11]2)[c:12]2[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]12\"},\"mapped_reaction_smiles\":\"[CH:6]1=[CH:7][CH2:8][CH2:9][CH2:10][O:11]1.[O:1]=[CH:2][c:3]1[n:4][nH:5][c:12]2[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]12>C1CCOC1.Cc1ccc(S(=O)(=O)O)cc1.ClCCl>[O:1]=[CH:2][c:3]1[n:4][n:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][O:11]2)[c:12]2[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]12\"}",
"reactionStep": {
"id": "sa_10287d9627e94bb766361def",
"reactionHash": "22df4f9a33a0dee6cc6d544c7c05aec04be2fa321b633605d75fc3e159d0f460"
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"children": [
{
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"routeId": "sa_bd9b318cb85c04f8b825ae87",
"moleculeId": "sa_359472b115a712c065ff6c19",
"parentId": "6995",
"isLeaf": true,
"molecule": {
"id": "sa_359472b115a712c065ff6c19",
"inchikey": "BUDQDWGNQVEFAC-UHFFFAOYSA-N",
"smiles": "C1=COCCC1"
},
"smiles": "C1=COCCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "6997",
"routeId": "sa_bd9b318cb85c04f8b825ae87",
"moleculeId": "sa_2e7b88e5ef056c11238f7c10",
"parentId": "6995",
"isLeaf": true,
"molecule": {
"id": "sa_2e7b88e5ef056c11238f7c10",
"inchikey": "UVUPPLXBIXJRKD-UHFFFAOYSA-N",
"smiles": "O=Cc1n[nH]c2ccc([N+](=O)[O-])cc12"
},
"smiles": "O=Cc1n[nH]c2ccc([N+](=O)[O-])cc12",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
]
},
{
"id": "6998",
"routeId": "sa_bd9b318cb85c04f8b825ae87",
"moleculeId": "sa_a4f6bd1be04e639c5b66b65b",
"parentId": "6991",
"isLeaf": true,
"molecule": {
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"inchikey": "UISWRUUBFFHGLE-UHFFFAOYSA-N",
"smiles": "O=C(O)C1CCN(c2ccncc2)CC1"
},
"smiles": "O=C(O)C1CCN(c2ccncc2)CC1",
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}
]
}
]
}
}