Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN1CCN(C(=O)Nc2nc3ccccc3s2)c2cc(-c3cccc(C(=O)O)n3)ccc21
InChiKey
HRNHYKJWRGNWJS-UHFFFAOYSA-N
Route Signature
5a0c7bc4826fd8bdcc8fca011917c2744fd6a6f4a29d0dffa7d637b61431ea6a
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_e95f7d109f2d8b118896fc62",
"signature": "5a0c7bc4826fd8bdcc8fca011917c2744fd6a6f4a29d0dffa7d637b61431ea6a",
"contentHash": "6275d7bc76b9c41da01cffdbef72e4e38c85d9fc0483daf95793573d578c2291",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_32e32b33c81320afeaca19b3",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-04804",
"moleculeId": "sa_e91382788a8c4ca65ecc1294",
"smiles": "CN1CCN(C(=O)Nc2nc3ccccc3s2)c2cc(-c3cccc(C(=O)O)n3)ccc21",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_e91382788a8c4ca65ecc1294",
"inchikey": "HRNHYKJWRGNWJS-UHFFFAOYSA-N",
"smiles": "CN1CCN(C(=O)Nc2nc3ccccc3s2)c2cc(-c3cccc(C(=O)O)n3)ccc21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "2654",
"routeId": "sa_e95f7d109f2d8b118896fc62",
"moleculeId": "sa_e91382788a8c4ca65ecc1294",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_e91382788a8c4ca65ecc1294",
"inchikey": "HRNHYKJWRGNWJS-UHFFFAOYSA-N",
"smiles": "CN1CCN(C(=O)Nc2nc3ccccc3s2)c2cc(-c3cccc(C(=O)O)n3)ccc21"
},
"smiles": "CN1CCN(C(=O)Nc2nc3ccccc3s2)c2cc(-c3cccc(C(=O)O)n3)ccc21",
"reactionStepId": "sa_40a43460168440191b384df2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140005190A1;0314;1468326\",\"rsmi\":\"CC(C)(C)[O:28][C:26]([c:25]1[cH:24][cH:23][cH:22][c:21](-[c:20]2[cH:19][c:18]3[c:32]([cH:31][cH:30]2)[N:2]([CH3:1])[CH2:3][CH2:4][N:5]3[C:6](=[O:7])[NH:8][c:9]2[n:10][c:11]3[c:12]([cH:13][cH:14][cH:15][cH:16]3)[s:17]2)[n:29]1)=[O:27]>ClCCl.O=C(O)C(F)(F)F>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[n:10][c:11]3[c:12]([cH:13][cH:14][cH:15][cH:16]3)[s:17]2)[c:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][c:25]([C:26](=[O:27])[OH:28])[n:29]3)[cH:30][cH:31][c:32]21\"},\"mapped_reaction_smiles\":\"CC(C)(C)[O:28][C:26]([c:25]1[cH:24][cH:23][cH:22][c:21](-[c:20]2[cH:19][c:18]3[c:32]([cH:31][cH:30]2)[N:2]([CH3:1])[CH2:3][CH2:4][N:5]3[C:6](=[O:7])[NH:8][c:9]2[n:10][c:11]3[c:12]([cH:13][cH:14][cH:15][cH:16]3)[s:17]2)[n:29]1)=[O:27]>ClCCl.O=C(O)C(F)(F)F>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[n:10][c:11]3[c:12]([cH:13][cH:14][cH:15][cH:16]3)[s:17]2)[c:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][c:25]([C:26](=[O:27])[OH:28])[n:29]3)[cH:30][cH:31][c:32]21\"}",
"reactionStep": {
"id": "sa_40a43460168440191b384df2",
"reactionHash": "2dbfd5bf9a2e829f95c19d3a8f2e503cfc5f26b381653e245b86e355edf83c12"
},
"children": [
{
"id": "2655",
"routeId": "sa_e95f7d109f2d8b118896fc62",
"moleculeId": "sa_3e3a2cf6cffc2123062ad954",
"parentId": "2654",
"isLeaf": false,
"molecule": {
"id": "sa_3e3a2cf6cffc2123062ad954",
"inchikey": "VBKGKBRYDSMPLN-UHFFFAOYSA-N",
"smiles": "CN1CCN(C(=O)Nc2nc3ccccc3s2)c2cc(-c3cccc(C(=O)OC(C)(C)C)n3)ccc21"
},
"smiles": "CN1CCN(C(=O)Nc2nc3ccccc3s2)c2cc(-c3cccc(C(=O)OC(C)(C)C)n3)ccc21",
"reactionStepId": "sa_f316e3a9347372bc7d8ee4f1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140005190A1;0312;1468325\",\"rsmi\":\"O=[N+]([O-])c1ccc(O[C:6](=[O:7])[NH:8][c:9]2[n:10][c:11]3[c:12]([cH:13][cH:14][cH:15][cH:16]3)[s:17]2)cc1.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][c:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][c:25]([C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[n:33]3)[cH:34][cH:35][c:36]21>CC#N>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[n:10][c:11]3[c:12]([cH:13][cH:14][cH:15][cH:16]3)[s:17]2)[c:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][c:25]([C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[n:33]3)[cH:34][cH:35][c:36]21\"},\"mapped_reaction_smiles\":\"O=[N+]([O-])c1ccc(O[C:6](=[O:7])[NH:8][c:9]2[n:10][c:11]3[c:12]([cH:13][cH:14][cH:15][cH:16]3)[s:17]2)cc1.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][c:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][c:25]([C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[n:33]3)[cH:34][cH:35][c:36]21>CC#N>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[NH:8][c:9]2[n:10][c:11]3[c:12]([cH:13][cH:14][cH:15][cH:16]3)[s:17]2)[c:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][c:25]([C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[n:33]3)[cH:34][cH:35][c:36]21\"}",
"reactionStep": {
"id": "sa_f316e3a9347372bc7d8ee4f1",
"reactionHash": "e3aad76afbbd3796b41dfbb959bfc74debef479c10ea867311832002e3c03c25"
},
"children": [
{
"id": "2656",
"routeId": "sa_e95f7d109f2d8b118896fc62",
"moleculeId": "sa_15426d77d260213beef8c342",
"parentId": "2655",
"isLeaf": false,
"molecule": {
"id": "sa_15426d77d260213beef8c342",
"inchikey": "DBABIXUKZSGKDY-UHFFFAOYSA-N",
"smiles": "CN1CCNc2cc(-c3cccc(C(=O)OC(C)(C)C)n3)ccc21"
},
"smiles": "CN1CCNc2cc(-c3cccc(C(=O)OC(C)(C)C)n3)ccc21",
"reactionStepId": "sa_8356549dab07ecb2e385b6eb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140005190A1;0310;1468324\",\"rsmi\":\"Br[c:9]1[cH:10][cH:11][cH:12][c:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[n:21]1.CC1(C)OB([c:8]2[cH:7][c:6]3[c:24]([cH:23][cH:22]2)[N:2]([CH3:1])[CH2:3][CH2:4][NH:5]3)OC1(C)C>C1COCCO1.CCCC[N+](CCCC)(CCCC)CCCC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=C(O)O.Br.[K+].[K+]>[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][c:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[n:21]3)[cH:22][cH:23][c:24]21\"},\"mapped_reaction_smiles\":\"Br[c:9]1[cH:10][cH:11][cH:12][c:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[n:21]1.CC1(C)OB([c:8]2[cH:7][c:6]3[c:24]([cH:23][cH:22]2)[N:2]([CH3:1])[CH2:3][CH2:4][NH:5]3)OC1(C)C>C1COCCO1.CCCC[N+](CCCC)(CCCC)CCCC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=C(O)O.Br.[K+].[K+]>[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][c:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[n:21]3)[cH:22][cH:23][c:24]21\"}",
"reactionStep": {
"id": "sa_8356549dab07ecb2e385b6eb",
"reactionHash": "3505bcb82435503ebc26a799df495e484c73d1f70b2b11da0011e08dc6a7c39a"
},
"children": [
{
"id": "2657",
"routeId": "sa_e95f7d109f2d8b118896fc62",
"moleculeId": "sa_cab0321948e9d5c99784d391",
"parentId": "2656",
"isLeaf": true,
"molecule": {
"id": "sa_cab0321948e9d5c99784d391",
"inchikey": "FMFVWFOLGYTRBX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)c1cccc(Br)n1"
},
"smiles": "CC(C)(C)OC(=O)c1cccc(Br)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2658",
"routeId": "sa_e95f7d109f2d8b118896fc62",
"moleculeId": "sa_81ee2b46bea8b90f52bde16f",
"parentId": "2656",
"isLeaf": false,
"molecule": {
"id": "sa_81ee2b46bea8b90f52bde16f",
"inchikey": "HXXLPGXGDMRSRV-UHFFFAOYSA-N",
"smiles": "CN1CCNc2cc(B3OC(C)(C)C(C)(C)O3)ccc21"
},
"smiles": "CN1CCNc2cc(B3OC(C)(C)C(C)(C)O3)ccc21",
"reactionStepId": "sa_9457d0a7ac61e9d15334b309",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140005190A1;0308;1468323\",\"rsmi\":\"Br[c:8]1[cH:7][c:6]2[c:20]([cH:19][cH:18]1)[N:2]([CH3:1])[CH2:3][CH2:4][NH:5]2.CC1(C)OB([B:9]2[O:10][C:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[O:17]2)OC1(C)C>C1COCCO1.CC(=O)O.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[K+].[Pd].[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][c:6]2[cH:7][c:8]([B:9]3[O:10][C:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[O:17]3)[cH:18][cH:19][c:20]21\"},\"mapped_reaction_smiles\":\"Br[c:8]1[cH:7][c:6]2[c:20]([cH:19][cH:18]1)[N:2]([CH3:1])[CH2:3][CH2:4][NH:5]2.CC1(C)OB([B:9]2[O:10][C:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[O:17]2)OC1(C)C>C1COCCO1.CC(=O)O.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[K+].[Pd].[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][c:6]2[cH:7][c:8]([B:9]3[O:10][C:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[O:17]3)[cH:18][cH:19][c:20]21\"}",
"reactionStep": {
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"reactionHash": "b26d5b5e7a46bd6f1e94506d3b15fc8b1bb11703ac9c5144fb7dd6e25ecc27ec"
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"children": [
{
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"routeId": "sa_e95f7d109f2d8b118896fc62",
"moleculeId": "sa_8f1b843bd763e99afcb1d554",
"parentId": "2658",
"isLeaf": true,
"molecule": {
"id": "sa_8f1b843bd763e99afcb1d554",
"inchikey": "DXGACWBAFPNXOZ-UHFFFAOYSA-N",
"smiles": "CN1CCNc2cc(Br)ccc21"
},
"smiles": "CN1CCNc2cc(Br)ccc21",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "2660",
"routeId": "sa_e95f7d109f2d8b118896fc62",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "2658",
"isLeaf": true,
"molecule": {
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"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
},
{
"id": "2661",
"routeId": "sa_e95f7d109f2d8b118896fc62",
"moleculeId": "sa_7fa40a027a38728e0c65e5a0",
"parentId": "2655",
"isLeaf": false,
"molecule": {
"id": "sa_7fa40a027a38728e0c65e5a0",
"inchikey": "UJMXBOVAORPTKW-UHFFFAOYSA-N",
"smiles": "O=C(Nc1nc2ccccc2s1)Oc1ccc([N+](=O)[O-])cc1"
},
"smiles": "O=C(Nc1nc2ccccc2s1)Oc1ccc([N+](=O)[O-])cc1",
"reactionStepId": "sa_d825674b401a1e5806e00cba",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140005190A1;0243;1468301\",\"rsmi\":\"Cl[C:2](=[O:1])[O:13][c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1.[NH2:3][c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[s:12]1>ClCCl.c1ccncc1>[O:1]=[C:2]([NH:3][c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[s:12]1)[O:13][c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[O:13][c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1.[NH2:3][c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[s:12]1>ClCCl.c1ccncc1>[O:1]=[C:2]([NH:3][c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[s:12]1)[O:13][c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1\"}",
"reactionStep": {
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"children": [
{
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},
"smiles": "O=C(Cl)Oc1ccc([N+](=O)[O-])cc1",
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{
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"molecule": {
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"inchikey": "UHGULLIUJBCTEF-UHFFFAOYSA-N",
"smiles": "N=c1[nH]c2ccccc2s1"
},
"smiles": "Nc1nc2ccccc2s1",
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}
]
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]
}
]
}
}