Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CNC(=O)c1cccc2nc(-c3cc(-c4cnn(C5CCNCC5)c4)cnc3N)oc12
InChiKey
VXIKBIZXMSEUBY-UHFFFAOYSA-N
Route Signature
553ff8ecd277e56ed9082b56cd9c16ff5f2cdd1a79513afdbe371493aa53fd1b
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_3e4fd923e11f893358888088",
"signature": "553ff8ecd277e56ed9082b56cd9c16ff5f2cdd1a79513afdbe371493aa53fd1b",
"contentHash": "4623b76cd5e123fb7c852e118b0a5ecc77bc13b4b666c79f33f5c5e8d3cb536a",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_001a25606737f8b2ba53d1cb",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01658",
"moleculeId": "sa_f6237dac5d288ac4af4a1361",
"smiles": "CNC(=O)c1cccc2nc(-c3cc(-c4cnn(C5CCNCC5)c4)cnc3N)oc12",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_f6237dac5d288ac4af4a1361",
"inchikey": "VXIKBIZXMSEUBY-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1cccc2nc(-c3cc(-c4cnn(C5CCNCC5)c4)cnc3N)oc12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14465",
"routeId": "sa_3e4fd923e11f893358888088",
"moleculeId": "sa_f6237dac5d288ac4af4a1361",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f6237dac5d288ac4af4a1361",
"inchikey": "VXIKBIZXMSEUBY-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1cccc2nc(-c3cc(-c4cnn(C5CCNCC5)c4)cnc3N)oc12"
},
"smiles": "CNC(=O)c1cccc2nc(-c3cc(-c4cnn(C5CCNCC5)c4)cnc3N)oc12",
"reactionStepId": "sa_cfea772fda15c4fca42c27d2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118305A1;1435;701112\",\"rsmi\":\"CC(C)(C)OC(=O)[N:22]1[CH2:21][CH2:20][CH:19]([n:18]2[cH:17][c:16](-[c:15]3[cH:14][c:13](-[c:12]4[o:11][c:10]5[c:5]([C:3]([NH:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][c:9]5[n:31]4)[c:29]([NH2:30])[n:28][cH:27]3)[cH:26][n:25]2)[CH2:24][CH2:23]1>CC(C)O.Cl>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[o:11][c:12](-[c:13]1[cH:14][c:15](-[c:16]3[cH:17][n:18]([CH:19]4[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]4)[n:25][cH:26]3)[cH:27][n:28][c:29]1[NH2:30])[n:31]2\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:22]1[CH2:21][CH2:20][CH:19]([n:18]2[cH:17][c:16](-[c:15]3[cH:14][c:13](-[c:12]4[o:11][c:10]5[c:5]([C:3]([NH:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][c:9]5[n:31]4)[c:29]([NH2:30])[n:28][cH:27]3)[cH:26][n:25]2)[CH2:24][CH2:23]1>CC(C)O.Cl>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[o:11][c:12](-[c:13]1[cH:14][c:15](-[c:16]3[cH:17][n:18]([CH:19]4[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]4)[n:25][cH:26]3)[cH:27][n:28][c:29]1[NH2:30])[n:31]2\"}",
"reactionStep": {
"id": "sa_cfea772fda15c4fca42c27d2",
"reactionHash": "427f3950e79713726d102f57c337af0b8f82d3e422fa73fe639cf7b35bc5c3f7"
},
"children": [
{
"id": "14466",
"routeId": "sa_3e4fd923e11f893358888088",
"moleculeId": "sa_3bc599cab8415e187141256e",
"parentId": "14465",
"isLeaf": false,
"molecule": {
"id": "sa_3bc599cab8415e187141256e",
"inchikey": "YNYJGTNPBBAJNV-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1cccc2nc(-c3cc(-c4cnn(C5CCN(C(=O)OC(C)(C)C)CC5)c4)cnc3N)oc12"
},
"smiles": "CNC(=O)c1cccc2nc(-c3cc(-c4cnn(C5CCN(C(=O)OC(C)(C)C)CC5)c4)cnc3N)oc12",
"reactionStepId": "sa_6fe3ed2c024b0dadae069a07",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118305A1;1439;701114\",\"rsmi\":\"O[C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[o:11][c:12](-[c:13]1[c:14]([NH2:15])[n:16][cH:17][c:18](-[c:19]3[cH:20][n:21]([CH:22]4[CH2:23][CH2:24][N:25]([C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:33][CH2:34]4)[n:35][cH:36]3)[cH:37]1)[n:38]2.[CH3:1][NH2:2]>CN(C)C(=[O+]n1nnc2cccnc21)N(C)C.CN(C)C=O.CO.F[PH](F)(F)(F)(F)F>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[o:11][c:12](-[c:13]1[c:14]([NH2:15])[n:16][cH:17][c:18](-[c:19]3[cH:20][n:21]([CH:22]4[CH2:23][CH2:24][N:25]([C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:33][CH2:34]4)[n:35][cH:36]3)[cH:37]1)[n:38]2\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[o:11][c:12](-[c:13]1[c:14]([NH2:15])[n:16][cH:17][c:18](-[c:19]3[cH:20][n:21]([CH:22]4[CH2:23][CH2:24][N:25]([C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:33][CH2:34]4)[n:35][cH:36]3)[cH:37]1)[n:38]2.[CH3:1][NH2:2]>CN(C)C(=[O+]n1nnc2cccnc21)N(C)C.CN(C)C=O.CO.F[PH](F)(F)(F)(F)F>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[o:11][c:12](-[c:13]1[c:14]([NH2:15])[n:16][cH:17][c:18](-[c:19]3[cH:20][n:21]([CH:22]4[CH2:23][CH2:24][N:25]([C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:33][CH2:34]4)[n:35][cH:36]3)[cH:37]1)[n:38]2\"}",
"reactionStep": {
"id": "sa_6fe3ed2c024b0dadae069a07",
"reactionHash": "361f885796ba3390eac338393da057af1c3d69a7669c5a7e6fcf2bc91b5b1c14"
},
"children": [
{
"id": "14467",
"routeId": "sa_3e4fd923e11f893358888088",
"moleculeId": "sa_e00cdbb7fb9d3ecf114a19d3",
"parentId": "14466",
"isLeaf": true,
"molecule": {
"id": "sa_e00cdbb7fb9d3ecf114a19d3",
"inchikey": "BAVYZALUXZFZLV-UHFFFAOYSA-N",
"smiles": "CN"
},
"smiles": "CN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14468",
"routeId": "sa_3e4fd923e11f893358888088",
"moleculeId": "sa_462fa26d32a6faeea688fa9b",
"parentId": "14466",
"isLeaf": false,
"molecule": {
"id": "sa_462fa26d32a6faeea688fa9b",
"inchikey": "JOTJLZUUTAZFCK-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(n2cc(-c3cnc(N)c(-c4nc5cccc(C(=O)O)c5o4)c3)cn2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(n2cc(-c3cnc(N)c(-c4nc5cccc(C(=O)O)c5o4)c3)cn2)CC1",
"reactionStepId": "sa_54192c0ea871821859c7fe12",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118305A1;1438;701113\",\"rsmi\":\"C[O:29][C:27]([c:26]1[c:24]2[c:23]([n:22][c:21](-[c:20]3[c:18]([NH2:19])[n:17][cH:16][c:15](-[c:14]4[cH:13][n:12]([CH:11]5[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:37][CH2:36]5)[n:35][cH:34]4)[cH:33]3)[o:25]2)[cH:32][cH:31][cH:30]1)=[O:28]>CO.[Na+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([n:12]2[cH:13][c:14](-[c:15]3[cH:16][n:17][c:18]([NH2:19])[c:20](-[c:21]4[n:22][c:23]5[c:24]([o:25]4)[c:26]([C:27](=[O:28])[OH:29])[cH:30][cH:31][cH:32]5)[cH:33]3)[cH:34][n:35]2)[CH2:36][CH2:37]1\"},\"mapped_reaction_smiles\":\"C[O:29][C:27]([c:26]1[c:24]2[c:23]([n:22][c:21](-[c:20]3[c:18]([NH2:19])[n:17][cH:16][c:15](-[c:14]4[cH:13][n:12]([CH:11]5[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:37][CH2:36]5)[n:35][cH:34]4)[cH:33]3)[o:25]2)[cH:32][cH:31][cH:30]1)=[O:28]>CO.[Na+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([n:12]2[cH:13][c:14](-[c:15]3[cH:16][n:17][c:18]([NH2:19])[c:20](-[c:21]4[n:22][c:23]5[c:24]([o:25]4)[c:26]([C:27](=[O:28])[OH:29])[cH:30][cH:31][cH:32]5)[cH:33]3)[cH:34][n:35]2)[CH2:36][CH2:37]1\"}",
"reactionStep": {
"id": "sa_54192c0ea871821859c7fe12",
"reactionHash": "af175eb6c784e555e80a84b82c686b5b47ecd6522d027ff774ef272e543bb6a4"
},
"children": [
{
"id": "14469",
"routeId": "sa_3e4fd923e11f893358888088",
"moleculeId": "sa_f52aa2d4f0ca261b6c979ae4",
"parentId": "14468",
"isLeaf": false,
"molecule": {
"id": "sa_f52aa2d4f0ca261b6c979ae4",
"inchikey": "VQTMMAYSLBADEH-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cccc2nc(-c3cc(-c4cnn(C5CCN(C(=O)OC(C)(C)C)CC5)c4)cnc3N)oc12"
},
"smiles": "COC(=O)c1cccc2nc(-c3cc(-c4cnn(C5CCN(C(=O)OC(C)(C)C)CC5)c4)cnc3N)oc12",
"reactionStepId": "sa_3e1755c1fe02cc08408502be",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118305A1;1422;701107\",\"rsmi\":\"Br[c:15]1[cH:14][c:13](-[c:12]2[o:11][c:10]3[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][c:9]3[n:38]2)[c:36]([NH2:37])[n:35][cH:34]1.CC1(C)OB([c:16]2[cH:17][n:18]([CH:19]3[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]3)[n:32][cH:33]2)OC1(C)C>CO.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cs+].F>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[o:11][c:12](-[c:13]1[cH:14][c:15](-[c:16]3[cH:17][n:18]([CH:19]4[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]4)[n:32][cH:33]3)[cH:34][n:35][c:36]1[NH2:37])[n:38]2\"},\"mapped_reaction_smiles\":\"Br[c:15]1[cH:14][c:13](-[c:12]2[o:11][c:10]3[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][c:9]3[n:38]2)[c:36]([NH2:37])[n:35][cH:34]1.CC1(C)OB([c:16]2[cH:17][n:18]([CH:19]3[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]3)[n:32][cH:33]2)OC1(C)C>CO.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cs+].F>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[o:11][c:12](-[c:13]1[cH:14][c:15](-[c:16]3[cH:17][n:18]([CH:19]4[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]4)[n:32][cH:33]3)[cH:34][n:35][c:36]1[NH2:37])[n:38]2\"}",
"reactionStep": {
"id": "sa_3e1755c1fe02cc08408502be",
"reactionHash": "1715c745d9c19e03b2359a4546f323be51c3c183c89b58674121f009f5855aa3"
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"children": [
{
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"routeId": "sa_3e4fd923e11f893358888088",
"moleculeId": "sa_ff9f9ed27807258e40cc65a6",
"parentId": "14469",
"isLeaf": false,
"molecule": {
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"inchikey": "DLXNRZKEPZAMCL-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cccc2nc(-c3cc(Br)cnc3N)oc12"
},
"smiles": "COC(=O)c1cccc2nc(-c3cc(Br)cnc3N)oc12",
"reactionStepId": "sa_ded249f18f7a2e3776356eb3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118305A1;1421;701106\",\"rsmi\":\"O=C1CCC(=O)N1[Br:16].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[o:11][c:12](-[c:13]1[cH:14][cH:15][cH:17][n:18][c:19]1[NH2:20])[n:21]2>C1CCOC1.ClC(Cl)Cl.N>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[o:11][c:12](-[c:13]1[cH:14][c:15]([Br:16])[cH:17][n:18][c:19]1[NH2:20])[n:21]2\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:16].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[o:11][c:12](-[c:13]1[cH:14][cH:15][cH:17][n:18][c:19]1[NH2:20])[n:21]2>C1CCOC1.ClC(Cl)Cl.N>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[o:11][c:12](-[c:13]1[cH:14][c:15]([Br:16])[cH:17][n:18][c:19]1[NH2:20])[n:21]2\"}",
"reactionStep": {
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"children": [
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"molecule": {
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"smiles": "COC(=O)c1cccc2nc(-c3cccnc3N)oc12"
},
"smiles": "COC(=O)c1cccc2nc(-c3cccnc3N)oc12",
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},
{
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"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
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}
]
},
{
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"smiles": "CC(C)(C)OC(=O)N1CCC(n2cc(B3OC(C)(C)C(C)(C)O3)cn2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(n2cc(B3OC(C)(C)C(C)(C)O3)cn2)CC1",
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}
]
}
]
}
]
}
]
}
}