Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(O)Cn1nnc(-c2cnc(N3CCC(Oc4cc(Cl)ccc4Cl)CC3)nc2)n1
InChiKey
NQCBJQSDOCQVJI-UHFFFAOYSA-N
Route Signature
62e78fde95c6cad14330984021345118853ce7bec15b870c6ed7bc4d829ee9e6
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_1505ce0530c156198652764f",
"signature": "62e78fde95c6cad14330984021345118853ce7bec15b870c6ed7bc4d829ee9e6",
"contentHash": "191e1b67ae70397d23fe39ce565f9604aab9b384fead4dcba733a5293ef682f7",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_2306ce113ac42387465a71e3",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00392",
"moleculeId": "sa_3b00c8ba2b0002d4695d653c",
"smiles": "O=C(O)Cn1nnc(-c2cnc(N3CCC(Oc4cc(Cl)ccc4Cl)CC3)nc2)n1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_3b00c8ba2b0002d4695d653c",
"inchikey": "NQCBJQSDOCQVJI-UHFFFAOYSA-N",
"smiles": "O=C(O)Cn1nnc(-c2cnc(N3CCC(Oc4cc(Cl)ccc4Cl)CC3)nc2)n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13168",
"routeId": "sa_1505ce0530c156198652764f",
"moleculeId": "sa_3b00c8ba2b0002d4695d653c",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_3b00c8ba2b0002d4695d653c",
"inchikey": "NQCBJQSDOCQVJI-UHFFFAOYSA-N",
"smiles": "O=C(O)Cn1nnc(-c2cnc(N3CCC(Oc4cc(Cl)ccc4Cl)CC3)nc2)n1"
},
"smiles": "O=C(O)Cn1nnc(-c2cnc(N3CCC(Oc4cc(Cl)ccc4Cl)CC3)nc2)n1",
"reactionStepId": "sa_8369cb0b1521e07b6f09a846",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090270434A1;0283;782116\",\"rsmi\":\"CC[O:3][C:2](=[O:1])[CH2:4][n:5]1[n:6][n:7][c:8](-[c:9]2[cH:10][n:11][c:12]([N:13]3[CH2:14][CH2:15][CH:16]([O:17][c:18]4[c:19]([Cl:20])[cH:21][cH:22][c:23]([Cl:24])[cH:25]4)[CH2:26][CH2:27]3)[n:28][cH:29]2)[n:30]1>[Na+].O>[O:1]=[C:2]([OH:3])[CH2:4][n:5]1[n:6][n:7][c:8](-[c:9]2[cH:10][n:11][c:12]([N:13]3[CH2:14][CH2:15][CH:16]([O:17][c:18]4[c:19]([Cl:20])[cH:21][cH:22][c:23]([Cl:24])[cH:25]4)[CH2:26][CH2:27]3)[n:28][cH:29]2)[n:30]1\"},\"mapped_reaction_smiles\":\"CC[O:3][C:2](=[O:1])[CH2:4][n:5]1[n:6][n:7][c:8](-[c:9]2[cH:10][n:11][c:12]([N:13]3[CH2:14][CH2:15][CH:16]([O:17][c:18]4[c:19]([Cl:20])[cH:21][cH:22][c:23]([Cl:24])[cH:25]4)[CH2:26][CH2:27]3)[n:28][cH:29]2)[n:30]1>[Na+].O>[O:1]=[C:2]([OH:3])[CH2:4][n:5]1[n:6][n:7][c:8](-[c:9]2[cH:10][n:11][c:12]([N:13]3[CH2:14][CH2:15][CH:16]([O:17][c:18]4[c:19]([Cl:20])[cH:21][cH:22][c:23]([Cl:24])[cH:25]4)[CH2:26][CH2:27]3)[n:28][cH:29]2)[n:30]1\"}",
"reactionStep": {
"id": "sa_8369cb0b1521e07b6f09a846",
"reactionHash": "9772234db4b2f0ce1424da826bab8ecd2403c014ece140b05d3882390d70c24a"
},
"children": [
{
"id": "13169",
"routeId": "sa_1505ce0530c156198652764f",
"moleculeId": "sa_f2cb6aa8ee13d23d358b9347",
"parentId": "13168",
"isLeaf": false,
"molecule": {
"id": "sa_f2cb6aa8ee13d23d358b9347",
"inchikey": "JPLHDRNMJZIXMW-UHFFFAOYSA-N",
"smiles": "CCOC(=O)Cn1nnc(-c2cnc(N3CCC(Oc4cc(Cl)ccc4Cl)CC3)nc2)n1"
},
"smiles": "CCOC(=O)Cn1nnc(-c2cnc(N3CCC(Oc4cc(Cl)ccc4Cl)CC3)nc2)n1",
"reactionStepId": "sa_a8d07608be4b7774f3363054",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090270434A1;0282;782115\",\"rsmi\":\"O[c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([Cl:26])[cH:27]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[n:8][n:9][c:10](-[c:11]2[cH:12][n:13][c:14]([N:15]3[CH2:16][CH2:17][CH:18]([OH:19])[CH2:28][CH2:29]3)[n:30][cH:31]2)[n:32]1>CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[n:8][n:9][c:10](-[c:11]2[cH:12][n:13][c:14]([N:15]3[CH2:16][CH2:17][CH:18]([O:19][c:20]4[c:21]([Cl:22])[cH:23][cH:24][c:25]([Cl:26])[cH:27]4)[CH2:28][CH2:29]3)[n:30][cH:31]2)[n:32]1\"},\"mapped_reaction_smiles\":\"O[c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([Cl:26])[cH:27]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[n:8][n:9][c:10](-[c:11]2[cH:12][n:13][c:14]([N:15]3[CH2:16][CH2:17][CH:18]([OH:19])[CH2:28][CH2:29]3)[n:30][cH:31]2)[n:32]1>CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[n:8][n:9][c:10](-[c:11]2[cH:12][n:13][c:14]([N:15]3[CH2:16][CH2:17][CH:18]([O:19][c:20]4[c:21]([Cl:22])[cH:23][cH:24][c:25]([Cl:26])[cH:27]4)[CH2:28][CH2:29]3)[n:30][cH:31]2)[n:32]1\"}",
"reactionStep": {
"id": "sa_a8d07608be4b7774f3363054",
"reactionHash": "411ef90c5bbdf87ada2f91be7331467736d5da876b94059369d2af6bb65735d0"
},
"children": [
{
"id": "13170",
"routeId": "sa_1505ce0530c156198652764f",
"moleculeId": "sa_b2eb7462694c5e34aaeb66fd",
"parentId": "13169",
"isLeaf": true,
"molecule": {
"id": "sa_b2eb7462694c5e34aaeb66fd",
"inchikey": "RANCECPPZPIPNO-UHFFFAOYSA-N",
"smiles": "Oc1cc(Cl)ccc1Cl"
},
"smiles": "Oc1cc(Cl)ccc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13171",
"routeId": "sa_1505ce0530c156198652764f",
"moleculeId": "sa_fd4a737b2b37d7d188654fa4",
"parentId": "13169",
"isLeaf": false,
"molecule": {
"id": "sa_fd4a737b2b37d7d188654fa4",
"inchikey": "VKBHFKFATHHFHV-UHFFFAOYSA-N",
"smiles": "CCOC(=O)Cn1nnc(-c2cnc(N3CCC(O)CC3)nc2)n1"
},
"smiles": "CCOC(=O)Cn1nnc(-c2cnc(N3CCC(O)CC3)nc2)n1",
"reactionStepId": "sa_a519f4dfdc77ad8f663b0db4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090270434A1;0267;782112\",\"rsmi\":\"Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[n:7]1[n:8][nH:9][c:10](-[c:11]2[cH:12][n:13][c:14]([N:15]3[CH2:16][CH2:17][CH:18]([OH:19])[CH2:20][CH2:21]3)[n:22][cH:23]2)[n:24]1>C1CCOC1.CCN(CC)CC>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[n:8][n:9][c:10](-[c:11]2[cH:12][n:13][c:14]([N:15]3[CH2:16][CH2:17][CH:18]([OH:19])[CH2:20][CH2:21]3)[n:22][cH:23]2)[n:24]1\"},\"mapped_reaction_smiles\":\"Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[n:7]1[n:8][nH:9][c:10](-[c:11]2[cH:12][n:13][c:14]([N:15]3[CH2:16][CH2:17][CH:18]([OH:19])[CH2:20][CH2:21]3)[n:22][cH:23]2)[n:24]1>C1CCOC1.CCN(CC)CC>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[n:8][n:9][c:10](-[c:11]2[cH:12][n:13][c:14]([N:15]3[CH2:16][CH2:17][CH:18]([OH:19])[CH2:20][CH2:21]3)[n:22][cH:23]2)[n:24]1\"}",
"reactionStep": {
"id": "sa_a519f4dfdc77ad8f663b0db4",
"reactionHash": "6fd43684eff9e73ea12bd25d095cf6446ce9116336d96573fd3e98a3b3a9ab1d"
},
"children": [
{
"id": "13172",
"routeId": "sa_1505ce0530c156198652764f",
"moleculeId": "sa_472fec9358a47312e142df1b",
"parentId": "13171",
"isLeaf": false,
"molecule": {
"id": "sa_472fec9358a47312e142df1b",
"inchikey": "JLUSFQZSKNKMKO-UHFFFAOYSA-N",
"smiles": "OC1CCN(c2ncc(-c3nnn[nH]3)cn2)CC1"
},
"smiles": "OC1CCN(c2ncc(-c3nnn[nH]3)cn2)CC1",
"reactionStepId": "sa_13fdf5ee17f53ea4a7db6f1c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090270434A1;0265;782111\",\"rsmi\":\"[N+:12](=[N-:13])=[N-:14].[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][c:9]([C:10]#[N:11])[cH:15][n:16]2)[CH2:17][CH2:18]1>CN(C)C=O.Cl.N.[Na+].[Na+].O>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][c:9](-[c:10]3[n:11][n:12][n:13][nH:14]3)[cH:15][n:16]2)[CH2:17][CH2:18]1\"},\"mapped_reaction_smiles\":\"[N+:12](=[N-:13])=[N-:14].[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][c:9]([C:10]#[N:11])[cH:15][n:16]2)[CH2:17][CH2:18]1>CN(C)C=O.Cl.N.[Na+].[Na+].O>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][c:9](-[c:10]3[n:11][n:12][n:13][nH:14]3)[cH:15][n:16]2)[CH2:17][CH2:18]1\"}",
"reactionStep": {
"id": "sa_13fdf5ee17f53ea4a7db6f1c",
"reactionHash": "2cbf06bd69ba92f477d92667e618ae00a31487f1fe1b952658f2c4c3af28e548"
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"children": [
{
"id": "13173",
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"moleculeId": "sa_50a8f83dd89c267fbada1205",
"parentId": "13172",
"isLeaf": true,
"molecule": {
"id": "sa_50a8f83dd89c267fbada1205",
"inchikey": "IVRMZWNICZWHMI-UHFFFAOYSA-N",
"smiles": "[N]N=[N-]"
},
"smiles": "[N-]=[N+]=[N-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13174",
"routeId": "sa_1505ce0530c156198652764f",
"moleculeId": "sa_0b856c4c87a5230ec92d4d88",
"parentId": "13172",
"isLeaf": false,
"molecule": {
"id": "sa_0b856c4c87a5230ec92d4d88",
"inchikey": "MRFRSDSXKGTWQB-UHFFFAOYSA-N",
"smiles": "N#Cc1cnc(N2CCC(O)CC2)nc1"
},
"smiles": "N#Cc1cnc(N2CCC(O)CC2)nc1",
"reactionStepId": "sa_5a082ad39dd0e236bf6ea6ed",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090270434A1;0263;782110\",\"rsmi\":\"Br[c:3]1[cH:4][n:5][c:6]([N:7]2[CH2:8][CH2:9][CH:10]([OH:11])[CH2:12][CH2:13]2)[n:14][cH:15]1.[Cu][C:2]#[N:1]>CCOC(C)=O.CN(C)C=O.O>[N:1]#[C:2][c:3]1[cH:4][n:5][c:6]([N:7]2[CH2:8][CH2:9][CH:10]([OH:11])[CH2:12][CH2:13]2)[n:14][cH:15]1\"},\"mapped_reaction_smiles\":\"Br[c:3]1[cH:4][n:5][c:6]([N:7]2[CH2:8][CH2:9][CH:10]([OH:11])[CH2:12][CH2:13]2)[n:14][cH:15]1.[Cu][C:2]#[N:1]>CCOC(C)=O.CN(C)C=O.O>[N:1]#[C:2][c:3]1[cH:4][n:5][c:6]([N:7]2[CH2:8][CH2:9][CH:10]([OH:11])[CH2:12][CH2:13]2)[n:14][cH:15]1\"}",
"reactionStep": {
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"reactionHash": "debe1ea0a0e9eca5f0acff94703ca321e00fa4061e1f2a231ee87c8aa59e3b21"
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"children": [
{
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"moleculeId": "sa_e11ca71068ddcf6649aafd11",
"parentId": "13174",
"isLeaf": true,
"molecule": {
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"inchikey": "DULSAGLWMRMKCQ-UHFFFAOYSA-N",
"smiles": "N#[C][Cu]"
},
"smiles": "N#[C][Cu]",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "13176",
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"moleculeId": "sa_02c65ea42854966276156cf7",
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"molecule": {
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"inchikey": "KHDDJQBUJMYKAY-UHFFFAOYSA-N",
"smiles": "OC1CCN(c2ncc(Br)cn2)CC1"
},
"smiles": "OC1CCN(c2ncc(Br)cn2)CC1",
"reactionStepId": "sa_c8a7129739afb27b04688e79",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090270434A1;0261;782109\",\"rsmi\":\"Cl[c:6]1[n:7][cH:8][c:9]([Br:10])[cH:11][n:12]1.[OH:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:13][CH2:14]1>CCN(CC)CC.CCO>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][c:9]([Br:10])[cH:11][n:12]2)[CH2:13][CH2:14]1\"},\"mapped_reaction_smiles\":\"Cl[c:6]1[n:7][cH:8][c:9]([Br:10])[cH:11][n:12]1.[OH:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:13][CH2:14]1>CCN(CC)CC.CCO>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][c:9]([Br:10])[cH:11][n:12]2)[CH2:13][CH2:14]1\"}",
"reactionStep": {
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"reactionHash": "8eccf4cc1fd338e03ee3cc3905de68f814cd3d00f8061aea78530843d2d67139"
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"children": [
{
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"moleculeId": "sa_49013ccb2f74ad800601ccf1",
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"molecule": {
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"inchikey": "HDOWRFHMPULYOA-UHFFFAOYSA-N",
"smiles": "OC1CCNCC1"
},
"smiles": "OC1CCNCC1",
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{
"id": "13178",
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"molecule": {
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"inchikey": "XPGIBDJXEVAVTO-UHFFFAOYSA-N",
"smiles": "Clc1ncc(Br)cn1"
},
"smiles": "Clc1ncc(Br)cn1",
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}
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]
},
{
"id": "13179",
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"molecule": {
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"inchikey": "PQJJJMRNHATNKG-UHFFFAOYSA-N",
"smiles": "CCOC(=O)CBr"
},
"smiles": "CCOC(=O)CBr",
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"children": []
}
]
}
]
}
]
}
}