Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cc(Nc2ncc(F)c3nn(-c4c(Cl)cc(N)cc4Cl)cc23)ncn1
InChiKey
BRPIOGZMALNFKA-UHFFFAOYSA-N
Route Signature
a16db6e32ffa18250fd4afe6ffaf595b1124c676dae54689de2c104df3fc5fb1
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_94efd5f24baaa865521e74c0",
"signature": "a16db6e32ffa18250fd4afe6ffaf595b1124c676dae54689de2c104df3fc5fb1",
"contentHash": "a43420923501f8cfb0f098b00d3fa6e44b82b9ae963022a755bd3b34457fbf45",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_a98ddb30e13e04aea0dd1f5e",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00228",
"moleculeId": "sa_b75f16a101c5539b3b280b17",
"smiles": "Cc1cc(Nc2ncc(F)c3nn(-c4c(Cl)cc(N)cc4Cl)cc23)ncn1",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_b75f16a101c5539b3b280b17",
"inchikey": "BRPIOGZMALNFKA-UHFFFAOYSA-N",
"smiles": "Cc1cc(Nc2ncc(F)c3nn(-c4c(Cl)cc(N)cc4Cl)cc23)ncn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12877",
"routeId": "sa_94efd5f24baaa865521e74c0",
"moleculeId": "sa_b75f16a101c5539b3b280b17",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_b75f16a101c5539b3b280b17",
"inchikey": "BRPIOGZMALNFKA-UHFFFAOYSA-N",
"smiles": "Cc1cc(Nc2ncc(F)c3nn(-c4c(Cl)cc(N)cc4Cl)cc23)ncn1"
},
"smiles": "Cc1cc(Nc2ncc(F)c3nn(-c4c(Cl)cc(N)cc4Cl)cc23)ncn1",
"reactionStepId": "sa_ce303f097b18b49ffd43d047",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09309240B2;1028;1748435\",\"rsmi\":\"O=[N+:19]([O-])[c:18]1[cH:17][c:15]([Cl:16])[c:14](-[n:13]2[n:12][c:11]3[c:9]([F:10])[cH:8][n:7][c:6]([NH:5][c:4]4[cH:3][c:2]([CH3:1])[n:27][cH:26][n:25]4)[c:24]3[cH:23]2)[c:21]([Cl:22])[cH:20]1>C1CCOC1.CCO.O.Cl.[Fe].N>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]3[n:12][n:13](-[c:14]4[c:15]([Cl:16])[cH:17][c:18]([NH2:19])[cH:20][c:21]4[Cl:22])[cH:23][c:24]23)[n:25][cH:26][n:27]1\"},\"mapped_reaction_smiles\":\"O=[N+:19]([O-])[c:18]1[cH:17][c:15]([Cl:16])[c:14](-[n:13]2[n:12][c:11]3[c:9]([F:10])[cH:8][n:7][c:6]([NH:5][c:4]4[cH:3][c:2]([CH3:1])[n:27][cH:26][n:25]4)[c:24]3[cH:23]2)[c:21]([Cl:22])[cH:20]1>C1CCOC1.CCO.O.Cl.[Fe].N>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]3[n:12][n:13](-[c:14]4[c:15]([Cl:16])[cH:17][c:18]([NH2:19])[cH:20][c:21]4[Cl:22])[cH:23][c:24]23)[n:25][cH:26][n:27]1\"}",
"reactionStep": {
"id": "sa_ce303f097b18b49ffd43d047",
"reactionHash": "be1f5963ce0d816f7277ef37436bb1147f6e79ef2fe67a7085584cc65a9778a3"
},
"children": [
{
"id": "12878",
"routeId": "sa_94efd5f24baaa865521e74c0",
"moleculeId": "sa_dbd1461fed2b5ec6ac1080c2",
"parentId": "12877",
"isLeaf": false,
"molecule": {
"id": "sa_dbd1461fed2b5ec6ac1080c2",
"inchikey": "SKUFSJZIULTYPH-UHFFFAOYSA-N",
"smiles": "Cc1cc(Nc2ncc(F)c3nn(-c4c(Cl)cc([N+](=O)[O-])cc4Cl)cc23)ncn1"
},
"smiles": "Cc1cc(Nc2ncc(F)c3nn(-c4c(Cl)cc([N+](=O)[O-])cc4Cl)cc23)ncn1",
"reactionStepId": "sa_e5135367b32cac5468063453",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09309240B2;1026;1748434\",\"rsmi\":\"Br[c:6]1[n:7][cH:8][c:9]([F:10])[c:11]2[n:12][n:13](-[c:14]3[c:15]([Cl:16])[cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:22][c:23]3[Cl:24])[cH:25][c:26]12.[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:27][cH:28][n:29]1>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd]>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]3[n:12][n:13](-[c:14]4[c:15]([Cl:16])[cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:22][c:23]4[Cl:24])[cH:25][c:26]23)[n:27][cH:28][n:29]1\"},\"mapped_reaction_smiles\":\"Br[c:6]1[n:7][cH:8][c:9]([F:10])[c:11]2[n:12][n:13](-[c:14]3[c:15]([Cl:16])[cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:22][c:23]3[Cl:24])[cH:25][c:26]12.[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:27][cH:28][n:29]1>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd]>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]3[n:12][n:13](-[c:14]4[c:15]([Cl:16])[cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:22][c:23]4[Cl:24])[cH:25][c:26]23)[n:27][cH:28][n:29]1\"}",
"reactionStep": {
"id": "sa_e5135367b32cac5468063453",
"reactionHash": "7630564c8f558ffc6a3cf4d29d12a596b98d952b918ff83679919a21446aba27"
},
"children": [
{
"id": "12879",
"routeId": "sa_94efd5f24baaa865521e74c0",
"moleculeId": "sa_59adf63174726c870619da3b",
"parentId": "12878",
"isLeaf": true,
"molecule": {
"id": "sa_59adf63174726c870619da3b",
"inchikey": "LAERIBHKDNBVOO-UHFFFAOYSA-N",
"smiles": "Cc1cc(N)ncn1"
},
"smiles": "Cc1cc(N)ncn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12880",
"routeId": "sa_94efd5f24baaa865521e74c0",
"moleculeId": "sa_89c37135e4636dd179dcf7b7",
"parentId": "12878",
"isLeaf": false,
"molecule": {
"id": "sa_89c37135e4636dd179dcf7b7",
"inchikey": "RUCPUJAUIVTQNH-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(Cl)c(-n2cc3c(Br)ncc(F)c3n2)c(Cl)c1"
},
"smiles": "O=[N+]([O-])c1cc(Cl)c(-n2cc3c(Br)ncc(F)c3n2)c(Cl)c1",
"reactionStepId": "sa_4f4d39987b97e26617f13e9a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09309240B2;1024;1748433\",\"rsmi\":\"C[Si](C)(C)[Br:13].Cl[c:12]1[c:11]2[cH:10][n:9](-[c:8]3[c:6]([Cl:7])[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:22][c:20]3[Cl:21])[n:19][c:18]2[c:16]([F:17])[cH:15][n:14]1>CCC#N>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[n:9]2[cH:10][c:11]3[c:12]([Br:13])[n:14][cH:15][c:16]([F:17])[c:18]3[n:19]2)[c:20]([Cl:21])[cH:22]1\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)[Br:13].Cl[c:12]1[c:11]2[cH:10][n:9](-[c:8]3[c:6]([Cl:7])[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:22][c:20]3[Cl:21])[n:19][c:18]2[c:16]([F:17])[cH:15][n:14]1>CCC#N>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[n:9]2[cH:10][c:11]3[c:12]([Br:13])[n:14][cH:15][c:16]([F:17])[c:18]3[n:19]2)[c:20]([Cl:21])[cH:22]1\"}",
"reactionStep": {
"id": "sa_4f4d39987b97e26617f13e9a",
"reactionHash": "c869c96df2c47e48ba07a11da6a89394e1ee858cd0c004ad1a8d3f5cc8800f97"
},
"children": [
{
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"routeId": "sa_94efd5f24baaa865521e74c0",
"moleculeId": "sa_916333c72507a75709c52d7e",
"parentId": "12880",
"isLeaf": false,
"molecule": {
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"inchikey": "IRUZMSWGCUBARD-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(Cl)c(-n2cc3c(Cl)ncc(F)c3n2)c(Cl)c1"
},
"smiles": "O=[N+]([O-])c1cc(Cl)c(-n2cc3c(Cl)ncc(F)c3n2)c(Cl)c1",
"reactionStepId": "sa_698c63ec751063885902000d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09309240B2;1022;1748432\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:13].[O-][n+:14]1[cH:12][c:11]2[cH:10][n:9](-[c:8]3[c:6]([Cl:7])[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:22][c:20]3[Cl:21])[n:19][c:18]2[c:16]([F:17])[cH:15]1>ClCCCl>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[n:9]2[cH:10][c:11]3[c:12]([Cl:13])[n:14][cH:15][c:16]([F:17])[c:18]3[n:19]2)[c:20]([Cl:21])[cH:22]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:13].[O-][n+:14]1[cH:12][c:11]2[cH:10][n:9](-[c:8]3[c:6]([Cl:7])[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:22][c:20]3[Cl:21])[n:19][c:18]2[c:16]([F:17])[cH:15]1>ClCCCl>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[n:9]2[cH:10][c:11]3[c:12]([Cl:13])[n:14][cH:15][c:16]([F:17])[c:18]3[n:19]2)[c:20]([Cl:21])[cH:22]1\"}",
"reactionStep": {
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{
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"molecule": {
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"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
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{
"id": "12883",
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"molecule": {
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"inchikey": "XZHIOLXVFLGVLP-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(Cl)c(-n2cc3c[n+]([O-])cc(F)c3n2)c(Cl)c1"
},
"smiles": "O=[N+]([O-])c1cc(Cl)c(-n2cc3c[n+]([O-])cc(F)c3n2)c(Cl)c1",
"reactionStepId": "sa_79093bd917543beebc8b3718",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09309240B2;1020;1748431\",\"rsmi\":\"O=C(O[OH:14])c1cccc(Cl)c1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[n:9]2[cH:10][c:11]3[cH:12][n:13][cH:15][c:16]([F:17])[c:18]3[n:19]2)[c:20]([Cl:21])[cH:22]1>ClCCl.O=S(=O)(O)O.[Na+].[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[n:9]2[cH:10][c:11]3[cH:12][n+:13]([O-:14])[cH:15][c:16]([F:17])[c:18]3[n:19]2)[c:20]([Cl:21])[cH:22]1\"},\"mapped_reaction_smiles\":\"O=C(O[OH:14])c1cccc(Cl)c1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[n:9]2[cH:10][c:11]3[cH:12][n:13][cH:15][c:16]([F:17])[c:18]3[n:19]2)[c:20]([Cl:21])[cH:22]1>ClCCl.O=S(=O)(O)O.[Na+].[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[n:9]2[cH:10][c:11]3[cH:12][n+:13]([O-:14])[cH:15][c:16]([F:17])[c:18]3[n:19]2)[c:20]([Cl:21])[cH:22]1\"}",
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"smiles": "O=[N+]([O-])c1cc(Cl)c(-n2cc3cncc(F)c3n2)c(Cl)c1"
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"smiles": "O=[N+]([O-])c1cc(Cl)c(-n2cc3cncc(F)c3n2)c(Cl)c1",
"reactionStepId": "sa_237026df686c5634d65e76e3",
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"metadata": "{\"annotations\":{\"ID\":\"US09309240B2;1018;1748430\",\"rsmi\":\"[N-]=[N+]=[N:18][c:17]1[c:11](/[CH:10]=[N:9]/[c:8]2[c:6]([Cl:7])[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:21][c:19]2[Cl:20])[cH:12][n:13][cH:14][c:15]1[F:16]>Cc1ccccc1>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[n:9]2[cH:10][c:11]3[cH:12][n:13][cH:14][c:15]([F:16])[c:17]3[n:18]2)[c:19]([Cl:20])[cH:21]1\"},\"mapped_reaction_smiles\":\"[N-]=[N+]=[N:18][c:17]1[c:11](/[CH:10]=[N:9]/[c:8]2[c:6]([Cl:7])[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:21][c:19]2[Cl:20])[cH:12][n:13][cH:14][c:15]1[F:16]>Cc1ccccc1>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[n:9]2[cH:10][c:11]3[cH:12][n:13][cH:14][c:15]([F:16])[c:17]3[n:18]2)[c:19]([Cl:20])[cH:21]1\"}",
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"metadata": "{\"annotations\":{\"ID\":\"US09309240B2;1016;1748429\",\"rsmi\":\"O=[CH:6][c:5]1[c:4]([N:3]=[N+:2]=[N-:1])[c:22]([F:23])[cH:21][n:20][cH:19]1.[NH2:7][c:8]1[c:9]([Cl:10])[cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]1[Cl:18]>CCN(CC)CC.ClCCl.Cl[Ti](Cl)(Cl)Cl>[N-:1]=[N+:2]=[N:3][c:4]1[c:5](/[CH:6]=[N:7]/[c:8]2[c:9]([Cl:10])[cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]2[Cl:18])[cH:19][n:20][cH:21][c:22]1[F:23]\"},\"mapped_reaction_smiles\":\"O=[CH:6][c:5]1[c:4]([N:3]=[N+:2]=[N-:1])[c:22]([F:23])[cH:21][n:20][cH:19]1.[NH2:7][c:8]1[c:9]([Cl:10])[cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]1[Cl:18]>CCN(CC)CC.ClCCl.Cl[Ti](Cl)(Cl)Cl>[N-:1]=[N+:2]=[N:3][c:4]1[c:5](/[CH:6]=[N:7]/[c:8]2[c:9]([Cl:10])[cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]2[Cl:18])[cH:19][n:20][cH:21][c:22]1[F:23]\"}",
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"molecule": {
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"smiles": "Nc1c(Cl)cc([N+](=O)[O-])cc1Cl"
},
"smiles": "Nc1c(Cl)cc([N+](=O)[O-])cc1Cl",
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},
{
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}