Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cc(N2CCc3ncccc3C2)nc(N2CCCC2)c1NC(=O)Cc1cc(F)cc(F)c1
InChiKey
DGSWZMAIHOYLSZ-UHFFFAOYSA-N
Route Signature
84210cc8ca4d1c7e2de5e873d1bffcfa929b98047ecb60a68446cf5e88e6240d
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_53fb3f0d102a36d6a3bb279f",
"signature": "84210cc8ca4d1c7e2de5e873d1bffcfa929b98047ecb60a68446cf5e88e6240d",
"contentHash": "716ee4cc2878dea8629f5a667ae3c145a91426ae170f2c43324dcb03764ddaf3",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_2cf036ceb3a15c568f5e2c4f",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00823",
"moleculeId": "sa_f4b4499fb8fdceaf9250e806",
"smiles": "Cc1cc(N2CCc3ncccc3C2)nc(N2CCCC2)c1NC(=O)Cc1cc(F)cc(F)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_f4b4499fb8fdceaf9250e806",
"inchikey": "DGSWZMAIHOYLSZ-UHFFFAOYSA-N",
"smiles": "Cc1cc(N2CCc3ncccc3C2)nc(N2CCCC2)c1NC(=O)Cc1cc(F)cc(F)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "1186",
"routeId": "sa_53fb3f0d102a36d6a3bb279f",
"moleculeId": "sa_f4b4499fb8fdceaf9250e806",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f4b4499fb8fdceaf9250e806",
"inchikey": "DGSWZMAIHOYLSZ-UHFFFAOYSA-N",
"smiles": "Cc1cc(N2CCc3ncccc3C2)nc(N2CCCC2)c1NC(=O)Cc1cc(F)cc(F)c1"
},
"smiles": "Cc1cc(N2CCc3ncccc3C2)nc(N2CCCC2)c1NC(=O)Cc1cc(F)cc(F)c1",
"reactionStepId": "sa_bfb5d6adec837e0df1fb65aa",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120115900A1;0199;1212064\",\"rsmi\":\"Cl[C:5](=[O:6])[CH2:7][c:8]1[cH:9][c:10]([F:11])[cH:12][c:13]([F:14])[cH:15]1.O=[N+:4]([O-])[c:3]1[c:2]([CH3:1])[cH:34][c:23]([N:24]2[CH2:25][CH2:26][c:27]3[c:28]([cH:29][cH:30][cH:31][n:32]3)[CH2:33]2)[n:22][c:16]1[N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1>C1CCOC1.NN.O.[Ni]>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][c:8]2[cH:9][c:10]([F:11])[cH:12][c:13]([F:14])[cH:15]2)[c:16]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[n:22][c:23]([N:24]2[CH2:25][CH2:26][c:27]3[c:28]([cH:29][cH:30][cH:31][n:32]3)[CH2:33]2)[cH:34]1\"},\"mapped_reaction_smiles\":\"Cl[C:5](=[O:6])[CH2:7][c:8]1[cH:9][c:10]([F:11])[cH:12][c:13]([F:14])[cH:15]1.O=[N+:4]([O-])[c:3]1[c:2]([CH3:1])[cH:34][c:23]([N:24]2[CH2:25][CH2:26][c:27]3[c:28]([cH:29][cH:30][cH:31][n:32]3)[CH2:33]2)[n:22][c:16]1[N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1>C1CCOC1.NN.O.[Ni]>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][c:8]2[cH:9][c:10]([F:11])[cH:12][c:13]([F:14])[cH:15]2)[c:16]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[n:22][c:23]([N:24]2[CH2:25][CH2:26][c:27]3[c:28]([cH:29][cH:30][cH:31][n:32]3)[CH2:33]2)[cH:34]1\"}",
"reactionStep": {
"id": "sa_bfb5d6adec837e0df1fb65aa",
"reactionHash": "e3a7dfec406ff06c71ae97126d4562099f0ca4ce9c1fa59f1716056c58e628ac"
},
"children": [
{
"id": "1187",
"routeId": "sa_53fb3f0d102a36d6a3bb279f",
"moleculeId": "sa_a5bf777b78a8ebebd0ff3c5f",
"parentId": "1186",
"isLeaf": false,
"molecule": {
"id": "sa_a5bf777b78a8ebebd0ff3c5f",
"inchikey": "BXGRRPFIJUHRSM-UHFFFAOYSA-N",
"smiles": "Cc1cc(N2CCc3ncccc3C2)nc(N2CCCC2)c1[N+](=O)[O-]"
},
"smiles": "Cc1cc(N2CCc3ncccc3C2)nc(N2CCCC2)c1[N+](=O)[O-]",
"reactionStepId": "sa_8d4d77af2ac62b7ac666d817",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120115900A1;0191;1212060\",\"rsmi\":\"Cl[c:4]1[cH:3][c:2]([CH3:1])[c:22]([N+:23](=[O:24])[O-:25])[c:16]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[n:15]1.[NH:5]1[CH2:6][CH2:7][c:8]2[c:9]([cH:10][cH:11][cH:12][n:13]2)[CH2:14]1>CS(C)=O.O>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][c:8]3[c:9]([cH:10][cH:11][cH:12][n:13]3)[CH2:14]2)[n:15][c:16]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[c:22]1[N+:23](=[O:24])[O-:25]\"},\"mapped_reaction_smiles\":\"Cl[c:4]1[cH:3][c:2]([CH3:1])[c:22]([N+:23](=[O:24])[O-:25])[c:16]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[n:15]1.[NH:5]1[CH2:6][CH2:7][c:8]2[c:9]([cH:10][cH:11][cH:12][n:13]2)[CH2:14]1>CS(C)=O.O>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][c:8]3[c:9]([cH:10][cH:11][cH:12][n:13]3)[CH2:14]2)[n:15][c:16]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[c:22]1[N+:23](=[O:24])[O-:25]\"}",
"reactionStep": {
"id": "sa_8d4d77af2ac62b7ac666d817",
"reactionHash": "09c0749d481f8609a880951e889e7e70c1dd4b977a85e46a59c2b1adc488a7fb"
},
"children": [
{
"id": "1188",
"routeId": "sa_53fb3f0d102a36d6a3bb279f",
"moleculeId": "sa_1c4ac2bb8210cc2f7f083070",
"parentId": "1187",
"isLeaf": true,
"molecule": {
"id": "sa_1c4ac2bb8210cc2f7f083070",
"inchikey": "FPEAARFNXIWCTP-UHFFFAOYSA-N",
"smiles": "c1cnc2c(c1)CNCC2"
},
"smiles": "c1cnc2c(c1)CNCC2",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1189",
"routeId": "sa_53fb3f0d102a36d6a3bb279f",
"moleculeId": "sa_ce30f68c4693c88ab35cf571",
"parentId": "1187",
"isLeaf": false,
"molecule": {
"id": "sa_ce30f68c4693c88ab35cf571",
"inchikey": "MROHSPXAAHOXFO-UHFFFAOYSA-N",
"smiles": "Cc1cc(Cl)nc(N2CCCC2)c1[N+](=O)[O-]"
},
"smiles": "Cc1cc(Cl)nc(N2CCCC2)c1[N+](=O)[O-]",
"reactionStepId": "sa_11bae5c9825a393f3271e421",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120115900A1;0185;1212057\",\"rsmi\":\"Cl[c:7]1[c:3]([N+:4](=[O:5])[O-:6])[c:2]([CH3:1])[cH:16][c:14]([Cl:15])[n:13]1.[NH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1>CC#N.O>[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[c:7]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)[n:13][c:14]([Cl:15])[cH:16]1\"},\"mapped_reaction_smiles\":\"Cl[c:7]1[c:3]([N+:4](=[O:5])[O-:6])[c:2]([CH3:1])[cH:16][c:14]([Cl:15])[n:13]1.[NH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1>CC#N.O>[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[c:7]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)[n:13][c:14]([Cl:15])[cH:16]1\"}",
"reactionStep": {
"id": "sa_11bae5c9825a393f3271e421",
"reactionHash": "70e728401e32efca17b2792110389d6dc6f4c6853a12d57d200760817a4b8c56"
},
"children": [
{
"id": "1190",
"routeId": "sa_53fb3f0d102a36d6a3bb279f",
"moleculeId": "sa_943c8297af055ccb991dd258",
"parentId": "1189",
"isLeaf": false,
"molecule": {
"id": "sa_943c8297af055ccb991dd258",
"inchikey": "CMJNIYUZFQWYCK-UHFFFAOYSA-N",
"smiles": "Cc1cc(Cl)nc(Cl)c1[N+](=O)[O-]"
},
"smiles": "Cc1cc(Cl)nc(Cl)c1[N+](=O)[O-]",
"reactionStepId": "sa_c64ce2992e6a8c51a360c920",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120115900A1;0183;1212056\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:8].[O-][n+:9]1[cH:7][c:3]([N+:4](=[O:5])[O-:6])[c:2]([CH3:1])[cH:12][c:10]1[Cl:11]>>[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[c:7]([Cl:8])[n:9][c:10]([Cl:11])[cH:12]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:8].[O-][n+:9]1[cH:7][c:3]([N+:4](=[O:5])[O-:6])[c:2]([CH3:1])[cH:12][c:10]1[Cl:11]>>[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[c:7]([Cl:8])[n:9][c:10]([Cl:11])[cH:12]1\"}",
"reactionStep": {
"id": "sa_c64ce2992e6a8c51a360c920",
"reactionHash": "ea70479413a5e2063847381b4ab05bb1ee8b361ccea3e3cdb96bbebac9b291a2"
},
"children": [
{
"id": "1191",
"routeId": "sa_53fb3f0d102a36d6a3bb279f",
"moleculeId": "sa_8de902e4b5d3c7a5cfbe8f70",
"parentId": "1190",
"isLeaf": false,
"molecule": {
"id": "sa_8de902e4b5d3c7a5cfbe8f70",
"inchikey": "UPOSBORDHOMNNA-UHFFFAOYSA-N",
"smiles": "Cc1cc(Cl)[n+]([O-])cc1[N+](=O)[O-]"
},
"smiles": "Cc1cc(Cl)[n+]([O-])cc1[N+](=O)[O-]",
"reactionStepId": "sa_2891fe959bc6f0c56912977f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120115900A1;0181;1212055\",\"rsmi\":\"O[OH:7].[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[n:6][cH:8][c:9]1[N+:10](=[O:11])[O-:12]>ClCCl.NC(N)=O.O.O=C(OC(=O)C(F)(F)F)C(F)(F)F>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[n+:6]([O-:7])[cH:8][c:9]1[N+:10](=[O:11])[O-:12]\"},\"mapped_reaction_smiles\":\"O[OH:7].[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[n:6][cH:8][c:9]1[N+:10](=[O:11])[O-:12]>ClCCl.NC(N)=O.O.O=C(OC(=O)C(F)(F)F)C(F)(F)F>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[n+:6]([O-:7])[cH:8][c:9]1[N+:10](=[O:11])[O-:12]\"}",
"reactionStep": {
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"reactionHash": "e37e8e51e835eb7a43c796c64978469dbafac8ccd932ec3f2f8150cd0f1426ae"
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"children": [
{
"id": "1192",
"routeId": "sa_53fb3f0d102a36d6a3bb279f",
"moleculeId": "sa_ff1546b53b22da1d072c7c94",
"parentId": "1191",
"isLeaf": true,
"molecule": {
"id": "sa_ff1546b53b22da1d072c7c94",
"inchikey": "HWZUMEVIIGNXGM-UHFFFAOYSA-N",
"smiles": "Cc1cc(Cl)ncc1[N+](=O)[O-]"
},
"smiles": "Cc1cc(Cl)ncc1[N+](=O)[O-]",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "1193",
"routeId": "sa_53fb3f0d102a36d6a3bb279f",
"moleculeId": "sa_4dba68d938224067da688ab5",
"parentId": "1191",
"isLeaf": true,
"molecule": {
"id": "sa_4dba68d938224067da688ab5",
"inchikey": "MHAJPDPJQMAIIY-UHFFFAOYSA-N",
"smiles": "OO"
},
"smiles": "OO",
"reactionStepId": null,
"template": null,
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}
]
},
{
"id": "1194",
"routeId": "sa_53fb3f0d102a36d6a3bb279f",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "1190",
"isLeaf": true,
"molecule": {
"id": "sa_312a7cd3d48a055e9bc98180",
"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
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}
]
},
{
"id": "1195",
"routeId": "sa_53fb3f0d102a36d6a3bb279f",
"moleculeId": "sa_62377f86fd21f04e8ff496ef",
"parentId": "1189",
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"molecule": {
"id": "sa_62377f86fd21f04e8ff496ef",
"inchikey": "RWRDLPDLKQPQOW-UHFFFAOYSA-N",
"smiles": "C1CCNC1"
},
"smiles": "C1CCNC1",
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}
]
}
]
},
{
"id": "1196",
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"moleculeId": "sa_c5dcef594fedb99f100a42a5",
"parentId": "1186",
"isLeaf": false,
"molecule": {
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"inchikey": "WMVPARKLYWQLNN-UHFFFAOYSA-N",
"smiles": "O=C(Cl)Cc1cc(F)cc(F)c1"
},
"smiles": "O=C(Cl)Cc1cc(F)cc(F)c1",
"reactionStepId": "sa_d195a7285f6d2411d81f55f9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120115900A1;0197;1212063\",\"rsmi\":\"O=C(Cl)C(=O)[Cl:3].O[C:2](=[O:1])[CH2:4][c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]1>CN(C)C=O.ClCCl>[O:1]=[C:2]([Cl:3])[CH2:4][c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]1\"},\"mapped_reaction_smiles\":\"O=C(Cl)C(=O)[Cl:3].O[C:2](=[O:1])[CH2:4][c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]1>CN(C)C=O.ClCCl>[O:1]=[C:2]([Cl:3])[CH2:4][c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]1\"}",
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"children": [
{
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"molecule": {
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"smiles": "O=C(Cl)C(=O)Cl"
},
"smiles": "O=C(Cl)C(=O)Cl",
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{
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"molecule": {
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},
"smiles": "O=C(O)Cc1cc(F)cc(F)c1",
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}
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]
}
}