Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
FC(F)(F)c1ccccc1-c1cc(Cl)c2[nH]c(C3=NOC4(CCCCC4)C3)nc2c1
InChiKey
LAMDZOPKOOSIGM-UHFFFAOYSA-N
Route Signature
59b5b7ec20c32d9549bf58a8374fcbf72203b5e225394b4c3711666370340ca8
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_37562651d1d507a689b1f9ad",
"signature": "59b5b7ec20c32d9549bf58a8374fcbf72203b5e225394b4c3711666370340ca8",
"contentHash": "395009a4a0eafe31f423c8931967ea4f5f316172e02e174af8aa444d4c31e34b",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_6c02339ef060f37c72a5dfd7",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-03799",
"moleculeId": "sa_977a85a2b157f44e9e7c8466",
"smiles": "FC(F)(F)c1ccccc1-c1cc(Cl)c2[nH]c(C3=NOC4(CCCCC4)C3)nc2c1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_977a85a2b157f44e9e7c8466",
"inchikey": "LAMDZOPKOOSIGM-UHFFFAOYSA-N",
"smiles": "FC(F)(F)c1ccccc1-c1cc(Cl)c2[nH]c(C3=NOC4(CCCCC4)C3)nc2c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11063",
"routeId": "sa_37562651d1d507a689b1f9ad",
"moleculeId": "sa_977a85a2b157f44e9e7c8466",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_977a85a2b157f44e9e7c8466",
"inchikey": "LAMDZOPKOOSIGM-UHFFFAOYSA-N",
"smiles": "FC(F)(F)c1ccccc1-c1cc(Cl)c2[nH]c(C3=NOC4(CCCCC4)C3)nc2c1"
},
"smiles": "FC(F)(F)c1ccccc1-c1cc(Cl)c2[nH]c(C3=NOC4(CCCCC4)C3)nc2c1",
"reactionStepId": "sa_04945af1431bdd671c3cd6b1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08232409B2;0339;1214447\",\"rsmi\":\"O=[C:12](O)[C:13]1=[N:14][O:15][C:16]2([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:22]1.O=[N+:23]([O-])[c:9]1[cH:8][c:7](-[c:6]2[c:5]([C:2]([F:1])([F:3])[F:4])[cH:30][cH:29][cH:28][cH:27]2)[cH:26][c:24]([Cl:25])[c:10]1[NH2:11]>C1CCOC1.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl.[Fe].[HH].[Na+]>[F:1][C:2]([F:3])([F:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]3[c:10]([nH:11][c:12]([C:13]4=[N:14][O:15][C:16]5([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]5)[CH2:22]4)[n:23]3)[c:24]([Cl:25])[cH:26]2)[cH:27][cH:28][cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"O=[C:12](O)[C:13]1=[N:14][O:15][C:16]2([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:22]1.O=[N+:23]([O-])[c:9]1[cH:8][c:7](-[c:6]2[c:5]([C:2]([F:1])([F:3])[F:4])[cH:30][cH:29][cH:28][cH:27]2)[cH:26][c:24]([Cl:25])[c:10]1[NH2:11]>C1CCOC1.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl.[Fe].[HH].[Na+]>[F:1][C:2]([F:3])([F:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]3[c:10]([nH:11][c:12]([C:13]4=[N:14][O:15][C:16]5([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]5)[CH2:22]4)[n:23]3)[c:24]([Cl:25])[cH:26]2)[cH:27][cH:28][cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_04945af1431bdd671c3cd6b1",
"reactionHash": "ec0484111d2e8ee7b6599268c1858c9a9ef52c0691fd150108e565d6332fda16"
},
"children": [
{
"id": "11064",
"routeId": "sa_37562651d1d507a689b1f9ad",
"moleculeId": "sa_79bd34d9a17945555ff6f5a1",
"parentId": "11063",
"isLeaf": false,
"molecule": {
"id": "sa_79bd34d9a17945555ff6f5a1",
"inchikey": "FTWCGHJFEWJCMK-UHFFFAOYSA-N",
"smiles": "O=C(O)C1=NOC2(CCCCC2)C1"
},
"smiles": "O=C(O)C1=NOC2(CCCCC2)C1",
"reactionStepId": "sa_f59367106224b07dc0d6b87d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08232409B2;0289;1214434\",\"rsmi\":\"CC[O:3][C:2](=[O:1])[C:4]1=[N:5][O:6][C:7]2([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[CH2:13]1>CO.O.O.[Li+].O>[O:1]=[C:2]([OH:3])[C:4]1=[N:5][O:6][C:7]2([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[CH2:13]1\"},\"mapped_reaction_smiles\":\"CC[O:3][C:2](=[O:1])[C:4]1=[N:5][O:6][C:7]2([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[CH2:13]1>CO.O.O.[Li+].O>[O:1]=[C:2]([OH:3])[C:4]1=[N:5][O:6][C:7]2([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[CH2:13]1\"}",
"reactionStep": {
"id": "sa_f59367106224b07dc0d6b87d",
"reactionHash": "197e6f4ccd34cda2feef48e441f6592b6fe0f923d53b373a60f150fcb5ae28c3"
},
"children": [
{
"id": "11065",
"routeId": "sa_37562651d1d507a689b1f9ad",
"moleculeId": "sa_82e3054f29d1fc6dfcdb2408",
"parentId": "11064",
"isLeaf": true,
"molecule": {
"id": "sa_82e3054f29d1fc6dfcdb2408",
"inchikey": "KNTMLCGAAQJEQZ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1=NOC2(CCCCC2)C1"
},
"smiles": "CCOC(=O)C1=NOC2(CCCCC2)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "11066",
"routeId": "sa_37562651d1d507a689b1f9ad",
"moleculeId": "sa_160f887c64cb04a4c8b24a2d",
"parentId": "11063",
"isLeaf": false,
"molecule": {
"id": "sa_160f887c64cb04a4c8b24a2d",
"inchikey": "OVXLPBRRIKHJRL-UHFFFAOYSA-N",
"smiles": "Nc1c(Cl)cc(-c2ccccc2C(F)(F)F)cc1[N+](=O)[O-]"
},
"smiles": "Nc1c(Cl)cc(-c2ccccc2C(F)(F)F)cc1[N+](=O)[O-]",
"reactionStepId": "sa_a215a9427546ab73444b631d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08232409B2;0337;1214446\",\"rsmi\":\"O=C1CCC(=O)N1[Cl:4].[NH2:1][c:2]1[cH:3][cH:5][c:6](-[c:7]2[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][cH:15][cH:16]2)[cH:17][c:18]1[N+:19](=[O:20])[O-:21]>CC#N.CCOC(C)=O>[NH2:1][c:2]1[c:3]([Cl:4])[cH:5][c:6](-[c:7]2[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][cH:15][cH:16]2)[cH:17][c:18]1[N+:19](=[O:20])[O-:21]\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Cl:4].[NH2:1][c:2]1[cH:3][cH:5][c:6](-[c:7]2[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][cH:15][cH:16]2)[cH:17][c:18]1[N+:19](=[O:20])[O-:21]>CC#N.CCOC(C)=O>[NH2:1][c:2]1[c:3]([Cl:4])[cH:5][c:6](-[c:7]2[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][cH:15][cH:16]2)[cH:17][c:18]1[N+:19](=[O:20])[O-:21]\"}",
"reactionStep": {
"id": "sa_a215a9427546ab73444b631d",
"reactionHash": "a460a03a0ad9125c30e51df8481fc8fa24f05f5a4e7e233717a52ed177c60eba"
},
"children": [
{
"id": "11067",
"routeId": "sa_37562651d1d507a689b1f9ad",
"moleculeId": "sa_a576f9b9a2caa305053d217d",
"parentId": "11066",
"isLeaf": true,
"molecule": {
"id": "sa_a576f9b9a2caa305053d217d",
"inchikey": "JRNVZBWKYDBUCA-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Cl"
},
"smiles": "O=C1CCC(=O)N1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11068",
"routeId": "sa_37562651d1d507a689b1f9ad",
"moleculeId": "sa_8981ac11413f4e8ea40c831f",
"parentId": "11066",
"isLeaf": false,
"molecule": {
"id": "sa_8981ac11413f4e8ea40c831f",
"inchikey": "PPMPPBMAQNMACJ-UHFFFAOYSA-N",
"smiles": "Nc1ccc(-c2ccccc2C(F)(F)F)cc1[N+](=O)[O-]"
},
"smiles": "Nc1ccc(-c2ccccc2C(F)(F)F)cc1[N+](=O)[O-]",
"reactionStepId": "sa_46fa73bd19aacc624307ecb6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08232409B2;0335;1214445\",\"rsmi\":\"Br[c:8]1[cH:7][c:3]([N+:4](=[O:5])[O-:6])[c:2]([NH2:1])[cH:20][cH:19]1.OB(O)[c:9]1[c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16][cH:17][cH:18]1>ClCCl.Cl[Pd]Cl.[Fe+2]>[NH2:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8](-[c:9]2[c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"Br[c:8]1[cH:7][c:3]([N+:4](=[O:5])[O-:6])[c:2]([NH2:1])[cH:20][cH:19]1.OB(O)[c:9]1[c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16][cH:17][cH:18]1>ClCCl.Cl[Pd]Cl.[Fe+2]>[NH2:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8](-[c:9]2[c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_46fa73bd19aacc624307ecb6",
"reactionHash": "b7b44f022f7cab15e0d4b12417d9bf06b46a9140414e20f4844da1da8be696ad"
},
"children": [
{
"id": "11069",
"routeId": "sa_37562651d1d507a689b1f9ad",
"moleculeId": "sa_c3c58c718a37fa051462691c",
"parentId": "11068",
"isLeaf": true,
"molecule": {
"id": "sa_c3c58c718a37fa051462691c",
"inchikey": "JNSBEPKGFVENFS-UHFFFAOYSA-N",
"smiles": "OB(O)c1ccccc1C(F)(F)F"
},
"smiles": "OB(O)c1ccccc1C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11070",
"routeId": "sa_37562651d1d507a689b1f9ad",
"moleculeId": "sa_57d83c31a08350a326eac58f",
"parentId": "11068",
"isLeaf": true,
"molecule": {
"id": "sa_57d83c31a08350a326eac58f",
"inchikey": "ZCWBZRBJSPWUPG-UHFFFAOYSA-N",
"smiles": "Nc1ccc(Br)cc1[N+](=O)[O-]"
},
"smiles": "Nc1ccc(Br)cc1[N+](=O)[O-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}