Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(Nc1cccc(-c2ccc3c(c2)CC(c2cc(Cl)cc(Cl)c2)(C(F)(F)F)O3)c1F)C1CC1
InChiKey
HYYYQPYCSFSCAX-UHFFFAOYSA-N
Route Signature
21cfbe4d6efa121157bc8e8cdf1075691d330550a6f1053bcba71ae24ce08abb
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_f48a399c76527dc4d2e0fb19",
"signature": "21cfbe4d6efa121157bc8e8cdf1075691d330550a6f1053bcba71ae24ce08abb",
"contentHash": "0a18d0388d83e3752433887f1310a2f2c7917fc99f179fe737860948e7bee992",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_e24442d1aee7197a2a411f0c",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00778",
"moleculeId": "sa_ed9676e6f7ef9a655ce951ed",
"smiles": "O=C(Nc1cccc(-c2ccc3c(c2)CC(c2cc(Cl)cc(Cl)c2)(C(F)(F)F)O3)c1F)C1CC1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_ed9676e6f7ef9a655ce951ed",
"inchikey": "HYYYQPYCSFSCAX-UHFFFAOYSA-N",
"smiles": "O=C(Nc1cccc(-c2ccc3c(c2)CC(c2cc(Cl)cc(Cl)c2)(C(F)(F)F)O3)c1F)C1CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9735",
"routeId": "sa_f48a399c76527dc4d2e0fb19",
"moleculeId": "sa_ed9676e6f7ef9a655ce951ed",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_ed9676e6f7ef9a655ce951ed",
"inchikey": "HYYYQPYCSFSCAX-UHFFFAOYSA-N",
"smiles": "O=C(Nc1cccc(-c2ccc3c(c2)CC(c2cc(Cl)cc(Cl)c2)(C(F)(F)F)O3)c1F)C1CC1"
},
"smiles": "O=C(Nc1cccc(-c2ccc3c(c2)CC(c2cc(Cl)cc(Cl)c2)(C(F)(F)F)O3)c1F)C1CC1",
"reactionStepId": "sa_7b51b79f83838f97f6780201",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016927A1;0809;1821534\",\"rsmi\":\"Cl[C:2](=[O:1])[CH:32]1[CH2:33][CH2:34]1.[NH2:3][c:4]1[c:5]([F:6])[c:7](-[c:8]2[cH:9][c:10]3[c:11]([cH:12][cH:13]2)[O:14][C:15]([c:16]2[cH:17][c:18]([Cl:19])[cH:20][c:21]([Cl:22])[cH:23]2)([C:24]([F:25])([F:26])[F:27])[CH2:28]3)[cH:29][cH:30][cH:31]1>C1CCOC1.CCN(CC)CC.O>[O:1]=[C:2]([NH:3][c:4]1[c:5]([F:6])[c:7](-[c:8]2[cH:9][c:10]3[c:11]([cH:12][cH:13]2)[O:14][C:15]([c:16]2[cH:17][c:18]([Cl:19])[cH:20][c:21]([Cl:22])[cH:23]2)([C:24]([F:25])([F:26])[F:27])[CH2:28]3)[cH:29][cH:30][cH:31]1)[CH:32]1[CH2:33][CH2:34]1\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[CH:32]1[CH2:33][CH2:34]1.[NH2:3][c:4]1[c:5]([F:6])[c:7](-[c:8]2[cH:9][c:10]3[c:11]([cH:12][cH:13]2)[O:14][C:15]([c:16]2[cH:17][c:18]([Cl:19])[cH:20][c:21]([Cl:22])[cH:23]2)([C:24]([F:25])([F:26])[F:27])[CH2:28]3)[cH:29][cH:30][cH:31]1>C1CCOC1.CCN(CC)CC.O>[O:1]=[C:2]([NH:3][c:4]1[c:5]([F:6])[c:7](-[c:8]2[cH:9][c:10]3[c:11]([cH:12][cH:13]2)[O:14][C:15]([c:16]2[cH:17][c:18]([Cl:19])[cH:20][c:21]([Cl:22])[cH:23]2)([C:24]([F:25])([F:26])[F:27])[CH2:28]3)[cH:29][cH:30][cH:31]1)[CH:32]1[CH2:33][CH2:34]1\"}",
"reactionStep": {
"id": "sa_7b51b79f83838f97f6780201",
"reactionHash": "5422f1a69bb53c538454f2d811a612903211e1080c0cbc345d2bd46c9e6a054d"
},
"children": [
{
"id": "9736",
"routeId": "sa_f48a399c76527dc4d2e0fb19",
"moleculeId": "sa_6715a82e937a534079a0bb75",
"parentId": "9735",
"isLeaf": false,
"molecule": {
"id": "sa_6715a82e937a534079a0bb75",
"inchikey": "NVOPIQCHNIYNDN-UHFFFAOYSA-N",
"smiles": "Nc1cccc(-c2ccc3c(c2)CC(c2cc(Cl)cc(Cl)c2)(C(F)(F)F)O3)c1F"
},
"smiles": "Nc1cccc(-c2ccc3c(c2)CC(c2cc(Cl)cc(Cl)c2)(C(F)(F)F)O3)c1F",
"reactionStepId": "sa_7bb0bab56c66e8f5e4668c7a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016927A1;0807;1821533\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[c:3]([F:4])[c:5](-[c:6]2[cH:7][c:8]3[c:9]([cH:10][cH:11]2)[O:12][C:13]([c:14]2[cH:15][c:16]([Cl:17])[cH:18][c:19]([Cl:20])[cH:21]2)([C:22]([F:23])([F:24])[F:25])[CH2:26]3)[cH:27][cH:28][cH:29]1>CO.O.[H][H].[Ni]>[NH2:1][c:2]1[c:3]([F:4])[c:5](-[c:6]2[cH:7][c:8]3[c:9]([cH:10][cH:11]2)[O:12][C:13]([c:14]2[cH:15][c:16]([Cl:17])[cH:18][c:19]([Cl:20])[cH:21]2)([C:22]([F:23])([F:24])[F:25])[CH2:26]3)[cH:27][cH:28][cH:29]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[c:3]([F:4])[c:5](-[c:6]2[cH:7][c:8]3[c:9]([cH:10][cH:11]2)[O:12][C:13]([c:14]2[cH:15][c:16]([Cl:17])[cH:18][c:19]([Cl:20])[cH:21]2)([C:22]([F:23])([F:24])[F:25])[CH2:26]3)[cH:27][cH:28][cH:29]1>CO.O.[H][H].[Ni]>[NH2:1][c:2]1[c:3]([F:4])[c:5](-[c:6]2[cH:7][c:8]3[c:9]([cH:10][cH:11]2)[O:12][C:13]([c:14]2[cH:15][c:16]([Cl:17])[cH:18][c:19]([Cl:20])[cH:21]2)([C:22]([F:23])([F:24])[F:25])[CH2:26]3)[cH:27][cH:28][cH:29]1\"}",
"reactionStep": {
"id": "sa_7bb0bab56c66e8f5e4668c7a",
"reactionHash": "94ed3fb38a5775acaa40cc911b5cda69f1c2e3fc5d7d94c364578d92def286f1"
},
"children": [
{
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"routeId": "sa_f48a399c76527dc4d2e0fb19",
"moleculeId": "sa_1503dd7e95c8f21fd48d265a",
"parentId": "9736",
"isLeaf": false,
"molecule": {
"id": "sa_1503dd7e95c8f21fd48d265a",
"inchikey": "MSJKWSUVYKCRTG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cccc(-c2ccc3c(c2)CC(c2cc(Cl)cc(Cl)c2)(C(F)(F)F)O3)c1F"
},
"smiles": "O=[N+]([O-])c1cccc(-c2ccc3c(c2)CC(c2cc(Cl)cc(Cl)c2)(C(F)(F)F)O3)c1F",
"reactionStepId": "sa_af2ecbfd914e269a3979098f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016927A1;0805;1821532\",\"rsmi\":\"CC1(C)OB([c:8]2[cH:7][cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:30]2[F:31])OC1(C)C.I[c:9]1[cH:10][c:11]2[c:12]([cH:13][cH:14]1)[O:15][C:16]([c:17]1[cH:18][c:19]([Cl:20])[cH:21][c:22]([Cl:23])[cH:24]1)([C:25]([F:26])([F:27])[F:28])[CH2:29]2>COCCOC.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[K+].[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[c:12]([cH:13][cH:14]2)[O:15][C:16]([c:17]2[cH:18][c:19]([Cl:20])[cH:21][c:22]([Cl:23])[cH:24]2)([C:25]([F:26])([F:27])[F:28])[CH2:29]3)[c:30]1[F:31]\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:8]2[cH:7][cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:30]2[F:31])OC1(C)C.I[c:9]1[cH:10][c:11]2[c:12]([cH:13][cH:14]1)[O:15][C:16]([c:17]1[cH:18][c:19]([Cl:20])[cH:21][c:22]([Cl:23])[cH:24]1)([C:25]([F:26])([F:27])[F:28])[CH2:29]2>COCCOC.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[K+].[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[c:12]([cH:13][cH:14]2)[O:15][C:16]([c:17]2[cH:18][c:19]([Cl:20])[cH:21][c:22]([Cl:23])[cH:24]2)([C:25]([F:26])([F:27])[F:28])[CH2:29]3)[c:30]1[F:31]\"}",
"reactionStep": {
"id": "sa_af2ecbfd914e269a3979098f",
"reactionHash": "c213b0914a47e59674257f921bc0b8f0ab0aed63f2e13c0823a270aeebc722f4"
},
"children": [
{
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"routeId": "sa_f48a399c76527dc4d2e0fb19",
"moleculeId": "sa_f8563fd0ec5e45a3a77afcae",
"parentId": "9737",
"isLeaf": false,
"molecule": {
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"inchikey": "MVXQKMGBOBJRAU-UHFFFAOYSA-N",
"smiles": "FC(F)(F)C1(c2cc(Cl)cc(Cl)c2)Cc2cc(I)ccc2O1"
},
"smiles": "FC(F)(F)C1(c2cc(Cl)cc(Cl)c2)Cc2cc(I)ccc2O1",
"reactionStepId": "sa_fabecaaa62b0867eecbfa25f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016927A1;0796;1821528\",\"rsmi\":\"N[c:19]1[cH:18][cH:17][c:16]2[c:15]([cH:21]1)[CH2:14][C:5]([C:2]([F:1])([F:3])[F:4])([c:6]1[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]1)[O:22]2.[IH:20]>O.O=NO.O=S(=O)(O)O.[K+].[Na+]>[F:1][C:2]([F:3])([F:4])[C:5]1([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]2)[CH2:14][c:15]2[c:16]([cH:17][cH:18][c:19]([I:20])[cH:21]2)[O:22]1\"},\"mapped_reaction_smiles\":\"N[c:19]1[cH:18][cH:17][c:16]2[c:15]([cH:21]1)[CH2:14][C:5]([C:2]([F:1])([F:3])[F:4])([c:6]1[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]1)[O:22]2.[IH:20]>O.O=NO.O=S(=O)(O)O.[K+].[Na+]>[F:1][C:2]([F:3])([F:4])[C:5]1([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]2)[CH2:14][c:15]2[c:16]([cH:17][cH:18][c:19]([I:20])[cH:21]2)[O:22]1\"}",
"reactionStep": {
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"reactionHash": "708c094b134900c93f2d9cb862eb80281d3141634626f79680c3288026fcc5ae"
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"children": [
{
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"routeId": "sa_f48a399c76527dc4d2e0fb19",
"moleculeId": "sa_a04005d32e319af10a70c4b7",
"parentId": "9738",
"isLeaf": false,
"molecule": {
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"inchikey": "LXJFOMLQHDUNHJ-UHFFFAOYSA-N",
"smiles": "Nc1ccc2c(c1)CC(c1cc(Cl)cc(Cl)c1)(C(F)(F)F)O2"
},
"smiles": "Nc1ccc2c(c1)CC(c1cc(Cl)cc(Cl)c1)(C(F)(F)F)O2",
"reactionStepId": "sa_f9fb0c2c7eb239ad94a2a30c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016927A1;0794;1821527\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[O:8][C:9]([c:10]1[cH:11][c:12]([Cl:13])[cH:14][c:15]([Cl:16])[cH:17]1)([C:18]([F:19])([F:20])[F:21])[CH2:22]2>C1CCOC1.CO.[H][H].[Ni]>[NH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[O:8][C:9]([c:10]1[cH:11][c:12]([Cl:13])[cH:14][c:15]([Cl:16])[cH:17]1)([C:18]([F:19])([F:20])[F:21])[CH2:22]2\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[O:8][C:9]([c:10]1[cH:11][c:12]([Cl:13])[cH:14][c:15]([Cl:16])[cH:17]1)([C:18]([F:19])([F:20])[F:21])[CH2:22]2>C1CCOC1.CO.[H][H].[Ni]>[NH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[O:8][C:9]([c:10]1[cH:11][c:12]([Cl:13])[cH:14][c:15]([Cl:16])[cH:17]1)([C:18]([F:19])([F:20])[F:21])[CH2:22]2\"}",
"reactionStep": {
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"children": [
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"moleculeId": "sa_53390154a3fcec031ec60eb8",
"parentId": "9739",
"isLeaf": true,
"molecule": {
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"inchikey": "NQDRSWBVFHJIPP-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc2c(c1)CC(c1cc(Cl)cc(Cl)c1)(C(F)(F)F)O2"
},
"smiles": "O=[N+]([O-])c1ccc2c(c1)CC(c1cc(Cl)cc(Cl)c1)(C(F)(F)F)O2",
"reactionStepId": null,
"template": null,
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}
]
},
{
"id": "9741",
"routeId": "sa_f48a399c76527dc4d2e0fb19",
"moleculeId": "sa_bc906e425e53d363266dfe60",
"parentId": "9738",
"isLeaf": true,
"molecule": {
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"inchikey": "XMBWDFGMSWQBCA-UHFFFAOYSA-N",
"smiles": "I"
},
"smiles": "I",
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}
]
},
{
"id": "9742",
"routeId": "sa_f48a399c76527dc4d2e0fb19",
"moleculeId": "sa_0422579e662b5f85d0217394",
"parentId": "9737",
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"molecule": {
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"inchikey": "RNRPIYYFOPOLSL-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cccc([N+](=O)[O-])c2F)OC1(C)C"
},
"smiles": "CC1(C)OB(c2cccc([N+](=O)[O-])c2F)OC1(C)C",
"reactionStepId": "sa_13152c74b6972c78a6a4e73f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016927A1;0803;1821531\",\"rsmi\":\"Br[c:6]1[c:7]([F:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][cH:15]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:17]([CH3:18])([CH3:19])[O:16]2)OC1(C)C>C1COCCO1.CC(=O)O.[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]([F:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][cH:15]2)[O:16][C:17]1([CH3:18])[CH3:19]\"},\"mapped_reaction_smiles\":\"Br[c:6]1[c:7]([F:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][cH:15]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:17]([CH3:18])([CH3:19])[O:16]2)OC1(C)C>C1COCCO1.CC(=O)O.[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]([F:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][cH:15]2)[O:16][C:17]1([CH3:18])[CH3:19]\"}",
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"children": [
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"molecule": {
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"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
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},
{
"id": "9744",
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"molecule": {
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"inchikey": "MWYFDHRLYOKUMH-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cccc(Br)c1F"
},
"smiles": "O=[N+]([O-])c1cccc(Br)c1F",
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}
]
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]
}
]
},
{
"id": "9745",
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"moleculeId": "sa_533af856f6df3abb2d70c000",
"parentId": "9735",
"isLeaf": true,
"molecule": {
"id": "sa_533af856f6df3abb2d70c000",
"inchikey": "ZOOSILUVXHVRJE-UHFFFAOYSA-N",
"smiles": "O=C(Cl)C1CC1"
},
"smiles": "O=C(Cl)C1CC1",
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}
]
}
}