Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CO[C@@]1(c2ccc(Cl)c(Cc3ccc(OCC(F)F)cc3)c2)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChiKey
PQJOOIIEOKIRNE-VOFPXKNKSA-N
Route Signature
6705066e46a81ccb800cf0a2f700879b4f93ab2a6c2447833f3883d3349782f4
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_f5b9022ac01128aecec32cd3",
"signature": "6705066e46a81ccb800cf0a2f700879b4f93ab2a6c2447833f3883d3349782f4",
"contentHash": "316007c3e771432df98eeb64a274afaf89bde2c23788824e0c6b77c79e76f82e",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_6720bd068374e4c4516efa75",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-01282",
"moleculeId": "sa_283554d811ba9d4333b07b9e",
"smiles": "CO[C@@]1(c2ccc(Cl)c(Cc3ccc(OCC(F)F)cc3)c2)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_283554d811ba9d4333b07b9e",
"inchikey": "PQJOOIIEOKIRNE-VOFPXKNKSA-N",
"smiles": "CO[C@@]1(c2ccc(Cl)c(Cc3ccc(OCC(F)F)cc3)c2)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "1455",
"routeId": "sa_f5b9022ac01128aecec32cd3",
"moleculeId": "sa_283554d811ba9d4333b07b9e",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_283554d811ba9d4333b07b9e",
"inchikey": "PQJOOIIEOKIRNE-VOFPXKNKSA-N",
"smiles": "CO[C@@]1(c2ccc(Cl)c(Cc3ccc(OCC(F)F)cc3)c2)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O"
},
"smiles": "CO[C@@]1(c2ccc(Cl)c(Cc3ccc(OCC(F)F)cc3)c2)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O",
"reactionStepId": "sa_e2981e5ded87cc5c6441e0fa",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130130997A1;0228;1371122\",\"rsmi\":\"Br[c:4]1[cH:5][c:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH2:13][CH:14]([F:15])[F:16])[cH:17][cH:18]2)[c:19]([Cl:20])[cH:21][cH:22]1.C[Si](C)(C)[O:26][CH2:25][C@H:24]1[O:23][C:3](=O)[C@H:31]([O:32][Si](C)(C)C)[C@@H:29]([O:30][Si](C)(C)C)[C@@H:27]1[O:28][Si](C)(C)C.[CH3:1][OH:2]>CCCCCC.COC(C)(C)C.CS(=O)(=O)O.O=C(O)O.[Li]CCCC.[Na+]>[CH3:1][O:2][C@@:3]1([c:4]2[cH:5][c:6]([CH2:7][c:8]3[cH:9][cH:10][c:11]([O:12][CH2:13][CH:14]([F:15])[F:16])[cH:17][cH:18]3)[c:19]([Cl:20])[cH:21][cH:22]2)[O:23][C@H:24]([CH2:25][OH:26])[C@@H:27]([OH:28])[C@H:29]([OH:30])[C@H:31]1[OH:32]\"},\"mapped_reaction_smiles\":\"Br[c:4]1[cH:5][c:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH2:13][CH:14]([F:15])[F:16])[cH:17][cH:18]2)[c:19]([Cl:20])[cH:21][cH:22]1.C[Si](C)(C)[O:26][CH2:25][C@H:24]1[O:23][C:3](=O)[C@H:31]([O:32][Si](C)(C)C)[C@@H:29]([O:30][Si](C)(C)C)[C@@H:27]1[O:28][Si](C)(C)C.[CH3:1][OH:2]>CCCCCC.COC(C)(C)C.CS(=O)(=O)O.O=C(O)O.[Li]CCCC.[Na+]>[CH3:1][O:2][C@@:3]1([c:4]2[cH:5][c:6]([CH2:7][c:8]3[cH:9][cH:10][c:11]([O:12][CH2:13][CH:14]([F:15])[F:16])[cH:17][cH:18]3)[c:19]([Cl:20])[cH:21][cH:22]2)[O:23][C@H:24]([CH2:25][OH:26])[C@@H:27]([OH:28])[C@H:29]([OH:30])[C@H:31]1[OH:32]\"}",
"reactionStep": {
"id": "sa_e2981e5ded87cc5c6441e0fa",
"reactionHash": "e65d9d5723002c0580c4c111269a3e96c8eaabef15b20bfe543a8a3291711a15"
},
"children": [
{
"id": "1456",
"routeId": "sa_f5b9022ac01128aecec32cd3",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "1455",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1457",
"routeId": "sa_f5b9022ac01128aecec32cd3",
"moleculeId": "sa_8e49c538e8b608b57a858ab1",
"parentId": "1455",
"isLeaf": false,
"molecule": {
"id": "sa_8e49c538e8b608b57a858ab1",
"inchikey": "RXWWLXYBRSNHSH-UHFFFAOYSA-N",
"smiles": "FC(F)COc1ccc(Cc2cc(Br)ccc2Cl)cc1"
},
"smiles": "FC(F)COc1ccc(Cc2cc(Br)ccc2Cl)cc1",
"reactionStepId": "sa_d795ba5afc1b5de170f64a27",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130130997A1;0227;1371121\",\"rsmi\":\"O=[C:10]([c:9]1[cH:8][cH:7][c:6]([O:5][CH2:4][CH:2]([F:1])[F:3])[cH:20][cH:19]1)[c:11]1[c:12]([Cl:13])[cH:14][cH:15][c:16]([Br:17])[cH:18]1>CC#N.CCOCC.CC[SiH](CC)CC.COC(C)(C)C.FB(F)F.O=C(O)O.[Na+]>[F:1][CH:2]([F:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][c:11]2[c:12]([Cl:13])[cH:14][cH:15][c:16]([Br:17])[cH:18]2)[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"O=[C:10]([c:9]1[cH:8][cH:7][c:6]([O:5][CH2:4][CH:2]([F:1])[F:3])[cH:20][cH:19]1)[c:11]1[c:12]([Cl:13])[cH:14][cH:15][c:16]([Br:17])[cH:18]1>CC#N.CCOCC.CC[SiH](CC)CC.COC(C)(C)C.FB(F)F.O=C(O)O.[Na+]>[F:1][CH:2]([F:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][c:11]2[c:12]([Cl:13])[cH:14][cH:15][c:16]([Br:17])[cH:18]2)[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_d795ba5afc1b5de170f64a27",
"reactionHash": "6b935a8814caf022be0b2f01ab29b88072f5d41f374c3a58f62dbb43f95ac106"
},
"children": [
{
"id": "1458",
"routeId": "sa_f5b9022ac01128aecec32cd3",
"moleculeId": "sa_6f0ec43d2f8e4d9aa8ef1a83",
"parentId": "1457",
"isLeaf": false,
"molecule": {
"id": "sa_6f0ec43d2f8e4d9aa8ef1a83",
"inchikey": "BRJOSBFTUMJFBU-UHFFFAOYSA-N",
"smiles": "O=C(c1ccc(OCC(F)F)cc1)c1cc(Br)ccc1Cl"
},
"smiles": "O=C(c1ccc(OCC(F)F)cc1)c1cc(Br)ccc1Cl",
"reactionStepId": "sa_a94db4c7064f6b3b127080a8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130130997A1;0226;1371120\",\"rsmi\":\"Cl[C:2](=[O:1])[c:14]1[c:15]([Cl:16])[cH:17][cH:18][c:19]([Br:20])[cH:21]1.[cH:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH:9]([F:10])[F:11])[cH:12][cH:13]1>ClCCl.[Al+3].Cl.Cl.Cl>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH:9]([F:10])[F:11])[cH:12][cH:13]1)[c:14]1[c:15]([Cl:16])[cH:17][cH:18][c:19]([Br:20])[cH:21]1\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[c:14]1[c:15]([Cl:16])[cH:17][cH:18][c:19]([Br:20])[cH:21]1.[cH:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH:9]([F:10])[F:11])[cH:12][cH:13]1>ClCCl.[Al+3].Cl.Cl.Cl>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH:9]([F:10])[F:11])[cH:12][cH:13]1)[c:14]1[c:15]([Cl:16])[cH:17][cH:18][c:19]([Br:20])[cH:21]1\"}",
"reactionStep": {
"id": "sa_a94db4c7064f6b3b127080a8",
"reactionHash": "7d6a032ea4365b8183a106a2e85d49042e1a5939409c722baeeba0f28764db28"
},
"children": [
{
"id": "1459",
"routeId": "sa_f5b9022ac01128aecec32cd3",
"moleculeId": "sa_08612a36640b96675711b4e0",
"parentId": "1458",
"isLeaf": false,
"molecule": {
"id": "sa_08612a36640b96675711b4e0",
"inchikey": "HOKWHGYUNYFNTP-UHFFFAOYSA-N",
"smiles": "FC(F)COc1ccccc1"
},
"smiles": "FC(F)COc1ccccc1",
"reactionStepId": "sa_d36535767be056763c9c1d4a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130130997A1;0224;1371118\",\"rsmi\":\"Br[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[F:1][CH:2]([F:3])[CH2:4][OH:5]>CN(C)C=O.[HH].[Na+]>[F:1][CH:2]([F:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1\"},\"mapped_reaction_smiles\":\"Br[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[F:1][CH:2]([F:3])[CH2:4][OH:5]>CN(C)C=O.[HH].[Na+]>[F:1][CH:2]([F:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1\"}",
"reactionStep": {
"id": "sa_d36535767be056763c9c1d4a",
"reactionHash": "6790e482027c1b4358f14080d0d4cca406f4bc20717f7ab49ab1203e6f0039ee"
},
"children": [
{
"id": "1460",
"routeId": "sa_f5b9022ac01128aecec32cd3",
"moleculeId": "sa_19352b1cfa6962c31e6d0462",
"parentId": "1459",
"isLeaf": true,
"molecule": {
"id": "sa_19352b1cfa6962c31e6d0462",
"inchikey": "QARVLSVVCXYDNA-UHFFFAOYSA-N",
"smiles": "Brc1ccccc1"
},
"smiles": "Brc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1461",
"routeId": "sa_f5b9022ac01128aecec32cd3",
"moleculeId": "sa_8c6fa32c5bb5876d9eb74e85",
"parentId": "1459",
"isLeaf": true,
"molecule": {
"id": "sa_8c6fa32c5bb5876d9eb74e85",
"inchikey": "VOGSDFLJZPNWHY-UHFFFAOYSA-N",
"smiles": "OCC(F)F"
},
"smiles": "OCC(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "1462",
"routeId": "sa_f5b9022ac01128aecec32cd3",
"moleculeId": "sa_efbfa7dc2dc8431eb3b45964",
"parentId": "1458",
"isLeaf": false,
"molecule": {
"id": "sa_efbfa7dc2dc8431eb3b45964",
"inchikey": "TZIQQJRRMJWMDI-UHFFFAOYSA-N",
"smiles": "O=C(Cl)c1cc(Br)ccc1Cl"
},
"smiles": "O=C(Cl)c1cc(Br)ccc1Cl",
"reactionStepId": "sa_4442018268c05481d7feaefd",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130130997A1;0225;1371119\",\"rsmi\":\"O=S(Cl)[Cl:3].O[C:2](=[O:1])[c:4]1[c:5]([Cl:6])[cH:7][cH:8][c:9]([Br:10])[cH:11]1>CN(C)C=O.Cc1ccccc1>[O:1]=[C:2]([Cl:3])[c:4]1[c:5]([Cl:6])[cH:7][cH:8][c:9]([Br:10])[cH:11]1\"},\"mapped_reaction_smiles\":\"O=S(Cl)[Cl:3].O[C:2](=[O:1])[c:4]1[c:5]([Cl:6])[cH:7][cH:8][c:9]([Br:10])[cH:11]1>CN(C)C=O.Cc1ccccc1>[O:1]=[C:2]([Cl:3])[c:4]1[c:5]([Cl:6])[cH:7][cH:8][c:9]([Br:10])[cH:11]1\"}",
"reactionStep": {
"id": "sa_4442018268c05481d7feaefd",
"reactionHash": "efdf73c541a5cc4f3f914e2e736f8621bc32b46984e9db665550602a3a2c3e53"
},
"children": [
{
"id": "1463",
"routeId": "sa_f5b9022ac01128aecec32cd3",
"moleculeId": "sa_2396440889cb56b725a52126",
"parentId": "1462",
"isLeaf": true,
"molecule": {
"id": "sa_2396440889cb56b725a52126",
"inchikey": "FGERXQWKKIVFQG-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cc(Br)ccc1Cl"
},
"smiles": "O=C(O)c1cc(Br)ccc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1464",
"routeId": "sa_f5b9022ac01128aecec32cd3",
"moleculeId": "sa_cd67ce42f230ef1a4063353c",
"parentId": "1462",
"isLeaf": true,
"molecule": {
"id": "sa_cd67ce42f230ef1a4063353c",
"inchikey": "FYSNRJHAOHDILO-UHFFFAOYSA-N",
"smiles": "O=S(Cl)Cl"
},
"smiles": "O=S(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "1465",
"routeId": "sa_f5b9022ac01128aecec32cd3",
"moleculeId": "sa_4d61a3a9defd9d44fa24551a",
"parentId": "1455",
"isLeaf": true,
"molecule": {
"id": "sa_4d61a3a9defd9d44fa24551a",
"inchikey": "VNGTZLYNGGLPIZ-WCXIOVBPSA-N",
"smiles": "C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C"
},
"smiles": "C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}