Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)(C)OC(=O)NCC1Oc2c(Cl)cc(Br)cc2C1O
InChiKey
IKXIOJXADQWNBY-UHFFFAOYSA-N
Route Signature
358a5c2d5140141a384b3bb456da660ad9f957ec1c3545367817e40d258895aa
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_d9fd5aaae2257fa84bbaa175",
"signature": "358a5c2d5140141a384b3bb456da660ad9f957ec1c3545367817e40d258895aa",
"contentHash": "8fdb82c9ee27ae1173bbb930082d07bf36231d89fc50a4af4fe952838b5e2610",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_e2990633cbd6bcf127f2e7e5",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00098",
"moleculeId": "sa_092379836bab58f58adfdf80",
"smiles": "CC(C)(C)OC(=O)NCC1Oc2c(Cl)cc(Br)cc2C1O",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_092379836bab58f58adfdf80",
"inchikey": "IKXIOJXADQWNBY-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NCC1Oc2c(Cl)cc(Br)cc2C1O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12411",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_092379836bab58f58adfdf80",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_092379836bab58f58adfdf80",
"inchikey": "IKXIOJXADQWNBY-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NCC1Oc2c(Cl)cc(Br)cc2C1O"
},
"smiles": "CC(C)(C)OC(=O)NCC1Oc2c(Cl)cc(Br)cc2C1O",
"reactionStepId": "sa_2c189b32423d7111a0c75ebd",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160221994A1;1081;1914720\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH2:8][CH2:9][CH:10]1[O:11][c:12]2[c:13]([cH:14][c:15]([Br:16])[cH:17][c:18]2[Cl:19])[CH:20]1[OH:21]>CCN(CC)CC.ClCCl.O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]1[O:11][c:12]2[c:13]([cH:14][c:15]([Br:16])[cH:17][c:18]2[Cl:19])[CH:20]1[OH:21]\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH2:8][CH2:9][CH:10]1[O:11][c:12]2[c:13]([cH:14][c:15]([Br:16])[cH:17][c:18]2[Cl:19])[CH:20]1[OH:21]>CCN(CC)CC.ClCCl.O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]1[O:11][c:12]2[c:13]([cH:14][c:15]([Br:16])[cH:17][c:18]2[Cl:19])[CH:20]1[OH:21]\"}",
"reactionStep": {
"id": "sa_2c189b32423d7111a0c75ebd",
"reactionHash": "dd6ab166371ff001799e57c7aa8c2961d232be2c8c4a81a0dca10e0f7f762224"
},
"children": [
{
"id": "12412",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_b273d4d4546165bca2b249b5",
"parentId": "12411",
"isLeaf": true,
"molecule": {
"id": "sa_b273d4d4546165bca2b249b5",
"inchikey": "DYHSDKLCOJIUFX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C"
},
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12413",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_a466a50fb1e075727e3af94b",
"parentId": "12411",
"isLeaf": false,
"molecule": {
"id": "sa_a466a50fb1e075727e3af94b",
"inchikey": "TVSCNNQYEXJBIT-UHFFFAOYSA-N",
"smiles": "NCC1Oc2c(Cl)cc(Br)cc2C1O"
},
"smiles": "NCC1Oc2c(Cl)cc(Br)cc2C1O",
"reactionStepId": "sa_7ddd6c8a4dbc3ee9b66972d0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160221994A1;1080;1914719\",\"rsmi\":\"[N-]=[N+]=[N:1][CH2:2][CH:3]1[O:4][c:5]2[c:6]([cH:7][c:8]([Br:9])[cH:10][c:11]2[Cl:12])[CH:13]1[OH:14]>CO.[Ni]>[NH2:1][CH2:2][CH:3]1[O:4][c:5]2[c:6]([cH:7][c:8]([Br:9])[cH:10][c:11]2[Cl:12])[CH:13]1[OH:14]\"},\"mapped_reaction_smiles\":\"[N-]=[N+]=[N:1][CH2:2][CH:3]1[O:4][c:5]2[c:6]([cH:7][c:8]([Br:9])[cH:10][c:11]2[Cl:12])[CH:13]1[OH:14]>CO.[Ni]>[NH2:1][CH2:2][CH:3]1[O:4][c:5]2[c:6]([cH:7][c:8]([Br:9])[cH:10][c:11]2[Cl:12])[CH:13]1[OH:14]\"}",
"reactionStep": {
"id": "sa_7ddd6c8a4dbc3ee9b66972d0",
"reactionHash": "1dc6d5f4f4867c4c3ef41cbbbe033a5d174e0509642a52c48a400d9324b9dfe1"
},
"children": [
{
"id": "12414",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_0c47b54167d36751a45cf4fb",
"parentId": "12413",
"isLeaf": false,
"molecule": {
"id": "sa_0c47b54167d36751a45cf4fb",
"inchikey": "RROTVRRTGJGRIL-UHFFFAOYSA-N",
"smiles": "[N-]=[N+]=NCC1Oc2c(Cl)cc(Br)cc2C1O"
},
"smiles": "[N-]=[N+]=NCC1Oc2c(Cl)cc(Br)cc2C1O",
"reactionStepId": "sa_1cfb7124a744933bd0a57799",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160221994A1;1079;1914718\",\"rsmi\":\"CS(=O)(=O)O[CH2:4][CH:5]1[O:6][c:7]2[c:8]([cH:9][c:10]([Br:11])[cH:12][c:13]2[Cl:14])[CH:15]1[OH:16].[N-:1]=[N+:2]=[N-:3]>CN(C)C=O.O.O=C(O)O.[K+].[K+].[Na+]>[N-:1]=[N+:2]=[N:3][CH2:4][CH:5]1[O:6][c:7]2[c:8]([cH:9][c:10]([Br:11])[cH:12][c:13]2[Cl:14])[CH:15]1[OH:16]\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[CH2:4][CH:5]1[O:6][c:7]2[c:8]([cH:9][c:10]([Br:11])[cH:12][c:13]2[Cl:14])[CH:15]1[OH:16].[N-:1]=[N+:2]=[N-:3]>CN(C)C=O.O.O=C(O)O.[K+].[K+].[Na+]>[N-:1]=[N+:2]=[N:3][CH2:4][CH:5]1[O:6][c:7]2[c:8]([cH:9][c:10]([Br:11])[cH:12][c:13]2[Cl:14])[CH:15]1[OH:16]\"}",
"reactionStep": {
"id": "sa_1cfb7124a744933bd0a57799",
"reactionHash": "8171ca0dfd36b9b7e9115b2f7f86795201c9c6bdebec62f354d37c11872c1fcf"
},
"children": [
{
"id": "12415",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_150dcc1bb50a379ead66b940",
"parentId": "12414",
"isLeaf": false,
"molecule": {
"id": "sa_150dcc1bb50a379ead66b940",
"inchikey": "IPRCGCVWNWMVIR-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)OCC1Oc2c(Cl)cc(Br)cc2C1O"
},
"smiles": "CS(=O)(=O)OCC1Oc2c(Cl)cc(Br)cc2C1O",
"reactionStepId": "sa_3e4d6860bfd18ad5cdd1c0fa",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160221994A1;1078;1914717\",\"rsmi\":\"Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH:7]1[O:8][c:9]2[c:10]([cH:11][c:12]([Br:13])[cH:14][c:15]2[Cl:16])[CH:17]1[OH:18]>CCN(CC)CC.ClCCl.O>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH:7]1[O:8][c:9]2[c:10]([cH:11][c:12]([Br:13])[cH:14][c:15]2[Cl:16])[CH:17]1[OH:18]\"},\"mapped_reaction_smiles\":\"Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH:7]1[O:8][c:9]2[c:10]([cH:11][c:12]([Br:13])[cH:14][c:15]2[Cl:16])[CH:17]1[OH:18]>CCN(CC)CC.ClCCl.O>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH:7]1[O:8][c:9]2[c:10]([cH:11][c:12]([Br:13])[cH:14][c:15]2[Cl:16])[CH:17]1[OH:18]\"}",
"reactionStep": {
"id": "sa_3e4d6860bfd18ad5cdd1c0fa",
"reactionHash": "dbdd1de18c3590eaa525ce1ab7634731336939af2c4f4da2f2c4b0dbdb8584c2"
},
"children": [
{
"id": "12416",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_29954d918c9beb2441837db0",
"parentId": "12415",
"isLeaf": false,
"molecule": {
"id": "sa_29954d918c9beb2441837db0",
"inchikey": "NFYJLDAZQJIYOZ-UHFFFAOYSA-N",
"smiles": "OCC1Oc2c(Cl)cc(Br)cc2C1O"
},
"smiles": "OCC1Oc2c(Cl)cc(Br)cc2C1O",
"reactionStepId": "sa_4b78fef37ca9d3a775777100",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160221994A1;1077;1914716\",\"rsmi\":\"O=C(O[OH:1])c1cccc(Cl)c1.[CH2:2]=[CH:3][CH:13]([c:6]1[c:5]([OH:4])[c:11]([Cl:12])[cH:10][c:8]([Br:9])[cH:7]1)[OH:14]>ClCCl.O.[K+].O>[OH:1][CH2:2][CH:3]1[O:4][c:5]2[c:6]([cH:7][c:8]([Br:9])[cH:10][c:11]2[Cl:12])[CH:13]1[OH:14]\"},\"mapped_reaction_smiles\":\"O=C(O[OH:1])c1cccc(Cl)c1.[CH2:2]=[CH:3][CH:13]([c:6]1[c:5]([OH:4])[c:11]([Cl:12])[cH:10][c:8]([Br:9])[cH:7]1)[OH:14]>ClCCl.O.[K+].O>[OH:1][CH2:2][CH:3]1[O:4][c:5]2[c:6]([cH:7][c:8]([Br:9])[cH:10][c:11]2[Cl:12])[CH:13]1[OH:14]\"}",
"reactionStep": {
"id": "sa_4b78fef37ca9d3a775777100",
"reactionHash": "73dcbd95c404ef0528a64d8f0e2590b87555e6f8516c352dd731c0186b4ecc15"
},
"children": [
{
"id": "12417",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_292aab804b3670e84ce954f3",
"parentId": "12416",
"isLeaf": true,
"molecule": {
"id": "sa_292aab804b3670e84ce954f3",
"inchikey": "NHQDETIJWKXCTC-UHFFFAOYSA-N",
"smiles": "O=C(OO)c1cccc(Cl)c1"
},
"smiles": "O=C(OO)c1cccc(Cl)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12418",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_a8f00b3c6ca675396d5809c4",
"parentId": "12416",
"isLeaf": false,
"molecule": {
"id": "sa_a8f00b3c6ca675396d5809c4",
"inchikey": "PNJHHUILNLGIAV-UHFFFAOYSA-N",
"smiles": "C=CC(O)c1cc(Br)cc(Cl)c1O"
},
"smiles": "C=CC(O)c1cc(Br)cc(Cl)c1O",
"reactionStepId": "sa_54453315aef34a3864f363ff",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160221994A1;1076;1914715\",\"rsmi\":\"Br[Mg][CH:2]=[CH2:1].[CH:3](=[O:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([Cl:11])[c:12]1[OH:13]>>[CH2:1]=[CH:2][CH:3]([OH:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([Cl:11])[c:12]1[OH:13]\"},\"mapped_reaction_smiles\":\"Br[Mg][CH:2]=[CH2:1].[CH:3](=[O:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([Cl:11])[c:12]1[OH:13]>>[CH2:1]=[CH:2][CH:3]([OH:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([Cl:11])[c:12]1[OH:13]\"}",
"reactionStep": {
"id": "sa_54453315aef34a3864f363ff",
"reactionHash": "09bbea6e48e3654397575ffe5b48963b417c4c3a26446f0f2fe0a57ded7b94ad"
},
"children": [
{
"id": "12419",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_8cf6808f0629b06d62310d0a",
"parentId": "12418",
"isLeaf": true,
"molecule": {
"id": "sa_8cf6808f0629b06d62310d0a",
"inchikey": "XHHHAXOHMKAOSL-UHFFFAOYSA-M",
"smiles": "C=[CH][Mg][Br]"
},
"smiles": "C=[CH][Mg][Br]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12420",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_363ec3130b93f95ff2b3df93",
"parentId": "12418",
"isLeaf": false,
"molecule": {
"id": "sa_363ec3130b93f95ff2b3df93",
"inchikey": "XXFFEGBFFXHMTF-UHFFFAOYSA-N",
"smiles": "O=Cc1cc(Br)cc(Cl)c1O"
},
"smiles": "O=Cc1cc(Br)cc(Cl)c1O",
"reactionStepId": "sa_805f05fbf76e092166b0ed6d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160221994A1;1075;1914714\",\"rsmi\":\"C1N2CN3CN1CN(C2)[CH2:2]3.[OH2:1].[cH:3]1[c:4]([OH:5])[c:6]([Cl:7])[cH:8][c:9]([Br:10])[cH:11]1>O=C(O)C(F)(F)F.O=S(=O)(O)O>[O:1]=[CH:2][c:3]1[c:4]([OH:5])[c:6]([Cl:7])[cH:8][c:9]([Br:10])[cH:11]1\"},\"mapped_reaction_smiles\":\"C1N2CN3CN1CN(C2)[CH2:2]3.[OH2:1].[cH:3]1[c:4]([OH:5])[c:6]([Cl:7])[cH:8][c:9]([Br:10])[cH:11]1>O=C(O)C(F)(F)F.O=S(=O)(O)O>[O:1]=[CH:2][c:3]1[c:4]([OH:5])[c:6]([Cl:7])[cH:8][c:9]([Br:10])[cH:11]1\"}",
"reactionStep": {
"id": "sa_805f05fbf76e092166b0ed6d",
"reactionHash": "952fa8f8c9cbee5684515e5f2a99d970aa374b9185970a71733b77d0428d79db"
},
"children": [
{
"id": "12421",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_dd44924b064d87e8c3421f3c",
"parentId": "12420",
"isLeaf": true,
"molecule": {
"id": "sa_dd44924b064d87e8c3421f3c",
"inchikey": "VIBJPUXLAKVICD-UHFFFAOYSA-N",
"smiles": "Oc1ccc(Br)cc1Cl"
},
"smiles": "Oc1ccc(Br)cc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12422",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_911930596f680e19e790270c",
"parentId": "12420",
"isLeaf": true,
"molecule": {
"id": "sa_911930596f680e19e790270c",
"inchikey": "VKYKSIONXSXAKP-UHFFFAOYSA-N",
"smiles": "C1N2CN3CN1CN(C2)C3"
},
"smiles": "C1N2CN3CN1CN(C2)C3",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12423",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_106b35b8a76bbe73829a0a69",
"parentId": "12420",
"isLeaf": true,
"molecule": {
"id": "sa_106b35b8a76bbe73829a0a69",
"inchikey": "XLYOFNOQVPJJNP-UHFFFAOYSA-N",
"smiles": "O"
},
"smiles": "O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "12424",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "12415",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "12425",
"routeId": "sa_d9fd5aaae2257fa84bbaa175",
"moleculeId": "sa_50a8f83dd89c267fbada1205",
"parentId": "12414",
"isLeaf": true,
"molecule": {
"id": "sa_50a8f83dd89c267fbada1205",
"inchikey": "IVRMZWNICZWHMI-UHFFFAOYSA-N",
"smiles": "[N]N=[N-]"
},
"smiles": "[N-]=[N+]=[N-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}