Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cc(-c2ncc(C)o2)cc(OCc2ccccc2)c1B(O)O
InChiKey
JWOCIQZJFZPYNP-UHFFFAOYSA-N
Route Signature
b058d0697f6bc1225b5461edbb706b723b75795d1ae29b03cd36286cf2fa45d2
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_c11989da3ad61cedf13036ac",
"signature": "b058d0697f6bc1225b5461edbb706b723b75795d1ae29b03cd36286cf2fa45d2",
"contentHash": "ee3460eb7a22b03bf470a2fd785089230d97f75ec87f0d94545ef78959d8db7e",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_611053f07f392b67420a3613",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00297",
"moleculeId": "sa_e45290693e05c90bd423db02",
"smiles": "COc1cc(-c2ncc(C)o2)cc(OCc2ccccc2)c1B(O)O",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_e45290693e05c90bd423db02",
"inchikey": "JWOCIQZJFZPYNP-UHFFFAOYSA-N",
"smiles": "COc1cc(-c2ncc(C)o2)cc(OCc2ccccc2)c1B(O)O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "3916",
"routeId": "sa_c11989da3ad61cedf13036ac",
"moleculeId": "sa_e45290693e05c90bd423db02",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_e45290693e05c90bd423db02",
"inchikey": "JWOCIQZJFZPYNP-UHFFFAOYSA-N",
"smiles": "COc1cc(-c2ncc(C)o2)cc(OCc2ccccc2)c1B(O)O"
},
"smiles": "COc1cc(-c2ncc(C)o2)cc(OCc2ccccc2)c1B(O)O",
"reactionStepId": "sa_d177e3d0ba4b5d1f50b9f2d1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140206661A1;0289;1553453\",\"rsmi\":\"Br[c:22]1[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]2[n:7][cH:8][c:9]([CH3:10])[o:11]2)[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.CO[B:23]([O:24]C)[O:25]C>C1CCOC1.[Li]CCCC>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][cH:8][c:9]([CH3:10])[o:11]2)[cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22]1[B:23]([OH:24])[OH:25]\"},\"mapped_reaction_smiles\":\"Br[c:22]1[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]2[n:7][cH:8][c:9]([CH3:10])[o:11]2)[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.CO[B:23]([O:24]C)[O:25]C>C1CCOC1.[Li]CCCC>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][cH:8][c:9]([CH3:10])[o:11]2)[cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22]1[B:23]([OH:24])[OH:25]\"}",
"reactionStep": {
"id": "sa_d177e3d0ba4b5d1f50b9f2d1",
"reactionHash": "fe6018391173c9b2010c46be98216ebf2507390b669da9f56d716d5c4d3740c9"
},
"children": [
{
"id": "3917",
"routeId": "sa_c11989da3ad61cedf13036ac",
"moleculeId": "sa_c7219d000ca9e3983757fd00",
"parentId": "3916",
"isLeaf": false,
"molecule": {
"id": "sa_c7219d000ca9e3983757fd00",
"inchikey": "PQIIPMJJAHRHHZ-UHFFFAOYSA-N",
"smiles": "COc1cc(-c2ncc(C)o2)cc(OCc2ccccc2)c1Br"
},
"smiles": "COc1cc(-c2ncc(C)o2)cc(OCc2ccccc2)c1Br",
"reactionStepId": "sa_2e334795379cff25b491affb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140206661A1;0288;1553452\",\"rsmi\":\"[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([NH:7][CH2:8][C:9]#[CH:10])=[O:11])[cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22]1[Br:23]>C1COCCO1.[HH].[Na+]>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][cH:8][c:9]([CH3:10])[o:11]2)[cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22]1[Br:23]\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([NH:7][CH2:8][C:9]#[CH:10])=[O:11])[cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22]1[Br:23]>C1COCCO1.[HH].[Na+]>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][cH:8][c:9]([CH3:10])[o:11]2)[cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22]1[Br:23]\"}",
"reactionStep": {
"id": "sa_2e334795379cff25b491affb",
"reactionHash": "f7fc3e044e5d068de471dc60bad71b08562b5ccaf790c220dc94dae6eb268fea"
},
"children": [
{
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"routeId": "sa_c11989da3ad61cedf13036ac",
"moleculeId": "sa_049088680bdc4fad22584bdd",
"parentId": "3917",
"isLeaf": false,
"molecule": {
"id": "sa_049088680bdc4fad22584bdd",
"inchikey": "AIAHLCLRDWZWHQ-UHFFFAOYSA-N",
"smiles": "C#CCNC(=O)c1cc(OC)c(Br)c(OCc2ccccc2)c1"
},
"smiles": "C#CCNC(=O)c1cc(OC)c(Br)c(OCc2ccccc2)c1",
"reactionStepId": "sa_f2a8aedf3f43bb938785c425",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140206661A1;0287;1553451\",\"rsmi\":\"O[C:5](=[O:6])[c:7]1[cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]([Br:19])[c:20]([O:21][CH3:22])[cH:23]1.[CH:1]#[C:2][CH2:3][NH2:4]>CCN(CC)CC.CCOCC.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl>[CH:1]#[C:2][CH2:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]([Br:19])[c:20]([O:21][CH3:22])[cH:23]1\"},\"mapped_reaction_smiles\":\"O[C:5](=[O:6])[c:7]1[cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]([Br:19])[c:20]([O:21][CH3:22])[cH:23]1.[CH:1]#[C:2][CH2:3][NH2:4]>CCN(CC)CC.CCOCC.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl>[CH:1]#[C:2][CH2:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]([Br:19])[c:20]([O:21][CH3:22])[cH:23]1\"}",
"reactionStep": {
"id": "sa_f2a8aedf3f43bb938785c425",
"reactionHash": "8df12636036158cbebfa5fddfe8f44971489e11bf626a97145fd3329553b5de4"
},
"children": [
{
"id": "3919",
"routeId": "sa_c11989da3ad61cedf13036ac",
"moleculeId": "sa_7adb0aeae0b4e92531ef2292",
"parentId": "3918",
"isLeaf": true,
"molecule": {
"id": "sa_7adb0aeae0b4e92531ef2292",
"inchikey": "JKANAVGODYYCQF-UHFFFAOYSA-N",
"smiles": "C#CCN"
},
"smiles": "C#CCN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3920",
"routeId": "sa_c11989da3ad61cedf13036ac",
"moleculeId": "sa_d8f97a8595fe0cff6b6b901d",
"parentId": "3918",
"isLeaf": false,
"molecule": {
"id": "sa_d8f97a8595fe0cff6b6b901d",
"inchikey": "UNEMEBDSEHTYDH-UHFFFAOYSA-N",
"smiles": "COc1cc(C(=O)O)cc(OCc2ccccc2)c1Br"
},
"smiles": "COc1cc(C(=O)O)cc(OCc2ccccc2)c1Br",
"reactionStepId": "sa_fc2faaa46b4c5322b218c9e2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140206661A1;0286;1553450\",\"rsmi\":\"C[O:8][C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:19]([Br:20])[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:9]1)=[O:7]>C1CCOC1.CO.[Na+].O>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]1[Br:20]\"},\"mapped_reaction_smiles\":\"C[O:8][C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:19]([Br:20])[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:9]1)=[O:7]>C1CCOC1.CO.[Na+].O>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]1[Br:20]\"}",
"reactionStep": {
"id": "sa_fc2faaa46b4c5322b218c9e2",
"reactionHash": "935a5699f37978ee0ceb49383cbe3d52b2a3d9aec6dea20dc4c4e49179d3eed2"
},
"children": [
{
"id": "3921",
"routeId": "sa_c11989da3ad61cedf13036ac",
"moleculeId": "sa_f80d0ea0be1a9e880eb575fc",
"parentId": "3920",
"isLeaf": false,
"molecule": {
"id": "sa_f80d0ea0be1a9e880eb575fc",
"inchikey": "BYYVXSILTNDSEQ-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(OC)c(Br)c(OCc2ccccc2)c1"
},
"smiles": "COC(=O)c1cc(OC)c(Br)c(OCc2ccccc2)c1",
"reactionStepId": "sa_396e3f738d7ccf85a4c02a00",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140206661A1;0285;1553449\",\"rsmi\":\"I[CH3:20].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]([Br:17])[c:18]([OH:19])[cH:21]1>CN(C)C=O.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]([Br:17])[c:18]([O:19][CH3:20])[cH:21]1\"},\"mapped_reaction_smiles\":\"I[CH3:20].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]([Br:17])[c:18]([OH:19])[cH:21]1>CN(C)C=O.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]([Br:17])[c:18]([O:19][CH3:20])[cH:21]1\"}",
"reactionStep": {
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"reactionHash": "aa808c53ca495416941230c492e3f2370765b17202225781eaf07ef6de656b39"
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"children": [
{
"id": "3922",
"routeId": "sa_c11989da3ad61cedf13036ac",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
"parentId": "3921",
"isLeaf": true,
"molecule": {
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"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "3923",
"routeId": "sa_c11989da3ad61cedf13036ac",
"moleculeId": "sa_5a64fc520b4b9eacb480501e",
"parentId": "3921",
"isLeaf": false,
"molecule": {
"id": "sa_5a64fc520b4b9eacb480501e",
"inchikey": "NCWXIIHXWQKDFT-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(O)c(Br)c(OCc2ccccc2)c1"
},
"smiles": "COC(=O)c1cc(O)c(Br)c(OCc2ccccc2)c1",
"reactionStepId": "sa_71e0473e46d1d289ad2a41b3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140206661A1;0284;1553448\",\"rsmi\":\"Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([OH:8])[c:16]([Br:17])[c:18]([OH:19])[cH:20]1>CN(C)C=O.Cl.ClCCl.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]([Br:17])[c:18]([OH:19])[cH:20]1\"},\"mapped_reaction_smiles\":\"Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([OH:8])[c:16]([Br:17])[c:18]([OH:19])[cH:20]1>CN(C)C=O.Cl.ClCCl.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]([Br:17])[c:18]([OH:19])[cH:20]1\"}",
"reactionStep": {
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"reactionHash": "803c7b53abc7855f7024da7f71cdb74438c702f1a6773688f659065fa47f1294"
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"children": [
{
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"routeId": "sa_c11989da3ad61cedf13036ac",
"moleculeId": "sa_4ff2e4de9d80150de333c065",
"parentId": "3923",
"isLeaf": true,
"molecule": {
"id": "sa_4ff2e4de9d80150de333c065",
"inchikey": "AGEZXYOZHKGVCM-UHFFFAOYSA-N",
"smiles": "BrCc1ccccc1"
},
"smiles": "BrCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "3925",
"routeId": "sa_c11989da3ad61cedf13036ac",
"moleculeId": "sa_f6dba918ae3e24edce812a0d",
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"molecule": {
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"inchikey": "UXSHRKILYILVSD-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(O)c(Br)c(O)c1"
},
"smiles": "COC(=O)c1cc(O)c(Br)c(O)c1",
"reactionStepId": null,
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}
]
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]
}
]
}
]
}
]
},
{
"id": "3926",
"routeId": "sa_c11989da3ad61cedf13036ac",
"moleculeId": "sa_3921eda8cccff81eb2f5828f",
"parentId": "3916",
"isLeaf": true,
"molecule": {
"id": "sa_3921eda8cccff81eb2f5828f",
"inchikey": "WRECIMRULFAWHA-UHFFFAOYSA-N",
"smiles": "COB(OC)OC"
},
"smiles": "COB(OC)OC",
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"children": []
}
]
}
}