Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(=O)N1CCOC(C(=O)Nc2cc(-c3cccc4[nH]ccc34)cc3[nH]ncc23)C1
InChiKey
LRUKXNUIEMBGKI-UHFFFAOYSA-N
Route Signature
7de901a656eab4dfb74b72ee59c26a8c39fbcd57a6c47f1d94865308f750c634
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_d448e74155de3909bcfc8ebc",
"signature": "7de901a656eab4dfb74b72ee59c26a8c39fbcd57a6c47f1d94865308f750c634",
"contentHash": "9388194a893a8fc1ee6012752747adf0244dba7086cadee8760699c8ec3d97f9",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_de147681bf86d93b9bb19085",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-00947",
"moleculeId": "sa_df824e86ee403507e7da581b",
"smiles": "CC(=O)N1CCOC(C(=O)Nc2cc(-c3cccc4[nH]ccc34)cc3[nH]ncc23)C1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_df824e86ee403507e7da581b",
"inchikey": "LRUKXNUIEMBGKI-UHFFFAOYSA-N",
"smiles": "CC(=O)N1CCOC(C(=O)Nc2cc(-c3cccc4[nH]ccc34)cc3[nH]ncc23)C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "1279",
"routeId": "sa_d448e74155de3909bcfc8ebc",
"moleculeId": "sa_df824e86ee403507e7da581b",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_df824e86ee403507e7da581b",
"inchikey": "LRUKXNUIEMBGKI-UHFFFAOYSA-N",
"smiles": "CC(=O)N1CCOC(C(=O)Nc2cc(-c3cccc4[nH]ccc34)cc3[nH]ncc23)C1"
},
"smiles": "CC(=O)N1CCOC(C(=O)Nc2cc(-c3cccc4[nH]ccc34)cc3[nH]ncc23)C1",
"reactionStepId": "sa_1ec11165cf91f1b0317e9830",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08536169B2;0420;1365653\",\"rsmi\":\"O[C:9]([CH:8]1[O:7][CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:30]1)=[O:10].[NH2:11][c:12]1[c:13]2[cH:14][n:15][nH:16][c:17]2[cH:18][c:19](-[c:20]2[c:21]3[cH:22][cH:23][nH:24][c:25]3[cH:26][cH:27][cH:28]2)[cH:29]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][O:7][CH:8]([C:9](=[O:10])[NH:11][c:12]2[c:13]3[cH:14][n:15][nH:16][c:17]3[cH:18][c:19](-[c:20]3[c:21]4[cH:22][cH:23][nH:24][c:25]4[cH:26][cH:27][cH:28]3)[cH:29]2)[CH2:30]1\"},\"mapped_reaction_smiles\":\"O[C:9]([CH:8]1[O:7][CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:30]1)=[O:10].[NH2:11][c:12]1[c:13]2[cH:14][n:15][nH:16][c:17]2[cH:18][c:19](-[c:20]2[c:21]3[cH:22][cH:23][nH:24][c:25]3[cH:26][cH:27][cH:28]2)[cH:29]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][O:7][CH:8]([C:9](=[O:10])[NH:11][c:12]2[c:13]3[cH:14][n:15][nH:16][c:17]3[cH:18][c:19](-[c:20]3[c:21]4[cH:22][cH:23][nH:24][c:25]4[cH:26][cH:27][cH:28]3)[cH:29]2)[CH2:30]1\"}",
"reactionStep": {
"id": "sa_1ec11165cf91f1b0317e9830",
"reactionHash": "56ab9dd280c5d415b679232939c8d20e9f87623bfd3ae046de94f071e9d65a52"
},
"children": [
{
"id": "1280",
"routeId": "sa_d448e74155de3909bcfc8ebc",
"moleculeId": "sa_17a94a1eb75fea03eab9b29a",
"parentId": "1279",
"isLeaf": false,
"molecule": {
"id": "sa_17a94a1eb75fea03eab9b29a",
"inchikey": "AIBGZQZEONQZCF-UHFFFAOYSA-N",
"smiles": "Nc1cc(-c2cccc3[nH]ccc23)cc2[nH]ncc12"
},
"smiles": "Nc1cc(-c2cccc3[nH]ccc23)cc2[nH]ncc12",
"reactionStepId": "sa_cd2ea0420973cfe45c799744",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08536169B2;0370;1365640\",\"rsmi\":\"Br[c:4]1[cH:3][c:2]([NH2:1])[c:16]2[c:15]([cH:14]1)[nH:19][n:18][cH:17]2.CC1(C)OB([c:5]2[c:6]3[cH:7][cH:8][nH:9][c:10]3[cH:11][cH:12][cH:13]2)OC1(C)C>C1COCCO1.ClCCl.ClCCl.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[Na+].[Na+]>[NH2:1][c:2]1[cH:3][c:4](-[c:5]2[c:6]3[cH:7][cH:8][nH:9][c:10]3[cH:11][cH:12][cH:13]2)[cH:14][c:15]2[c:16]1[cH:17][n:18][nH:19]2\"},\"mapped_reaction_smiles\":\"Br[c:4]1[cH:3][c:2]([NH2:1])[c:16]2[c:15]([cH:14]1)[nH:19][n:18][cH:17]2.CC1(C)OB([c:5]2[c:6]3[cH:7][cH:8][nH:9][c:10]3[cH:11][cH:12][cH:13]2)OC1(C)C>C1COCCO1.ClCCl.ClCCl.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[Na+].[Na+]>[NH2:1][c:2]1[cH:3][c:4](-[c:5]2[c:6]3[cH:7][cH:8][nH:9][c:10]3[cH:11][cH:12][cH:13]2)[cH:14][c:15]2[c:16]1[cH:17][n:18][nH:19]2\"}",
"reactionStep": {
"id": "sa_cd2ea0420973cfe45c799744",
"reactionHash": "ef828e3d81c42f6db8c6f090979d4788b0e6fbcce81fa4d636b4dec92a84e82d"
},
"children": [
{
"id": "1281",
"routeId": "sa_d448e74155de3909bcfc8ebc",
"moleculeId": "sa_7d1fb39fc3816db3b442226e",
"parentId": "1280",
"isLeaf": true,
"molecule": {
"id": "sa_7d1fb39fc3816db3b442226e",
"inchikey": "JORDVWJEXMDSBI-UHFFFAOYSA-N",
"smiles": "Nc1cc(Br)cc2[nH]ncc12"
},
"smiles": "Nc1cc(Br)cc2[nH]ncc12",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1282",
"routeId": "sa_d448e74155de3909bcfc8ebc",
"moleculeId": "sa_8da454c67215591176323435",
"parentId": "1280",
"isLeaf": true,
"molecule": {
"id": "sa_8da454c67215591176323435",
"inchikey": "QDCIXBBEUHMLDN-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cccc3[nH]ccc23)OC1(C)C"
},
"smiles": "CC1(C)OB(c2cccc3[nH]ccc23)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "1283",
"routeId": "sa_d448e74155de3909bcfc8ebc",
"moleculeId": "sa_f547b04a0f2f462d009e9ed5",
"parentId": "1279",
"isLeaf": false,
"molecule": {
"id": "sa_f547b04a0f2f462d009e9ed5",
"inchikey": "ZRKDVLAKXLCMKC-UHFFFAOYSA-N",
"smiles": "CC(=O)N1CCOC(C(=O)O)C1"
},
"smiles": "CC(=O)N1CCOC(C(=O)O)C1",
"reactionStepId": "sa_bd52b5791eddd4578ec00af9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08536169B2;0382;1365644\",\"rsmi\":\"c1ccc(C[O:11][C:9]([CH:8]2[O:7][CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:12]2)=[O:10])cc1>CCO.[Pd]>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][O:7][CH:8]([C:9](=[O:10])[OH:11])[CH2:12]1\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:11][C:9]([CH:8]2[O:7][CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:12]2)=[O:10])cc1>CCO.[Pd]>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][O:7][CH:8]([C:9](=[O:10])[OH:11])[CH2:12]1\"}",
"reactionStep": {
"id": "sa_bd52b5791eddd4578ec00af9",
"reactionHash": "c198035fba9dfc2315349df9a85039205ecd1e84a2c7f6ff1ba86a172becdb8b"
},
"children": [
{
"id": "1284",
"routeId": "sa_d448e74155de3909bcfc8ebc",
"moleculeId": "sa_4a1b84d7a9dcabac8f38c5e5",
"parentId": "1283",
"isLeaf": false,
"molecule": {
"id": "sa_4a1b84d7a9dcabac8f38c5e5",
"inchikey": "JXEHATHFMXZSHL-UHFFFAOYSA-N",
"smiles": "CC(=O)N1CCOC(C(=O)OCc2ccccc2)C1"
},
"smiles": "CC(=O)N1CCOC(C(=O)OCc2ccccc2)C1",
"reactionStepId": "sa_b9d32dacbddd8f29bb74c842",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08536169B2;0379;1365643\",\"rsmi\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[NH:4]1[CH2:5][CH2:6][O:7][CH:8]([C:9](=[O:10])[O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1>CCN(C(C)C)C(C)C.ClCCl>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][O:7][CH:8]([C:9](=[O:10])[O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1\"},\"mapped_reaction_smiles\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[NH:4]1[CH2:5][CH2:6][O:7][CH:8]([C:9](=[O:10])[O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1>CCN(C(C)C)C(C)C.ClCCl>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][O:7][CH:8]([C:9](=[O:10])[O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1\"}",
"reactionStep": {
"id": "sa_b9d32dacbddd8f29bb74c842",
"reactionHash": "7672a066639163f2a1b4db1dd915cd35a95a5e81536f31c29a0b6ae4fab74e61"
},
"children": [
{
"id": "1285",
"routeId": "sa_d448e74155de3909bcfc8ebc",
"moleculeId": "sa_26e4459d757463b9d61a7d97",
"parentId": "1284",
"isLeaf": false,
"molecule": {
"id": "sa_26e4459d757463b9d61a7d97",
"inchikey": "KSDSLTGLIGWVHY-UHFFFAOYSA-N",
"smiles": "O=C(OCc1ccccc1)C1CNCCO1"
},
"smiles": "O=C(OCc1ccccc1)C1CNCCO1",
"reactionStepId": "sa_ed65caaa75101843c46fd18e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08536169B2;0376;1365642\",\"rsmi\":\"CC(C)(C)OC(=O)[N:13]1[CH2:12][CH:11]([C:2](=[O:1])[O:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[O:16][CH2:15][CH2:14]1>C1COCCO1.Cl>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[CH:11]1[CH2:12][NH:13][CH2:14][CH2:15][O:16]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:13]1[CH2:12][CH:11]([C:2](=[O:1])[O:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[O:16][CH2:15][CH2:14]1>C1COCCO1.Cl>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[CH:11]1[CH2:12][NH:13][CH2:14][CH2:15][O:16]1\"}",
"reactionStep": {
"id": "sa_ed65caaa75101843c46fd18e",
"reactionHash": "d64d1828c6d2feb7de391b7291ea40c61854590add529ccac50ab9ebd5b3f247"
},
"children": [
{
"id": "1286",
"routeId": "sa_d448e74155de3909bcfc8ebc",
"moleculeId": "sa_2b6faf5259baaa4e60f2d0ad",
"parentId": "1285",
"isLeaf": false,
"molecule": {
"id": "sa_2b6faf5259baaa4e60f2d0ad",
"inchikey": "ZIHWSJMSQSMTOW-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCOC(C(=O)OCc2ccccc2)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CCOC(C(=O)OCc2ccccc2)C1",
"reactionStepId": "sa_30234b6a68bcca5e7af17a05",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08536169B2;0373;1365641\",\"rsmi\":\"Br[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][O:11][CH:12]([C:13](=[O:14])[OH:15])[CH2:23]1>CN(C)C=O.ClCCl.O.O=C(O)O.[K+].[K+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][O:11][CH:12]([C:13](=[O:14])[O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1\"},\"mapped_reaction_smiles\":\"Br[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][O:11][CH:12]([C:13](=[O:14])[OH:15])[CH2:23]1>CN(C)C=O.ClCCl.O.O=C(O)O.[K+].[K+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][O:11][CH:12]([C:13](=[O:14])[O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1\"}",
"reactionStep": {
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"reactionHash": "b759db6dc89a4ce059e613aaf2ecf05c4689e4e29a44efc384fc480b273f5c76"
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"children": [
{
"id": "1287",
"routeId": "sa_d448e74155de3909bcfc8ebc",
"moleculeId": "sa_4ff2e4de9d80150de333c065",
"parentId": "1286",
"isLeaf": true,
"molecule": {
"id": "sa_4ff2e4de9d80150de333c065",
"inchikey": "AGEZXYOZHKGVCM-UHFFFAOYSA-N",
"smiles": "BrCc1ccccc1"
},
"smiles": "BrCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "1288",
"routeId": "sa_d448e74155de3909bcfc8ebc",
"moleculeId": "sa_b9eebaf153d67a1b2f3b4e82",
"parentId": "1286",
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"molecule": {
"id": "sa_b9eebaf153d67a1b2f3b4e82",
"inchikey": "LGWMTRPJZFEWCX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCOC(C(=O)O)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CCOC(C(=O)O)C1",
"reactionStepId": null,
"template": null,
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}
]
}
]
},
{
"id": "1289",
"routeId": "sa_d448e74155de3909bcfc8ebc",
"moleculeId": "sa_a7893fcf81826693d9b4bed4",
"parentId": "1284",
"isLeaf": true,
"molecule": {
"id": "sa_a7893fcf81826693d9b4bed4",
"inchikey": "WFDIJRYMOXRFFG-UHFFFAOYSA-N",
"smiles": "CC(=O)OC(C)=O"
},
"smiles": "CC(=O)OC(C)=O",
"reactionStepId": null,
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"metadata": null,
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}
]
}
]
}
]
}
}