Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1ccc(-c2cccc(CO)c2)nc1C(=O)Nc1c(C)cnc(C(=O)O)c1C
InChiKey
BTJMFQSOPOMZHD-UHFFFAOYSA-N
Route Signature
0e5ea696af3122f1a81f8faab12ad6f1cec9707c7f2fc39796d2e40e6854f9ba
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_1791773eb305d734184434ad",
"signature": "0e5ea696af3122f1a81f8faab12ad6f1cec9707c7f2fc39796d2e40e6854f9ba",
"contentHash": "f54d25b4f18e0ff82e8f564f664e3d63161c8434e3a963f942f82ca481ec7be3",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_7db6bb884bd7d786e504b081",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00649",
"moleculeId": "sa_19d4bfa2e2fe711c36a7ec52",
"smiles": "Cc1ccc(-c2cccc(CO)c2)nc1C(=O)Nc1c(C)cnc(C(=O)O)c1C",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_19d4bfa2e2fe711c36a7ec52",
"inchikey": "BTJMFQSOPOMZHD-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2cccc(CO)c2)nc1C(=O)Nc1c(C)cnc(C(=O)O)c1C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9630",
"routeId": "sa_1791773eb305d734184434ad",
"moleculeId": "sa_19d4bfa2e2fe711c36a7ec52",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_19d4bfa2e2fe711c36a7ec52",
"inchikey": "BTJMFQSOPOMZHD-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2cccc(CO)c2)nc1C(=O)Nc1c(C)cnc(C(=O)O)c1C"
},
"smiles": "Cc1ccc(-c2cccc(CO)c2)nc1C(=O)Nc1c(C)cnc(C(=O)O)c1C",
"reactionStepId": "sa_823051e75d5b5cefaa3bc517",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251306A1;0170;1926892\",\"rsmi\":\"CC[O:25][C:23]([c:22]1[c:20]([CH3:21])[c:19]([NH:18][C:16]([c:15]2[c:2]([CH3:1])[cH:3][cH:4][c:5](-[c:6]3[cH:7][c:8]([CH2:9][OH:10])[cH:11][cH:12][cH:13]3)[n:14]2)=[O:17])[c:28]([CH3:29])[cH:27][n:26]1)=[O:24]>C1CCOC1.CO.Cl.O.[Li+].O>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][OH:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]1[C:16](=[O:17])[NH:18][c:19]1[c:20]([CH3:21])[c:22]([C:23](=[O:24])[OH:25])[n:26][cH:27][c:28]1[CH3:29]\"},\"mapped_reaction_smiles\":\"CC[O:25][C:23]([c:22]1[c:20]([CH3:21])[c:19]([NH:18][C:16]([c:15]2[c:2]([CH3:1])[cH:3][cH:4][c:5](-[c:6]3[cH:7][c:8]([CH2:9][OH:10])[cH:11][cH:12][cH:13]3)[n:14]2)=[O:17])[c:28]([CH3:29])[cH:27][n:26]1)=[O:24]>C1CCOC1.CO.Cl.O.[Li+].O>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][OH:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]1[C:16](=[O:17])[NH:18][c:19]1[c:20]([CH3:21])[c:22]([C:23](=[O:24])[OH:25])[n:26][cH:27][c:28]1[CH3:29]\"}",
"reactionStep": {
"id": "sa_823051e75d5b5cefaa3bc517",
"reactionHash": "98c367f25493cbd25c7941037bbf32799548c58eda618f4f26abd5076327d18d"
},
"children": [
{
"id": "9631",
"routeId": "sa_1791773eb305d734184434ad",
"moleculeId": "sa_d46aa94d7a5ceb9b176d8b63",
"parentId": "9630",
"isLeaf": false,
"molecule": {
"id": "sa_d46aa94d7a5ceb9b176d8b63",
"inchikey": "WODIVXFNANYWSZ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ncc(C)c(NC(=O)c2nc(-c3cccc(CO)c3)ccc2C)c1C"
},
"smiles": "CCOC(=O)c1ncc(C)c(NC(=O)c2nc(-c3cccc(CO)c3)ccc2C)c1C",
"reactionStepId": "sa_76c9dbf67b0b636600ec3cce",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251306A1;0168;1926891\",\"rsmi\":\"Cl[c:17]1[n:16][c:15]([C:13]([NH:12][c:11]2[c:9]([CH3:10])[cH:8][n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:30]2[CH3:31])=[O:14])[c:28]([CH3:29])[cH:27][cH:26]1.OB(O)[c:18]1[cH:19][c:20]([CH2:21][OH:22])[cH:23][cH:24][cH:25]1>C1COCCO1.ClCCl.Cl[Pd]Cl.O.O=C(O)O.[Cs+].[Cs+].[Fe+2]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:9]([CH3:10])[c:11]([NH:12][C:13](=[O:14])[c:15]2[n:16][c:17](-[c:18]3[cH:19][c:20]([CH2:21][OH:22])[cH:23][cH:24][cH:25]3)[cH:26][cH:27][c:28]2[CH3:29])[c:30]1[CH3:31]\"},\"mapped_reaction_smiles\":\"Cl[c:17]1[n:16][c:15]([C:13]([NH:12][c:11]2[c:9]([CH3:10])[cH:8][n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:30]2[CH3:31])=[O:14])[c:28]([CH3:29])[cH:27][cH:26]1.OB(O)[c:18]1[cH:19][c:20]([CH2:21][OH:22])[cH:23][cH:24][cH:25]1>C1COCCO1.ClCCl.Cl[Pd]Cl.O.O=C(O)O.[Cs+].[Cs+].[Fe+2]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:9]([CH3:10])[c:11]([NH:12][C:13](=[O:14])[c:15]2[n:16][c:17](-[c:18]3[cH:19][c:20]([CH2:21][OH:22])[cH:23][cH:24][cH:25]3)[cH:26][cH:27][c:28]2[CH3:29])[c:30]1[CH3:31]\"}",
"reactionStep": {
"id": "sa_76c9dbf67b0b636600ec3cce",
"reactionHash": "27c8022d01763662ca832123874542f3b27a996e3d126652656ea60aa30305be"
},
"children": [
{
"id": "9632",
"routeId": "sa_1791773eb305d734184434ad",
"moleculeId": "sa_370011e2080c35e36130e003",
"parentId": "9631",
"isLeaf": true,
"molecule": {
"id": "sa_370011e2080c35e36130e003",
"inchikey": "HGTDLKXUWVKLQX-UHFFFAOYSA-N",
"smiles": "OCc1cccc(B(O)O)c1"
},
"smiles": "OCc1cccc(B(O)O)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9633",
"routeId": "sa_1791773eb305d734184434ad",
"moleculeId": "sa_562fedd779bc1817e966b481",
"parentId": "9631",
"isLeaf": false,
"molecule": {
"id": "sa_562fedd779bc1817e966b481",
"inchikey": "VUSVCWJSTRZWNE-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ncc(C)c(NC(=O)c2nc(Cl)ccc2C)c1C"
},
"smiles": "CCOC(=O)c1ncc(C)c(NC(=O)c2nc(Cl)ccc2C)c1C",
"reactionStepId": "sa_745d755153f44fc0fde0b7c8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251306A1;0166;1926890\",\"rsmi\":\"O[C:13](=[O:14])[c:15]1[n:16][c:17]([Cl:18])[cH:19][cH:20][c:21]1[CH3:22].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:9]([CH3:10])[c:11]([NH2:12])[c:23]1[CH3:24]>C1CCOC1.CC(C)COC(=O)Cl.CN1CCOCC1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:9]([CH3:10])[c:11]([NH:12][C:13](=[O:14])[c:15]2[n:16][c:17]([Cl:18])[cH:19][cH:20][c:21]2[CH3:22])[c:23]1[CH3:24]\"},\"mapped_reaction_smiles\":\"O[C:13](=[O:14])[c:15]1[n:16][c:17]([Cl:18])[cH:19][cH:20][c:21]1[CH3:22].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:9]([CH3:10])[c:11]([NH2:12])[c:23]1[CH3:24]>C1CCOC1.CC(C)COC(=O)Cl.CN1CCOCC1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:9]([CH3:10])[c:11]([NH:12][C:13](=[O:14])[c:15]2[n:16][c:17]([Cl:18])[cH:19][cH:20][c:21]2[CH3:22])[c:23]1[CH3:24]\"}",
"reactionStep": {
"id": "sa_745d755153f44fc0fde0b7c8",
"reactionHash": "fdf0d653560a927bf96e4350f3247819e0e957a8ecb8730879c6e583df972b90"
},
"children": [
{
"id": "9634",
"routeId": "sa_1791773eb305d734184434ad",
"moleculeId": "sa_8dda5f21c403512d37cf4895",
"parentId": "9633",
"isLeaf": false,
"molecule": {
"id": "sa_8dda5f21c403512d37cf4895",
"inchikey": "ODSPBBWQVLWOPG-UHFFFAOYSA-N",
"smiles": "Cc1ccc(Cl)nc1C(=O)O"
},
"smiles": "Cc1ccc(Cl)nc1C(=O)O",
"reactionStepId": "sa_20ec5324e99989b6958cf68a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251306A1;0071;1926858\",\"rsmi\":\"C[O:11][C:9]([c:8]1[c:2]([CH3:1])[cH:3][cH:4][c:5]([Cl:6])[n:7]1)=[O:10]>C1CCOC1.O=C(O)CC(O)(CC(=O)O)C(=O)O.[Na+].O>[CH3:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[n:7][c:8]1[C:9](=[O:10])[OH:11]\"},\"mapped_reaction_smiles\":\"C[O:11][C:9]([c:8]1[c:2]([CH3:1])[cH:3][cH:4][c:5]([Cl:6])[n:7]1)=[O:10]>C1CCOC1.O=C(O)CC(O)(CC(=O)O)C(=O)O.[Na+].O>[CH3:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[n:7][c:8]1[C:9](=[O:10])[OH:11]\"}",
"reactionStep": {
"id": "sa_20ec5324e99989b6958cf68a",
"reactionHash": "84b95f981f836499d612a64f7a004abc118ca752e46269aa625ca3bf5dbf9754"
},
"children": [
{
"id": "9635",
"routeId": "sa_1791773eb305d734184434ad",
"moleculeId": "sa_49ada0487a45b707ecfca5f8",
"parentId": "9634",
"isLeaf": false,
"molecule": {
"id": "sa_49ada0487a45b707ecfca5f8",
"inchikey": "XWPSWOKQWBNRDW-UHFFFAOYSA-N",
"smiles": "COC(=O)c1nc(Cl)ccc1C"
},
"smiles": "COC(=O)c1nc(Cl)ccc1C",
"reactionStepId": "sa_313ef401d059f1cd4b550ca9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251306A1;0069;1926857\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:8].[O-][n+:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]([CH3:12])[cH:10][cH:9][cH:7]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[CH3:12]\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:8].[O-][n+:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]([CH3:12])[cH:10][cH:9][cH:7]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[CH3:12]\"}",
"reactionStep": {
"id": "sa_313ef401d059f1cd4b550ca9",
"reactionHash": "f96aa850d7f52355638c2cfe965bbb3bf65b7f9e22577e1dbf8f293dc3aa48fe"
},
"children": [
{
"id": "9636",
"routeId": "sa_1791773eb305d734184434ad",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "9635",
"isLeaf": true,
"molecule": {
"id": "sa_312a7cd3d48a055e9bc98180",
"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9637",
"routeId": "sa_1791773eb305d734184434ad",
"moleculeId": "sa_06529a5d3213173e2532f2af",
"parentId": "9635",
"isLeaf": true,
"molecule": {
"id": "sa_06529a5d3213173e2532f2af",
"inchikey": "YSRBMUMDFAGAAD-UHFFFAOYSA-N",
"smiles": "COC(=O)c1c(C)ccc[n+]1[O-]"
},
"smiles": "COC(=O)c1c(C)ccc[n+]1[O-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "9638",
"routeId": "sa_1791773eb305d734184434ad",
"moleculeId": "sa_06d835c961d144b98574bf47",
"parentId": "9633",
"isLeaf": false,
"molecule": {
"id": "sa_06d835c961d144b98574bf47",
"inchikey": "VBVQMLNNVXDKAY-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ncc(C)c(N)c1C"
},
"smiles": "CCOC(=O)c1ncc(C)c(N)c1C",
"reactionStepId": "sa_861f1cb306f5325d89d92765",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251306A1;0160;1926887\",\"rsmi\":\"O=[N+:12]([O-])[c:11]1[c:9]([CH3:10])[cH:8][n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:13]1[CH3:14]>CCO.[Pd]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:9]([CH3:10])[c:11]([NH2:12])[c:13]1[CH3:14]\"},\"mapped_reaction_smiles\":\"O=[N+:12]([O-])[c:11]1[c:9]([CH3:10])[cH:8][n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:13]1[CH3:14]>CCO.[Pd]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:9]([CH3:10])[c:11]([NH2:12])[c:13]1[CH3:14]\"}",
"reactionStep": {
"id": "sa_861f1cb306f5325d89d92765",
"reactionHash": "c76c9f4860c1c2dd418bb35f9ce7665f14f073814fef3c61369253bc9ffc149f"
},
"children": [
{
"id": "9639",
"routeId": "sa_1791773eb305d734184434ad",
"moleculeId": "sa_43092c8eb683e0936717e302",
"parentId": "9638",
"isLeaf": true,
"molecule": {
"id": "sa_43092c8eb683e0936717e302",
"inchikey": "NKTOYGQNPAZMDK-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ncc(C)c([N+](=O)[O-])c1C"
},
"smiles": "CCOC(=O)c1ncc(C)c([N+](=O)[O-])c1C",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
]
}
]
}
}