Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)c1onc(-c2c(Cl)cccc2Cl)c1COc1ccc2cc(-c3ccc(C(=O)O)cn3)ccc2c1
InChiKey
DOHWILYQDVZVGX-UHFFFAOYSA-N
Route Signature
58575cdb7c8871764c6c3a9b9b4aaea38e8ac5898c32f4c1815c9caa0082577c
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_3838f8b1dacfae96177bc101",
"signature": "58575cdb7c8871764c6c3a9b9b4aaea38e8ac5898c32f4c1815c9caa0082577c",
"contentHash": "932fc37b7388d652833a97748fe08bf090919cc98d730350b7727b5c8c0c4d67",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_2200a8ba0764b5d60621808f",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01741",
"moleculeId": "sa_9206f451a44b62fff0d7bcf9",
"smiles": "CC(C)c1onc(-c2c(Cl)cccc2Cl)c1COc1ccc2cc(-c3ccc(C(=O)O)cn3)ccc2c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_9206f451a44b62fff0d7bcf9",
"inchikey": "DOHWILYQDVZVGX-UHFFFAOYSA-N",
"smiles": "CC(C)c1onc(-c2c(Cl)cccc2Cl)c1COc1ccc2cc(-c3ccc(C(=O)O)cn3)ccc2c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10427",
"routeId": "sa_3838f8b1dacfae96177bc101",
"moleculeId": "sa_9206f451a44b62fff0d7bcf9",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_9206f451a44b62fff0d7bcf9",
"inchikey": "DOHWILYQDVZVGX-UHFFFAOYSA-N",
"smiles": "CC(C)c1onc(-c2c(Cl)cccc2Cl)c1COc1ccc2cc(-c3ccc(C(=O)O)cn3)ccc2c1"
},
"smiles": "CC(C)c1onc(-c2c(Cl)cccc2Cl)c1COc1ccc2cc(-c3ccc(C(=O)O)cn3)ccc2c1",
"reactionStepId": "sa_26340988a006bb7835edf393",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110034507A1;0655;1012657\",\"rsmi\":\"C[O:20][C:18]([c:17]1[cH:16][cH:15][c:14](-[c:13]2[cH:12][c:11]3[cH:10][cH:9][c:8]([O:7][CH2:6][c:5]4[c:4]([CH:2]([CH3:1])[CH3:3])[o:37][n:36][c:27]4-[c:28]4[c:29]([Cl:30])[cH:31][cH:32][cH:33][c:34]4[Cl:35])[cH:26][c:25]3[cH:24][cH:23]2)[n:22][cH:21]1)=[O:19]>C1CCOC1.CO.[Na+].O>[CH3:1][CH:2]([CH3:3])[c:4]1[c:5]([CH2:6][O:7][c:8]2[cH:9][cH:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][n:22]4)[cH:23][cH:24][c:25]3[cH:26]2)[c:27](-[c:28]2[c:29]([Cl:30])[cH:31][cH:32][cH:33][c:34]2[Cl:35])[n:36][o:37]1\"},\"mapped_reaction_smiles\":\"C[O:20][C:18]([c:17]1[cH:16][cH:15][c:14](-[c:13]2[cH:12][c:11]3[cH:10][cH:9][c:8]([O:7][CH2:6][c:5]4[c:4]([CH:2]([CH3:1])[CH3:3])[o:37][n:36][c:27]4-[c:28]4[c:29]([Cl:30])[cH:31][cH:32][cH:33][c:34]4[Cl:35])[cH:26][c:25]3[cH:24][cH:23]2)[n:22][cH:21]1)=[O:19]>C1CCOC1.CO.[Na+].O>[CH3:1][CH:2]([CH3:3])[c:4]1[c:5]([CH2:6][O:7][c:8]2[cH:9][cH:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][n:22]4)[cH:23][cH:24][c:25]3[cH:26]2)[c:27](-[c:28]2[c:29]([Cl:30])[cH:31][cH:32][cH:33][c:34]2[Cl:35])[n:36][o:37]1\"}",
"reactionStep": {
"id": "sa_26340988a006bb7835edf393",
"reactionHash": "650006c556aeecd3e34911e1a4de03b717bf605d236e64e255ae7c36611feef6"
},
"children": [
{
"id": "10428",
"routeId": "sa_3838f8b1dacfae96177bc101",
"moleculeId": "sa_3b3eb5d2288f165ab13cb710",
"parentId": "10427",
"isLeaf": false,
"molecule": {
"id": "sa_3b3eb5d2288f165ab13cb710",
"inchikey": "JRJYXRRSGQMTRC-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(-c2ccc3cc(OCc4c(-c5c(Cl)cccc5Cl)noc4C(C)C)ccc3c2)nc1"
},
"smiles": "COC(=O)c1ccc(-c2ccc3cc(OCc4c(-c5c(Cl)cccc5Cl)noc4C(C)C)ccc3c2)nc1",
"reactionStepId": "sa_f9439658c53c80d64977e3a4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110034507A1;0653;1012656\",\"rsmi\":\"Cl[CH2:16][c:17]1[c:18]([CH:19]([CH3:20])[CH3:21])[o:22][n:23][c:24]1-[c:25]1[c:26]([Cl:27])[cH:28][cH:29][cH:30][c:31]1[Cl:32].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:33][c:34]3[cH:35][cH:36]2)[n:37][cH:38]1>CCOC(C)=O.CN(C)C=O.O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]4[c:18]([CH:19]([CH3:20])[CH3:21])[o:22][n:23][c:24]4-[c:25]4[c:26]([Cl:27])[cH:28][cH:29][cH:30][c:31]4[Cl:32])[cH:33][c:34]3[cH:35][cH:36]2)[n:37][cH:38]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:16][c:17]1[c:18]([CH:19]([CH3:20])[CH3:21])[o:22][n:23][c:24]1-[c:25]1[c:26]([Cl:27])[cH:28][cH:29][cH:30][c:31]1[Cl:32].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:33][c:34]3[cH:35][cH:36]2)[n:37][cH:38]1>CCOC(C)=O.CN(C)C=O.O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]4[c:18]([CH:19]([CH3:20])[CH3:21])[o:22][n:23][c:24]4-[c:25]4[c:26]([Cl:27])[cH:28][cH:29][cH:30][c:31]4[Cl:32])[cH:33][c:34]3[cH:35][cH:36]2)[n:37][cH:38]1\"}",
"reactionStep": {
"id": "sa_f9439658c53c80d64977e3a4",
"reactionHash": "695c05c2abf93b50cb4715219bab75e4dc2c62fb9a82cf4db4921aa509a94a65"
},
"children": [
{
"id": "10429",
"routeId": "sa_3838f8b1dacfae96177bc101",
"moleculeId": "sa_b4f94e6e2c818a3df64c65be",
"parentId": "10428",
"isLeaf": false,
"molecule": {
"id": "sa_b4f94e6e2c818a3df64c65be",
"inchikey": "JMDLBQMKBBJSKK-UHFFFAOYSA-N",
"smiles": "CC(C)c1onc(-c2c(Cl)cccc2Cl)c1CCl"
},
"smiles": "CC(C)c1onc(-c2c(Cl)cccc2Cl)c1CCl",
"reactionStepId": "sa_92451ca0b424f745635cefe8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110034507A1;0450;1012566\",\"rsmi\":\"O=S(Cl)[Cl:7].O[CH2:6][c:5]1[c:4]([CH:2]([CH3:1])[CH3:3])[o:18][n:17][c:8]1-[c:9]1[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]1[Cl:16]>ClCCl.c1ccc2[nH]nnc2c1>[CH3:1][CH:2]([CH3:3])[c:4]1[c:5]([CH2:6][Cl:7])[c:8](-[c:9]2[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]2[Cl:16])[n:17][o:18]1\"},\"mapped_reaction_smiles\":\"O=S(Cl)[Cl:7].O[CH2:6][c:5]1[c:4]([CH:2]([CH3:1])[CH3:3])[o:18][n:17][c:8]1-[c:9]1[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]1[Cl:16]>ClCCl.c1ccc2[nH]nnc2c1>[CH3:1][CH:2]([CH3:3])[c:4]1[c:5]([CH2:6][Cl:7])[c:8](-[c:9]2[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]2[Cl:16])[n:17][o:18]1\"}",
"reactionStep": {
"id": "sa_92451ca0b424f745635cefe8",
"reactionHash": "946bc610c89b870906754ad89bf2889625090b147d6eecb03cc37562376afed1"
},
"children": [
{
"id": "10430",
"routeId": "sa_3838f8b1dacfae96177bc101",
"moleculeId": "sa_cd67ce42f230ef1a4063353c",
"parentId": "10429",
"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": "10431",
"routeId": "sa_3838f8b1dacfae96177bc101",
"moleculeId": "sa_82d2e210c7892922e3c2c2d5",
"parentId": "10429",
"isLeaf": true,
"molecule": {
"id": "sa_82d2e210c7892922e3c2c2d5",
"inchikey": "QKFSDLYZZTWMQG-UHFFFAOYSA-N",
"smiles": "CC(C)c1onc(-c2c(Cl)cccc2Cl)c1CO"
},
"smiles": "CC(C)c1onc(-c2c(Cl)cccc2Cl)c1CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10432",
"routeId": "sa_3838f8b1dacfae96177bc101",
"moleculeId": "sa_3b7360df22aabc93dfb1ac3e",
"parentId": "10428",
"isLeaf": false,
"molecule": {
"id": "sa_3b7360df22aabc93dfb1ac3e",
"inchikey": "WQAVOPOCJRUSDK-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(-c2ccc3cc(O)ccc3c2)nc1"
},
"smiles": "COC(=O)c1ccc(-c2ccc3cc(O)ccc3c2)nc1",
"reactionStepId": "sa_dce6573d16cdbd2324992e9f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110034507A1;0653;1012655\",\"rsmi\":\"C[O:15][c:14]1[cH:13][cH:12][c:11]2[cH:10][c:9](-[c:8]3[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:21][n:20]3)[cH:19][cH:18][c:17]2[cH:16]1>BrB(Br)Br.ClCCl.[Na+].O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]3[cH:18][cH:19]2)[n:20][cH:21]1\"},\"mapped_reaction_smiles\":\"C[O:15][c:14]1[cH:13][cH:12][c:11]2[cH:10][c:9](-[c:8]3[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:21][n:20]3)[cH:19][cH:18][c:17]2[cH:16]1>BrB(Br)Br.ClCCl.[Na+].O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]3[cH:18][cH:19]2)[n:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_dce6573d16cdbd2324992e9f",
"reactionHash": "613ba91ef6c4ecd3f6c3f075e950f943c3a47a54fe775b76e4f19604f1ee18d1"
},
"children": [
{
"id": "10433",
"routeId": "sa_3838f8b1dacfae96177bc101",
"moleculeId": "sa_70515515d5e584f71782053d",
"parentId": "10432",
"isLeaf": false,
"molecule": {
"id": "sa_70515515d5e584f71782053d",
"inchikey": "GYHJEIULQVGAEY-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(-c2ccc3cc(OC)ccc3c2)nc1"
},
"smiles": "COC(=O)c1ccc(-c2ccc3cc(OC)ccc3c2)nc1",
"reactionStepId": "sa_3a7ed2bf6dd78028aae401b9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110034507A1;0651;1012654\",\"rsmi\":\"O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][c:18]3[cH:19][cH:20]2)[n:21][cH:22]1>O=S(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][c:18]3[cH:19][cH:20]2)[n:21][cH:22]1\"},\"mapped_reaction_smiles\":\"O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][c:18]3[cH:19][cH:20]2)[n:21][cH:22]1>O=S(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][c:18]3[cH:19][cH:20]2)[n:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_3a7ed2bf6dd78028aae401b9",
"reactionHash": "b6647e4065b332756a0d7caeee378608bd7eebd5f9f6235a9c1d01bbbcf1f41a"
},
"children": [
{
"id": "10434",
"routeId": "sa_3838f8b1dacfae96177bc101",
"moleculeId": "sa_302e5db0fd20a23671189f59",
"parentId": "10433",
"isLeaf": false,
"molecule": {
"id": "sa_302e5db0fd20a23671189f59",
"inchikey": "JNJBYIBQSLAUTE-UHFFFAOYSA-N",
"smiles": "COc1ccc2cc(-c3ccc(C(=O)O)cn3)ccc2c1"
},
"smiles": "COc1ccc2cc(-c3ccc(C(=O)O)cn3)ccc2c1",
"reactionStepId": "sa_6838647a160e86cd0bafada8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110034507A1;0649;1012653\",\"rsmi\":\"Br[c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[OH:15])[cH:16][n:17]1.OB(O)[c:8]1[cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][c:20]2[cH:19][cH:18]1>CCOC(C)=O.COCCOC.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([C:13](=[O:14])[OH:15])[cH:16][n:17]3)[cH:18][cH:19][c:20]2[cH:21]1\"},\"mapped_reaction_smiles\":\"Br[c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[OH:15])[cH:16][n:17]1.OB(O)[c:8]1[cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][c:20]2[cH:19][cH:18]1>CCOC(C)=O.COCCOC.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([C:13](=[O:14])[OH:15])[cH:16][n:17]3)[cH:18][cH:19][c:20]2[cH:21]1\"}",
"reactionStep": {
"id": "sa_6838647a160e86cd0bafada8",
"reactionHash": "a06a0fdd58bbd6861b7355940831c3ea4ab848a379f4a901adedf3fb7f1fe9bc"
},
"children": [
{
"id": "10435",
"routeId": "sa_3838f8b1dacfae96177bc101",
"moleculeId": "sa_df546844ce8b2a1f92626497",
"parentId": "10434",
"isLeaf": true,
"molecule": {
"id": "sa_df546844ce8b2a1f92626497",
"inchikey": "GZFAVYWCPSMLCM-UHFFFAOYSA-N",
"smiles": "COc1ccc2cc(B(O)O)ccc2c1"
},
"smiles": "COc1ccc2cc(B(O)O)ccc2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10436",
"routeId": "sa_3838f8b1dacfae96177bc101",
"moleculeId": "sa_692cf75ba380a9670dac287b",
"parentId": "10434",
"isLeaf": true,
"molecule": {
"id": "sa_692cf75ba380a9670dac287b",
"inchikey": "JDJBRMNTXORYEN-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ccc(Br)nc1"
},
"smiles": "O=C(O)c1ccc(Br)nc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10437",
"routeId": "sa_3838f8b1dacfae96177bc101",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "10433",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}