Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1ccc(-c2cc(C#N)c(OC(C)c3ccc(F)cc3)nc2-c2ccc(Cl)cc2Cl)cc1
InChiKey
BGHKQLWJOSXJKW-UHFFFAOYSA-N
Route Signature
0051b758426f8afc2595bf250ebedf9cea0cf50966e2f4df5cd8b064fb5acab9
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_f1342c1efea838a3939c0648",
"signature": "0051b758426f8afc2595bf250ebedf9cea0cf50966e2f4df5cd8b064fb5acab9",
"contentHash": "7cb6bf5b40fc247d7e330add9189ed21d27c298b1ecaa57e8a62b9626165027b",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_fe2a2799d53baa369578bc97",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00553",
"moleculeId": "sa_3d644ed254baacdabf06d8e7",
"smiles": "Cc1ccc(-c2cc(C#N)c(OC(C)c3ccc(F)cc3)nc2-c2ccc(Cl)cc2Cl)cc1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_3d644ed254baacdabf06d8e7",
"inchikey": "BGHKQLWJOSXJKW-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2cc(C#N)c(OC(C)c3ccc(F)cc3)nc2-c2ccc(Cl)cc2Cl)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "4478",
"routeId": "sa_f1342c1efea838a3939c0648",
"moleculeId": "sa_3d644ed254baacdabf06d8e7",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_3d644ed254baacdabf06d8e7",
"inchikey": "BGHKQLWJOSXJKW-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2cc(C#N)c(OC(C)c3ccc(F)cc3)nc2-c2ccc(Cl)cc2Cl)cc1"
},
"smiles": "Cc1ccc(-c2cc(C#N)c(OC(C)c3ccc(F)cc3)nc2-c2ccc(Cl)cc2Cl)cc1",
"reactionStepId": "sa_4ab58782c39c8fcbb7398e28",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07271266B2;1335;806183\",\"rsmi\":\"Cl[c:11]1[c:8]([C:9]#[N:10])[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:33][cH:32]2)[c:23](-[c:24]2[c:25]([Cl:26])[cH:27][c:28]([Cl:29])[cH:30][cH:31]2)[n:22]1.[OH:12][CH:13]([CH3:14])[c:15]1[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]1>Cc1ccccc1.O=C(O)O.[Cs+].[Cs+]>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9]#[N:10])[c:11]([O:12][CH:13]([CH3:14])[c:15]3[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]3)[n:22][c:23]2-[c:24]2[c:25]([Cl:26])[cH:27][c:28]([Cl:29])[cH:30][cH:31]2)[cH:32][cH:33]1\"},\"mapped_reaction_smiles\":\"Cl[c:11]1[c:8]([C:9]#[N:10])[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:33][cH:32]2)[c:23](-[c:24]2[c:25]([Cl:26])[cH:27][c:28]([Cl:29])[cH:30][cH:31]2)[n:22]1.[OH:12][CH:13]([CH3:14])[c:15]1[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]1>Cc1ccccc1.O=C(O)O.[Cs+].[Cs+]>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9]#[N:10])[c:11]([O:12][CH:13]([CH3:14])[c:15]3[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]3)[n:22][c:23]2-[c:24]2[c:25]([Cl:26])[cH:27][c:28]([Cl:29])[cH:30][cH:31]2)[cH:32][cH:33]1\"}",
"reactionStep": {
"id": "sa_4ab58782c39c8fcbb7398e28",
"reactionHash": "ec8d5409c2c2a78dd034f127df8be52853f2615c1b67f2dfe11ea6c763f5134e"
},
"children": [
{
"id": "4479",
"routeId": "sa_f1342c1efea838a3939c0648",
"moleculeId": "sa_2ae8eabd9e68c38f4d9f996a",
"parentId": "4478",
"isLeaf": true,
"molecule": {
"id": "sa_2ae8eabd9e68c38f4d9f996a",
"inchikey": "PSDSORRYQPTKSV-UHFFFAOYSA-N",
"smiles": "CC(O)c1ccc(F)cc1"
},
"smiles": "CC(O)c1ccc(F)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4480",
"routeId": "sa_f1342c1efea838a3939c0648",
"moleculeId": "sa_74da12e7247976dd487e5c55",
"parentId": "4478",
"isLeaf": false,
"molecule": {
"id": "sa_74da12e7247976dd487e5c55",
"inchikey": "WWEBTCYXHWIIOG-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2cc(C#N)c(Cl)nc2-c2ccc(Cl)cc2Cl)cc1"
},
"smiles": "Cc1ccc(-c2cc(C#N)c(Cl)nc2-c2ccc(Cl)cc2Cl)cc1",
"reactionStepId": "sa_c7b683227246f38f73765a22",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07271266B2;1333;806182\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:12].O=[c:11]1[c:8]([C:9]#[N:10])[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:24][cH:23]2)[c:14](-[c:15]2[c:16]([Cl:17])[cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[nH:13]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9]#[N:10])[c:11]([Cl:12])[n:13][c:14]2-[c:15]2[c:16]([Cl:17])[cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:12].O=[c:11]1[c:8]([C:9]#[N:10])[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:24][cH:23]2)[c:14](-[c:15]2[c:16]([Cl:17])[cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[nH:13]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9]#[N:10])[c:11]([Cl:12])[n:13][c:14]2-[c:15]2[c:16]([Cl:17])[cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_c7b683227246f38f73765a22",
"reactionHash": "0678af48255c1cac92218d4d1f2c7f06ac5f4abd16204ead8fbcd90870a3235f"
},
"children": [
{
"id": "4481",
"routeId": "sa_f1342c1efea838a3939c0648",
"moleculeId": "sa_e16c7984aff83cc532b69203",
"parentId": "4480",
"isLeaf": false,
"molecule": {
"id": "sa_e16c7984aff83cc532b69203",
"inchikey": "VQLAJNIICNWTNY-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2cc(C#N)c(=O)[nH]c2-c2ccc(Cl)cc2Cl)cc1"
},
"smiles": "Cc1ccc(-c2cc(C#N)c(=O)[nH]c2-c2ccc(Cl)cc2Cl)cc1",
"reactionStepId": "sa_a4d84d8c0b199ca9b4ec5e19",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07271266B2;1331;806181\",\"rsmi\":\"CN(C)[CH:22]=[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:24][cH:23]1)[C:7](=O)[c:8]1[c:9]([Cl:10])[cH:11][c:12]([Cl:13])[cH:14][cH:15]1.[NH2:16][C:17](=[O:18])[CH2:19][C:20]#[N:21]>CN(C)C=O.CO.[HH].[Na+]>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7](-[c:8]3[c:9]([Cl:10])[cH:11][c:12]([Cl:13])[cH:14][cH:15]3)[nH:16][c:17](=[O:18])[c:19]([C:20]#[N:21])[cH:22]2)[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"CN(C)[CH:22]=[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:24][cH:23]1)[C:7](=O)[c:8]1[c:9]([Cl:10])[cH:11][c:12]([Cl:13])[cH:14][cH:15]1.[NH2:16][C:17](=[O:18])[CH2:19][C:20]#[N:21]>CN(C)C=O.CO.[HH].[Na+]>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7](-[c:8]3[c:9]([Cl:10])[cH:11][c:12]([Cl:13])[cH:14][cH:15]3)[nH:16][c:17](=[O:18])[c:19]([C:20]#[N:21])[cH:22]2)[cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_a4d84d8c0b199ca9b4ec5e19",
"reactionHash": "e66851822cdddc4748487709f668a5a310382d57b3f375632f677c2759719dc6"
},
"children": [
{
"id": "4482",
"routeId": "sa_f1342c1efea838a3939c0648",
"moleculeId": "sa_f621d53165070dfbfd540bf2",
"parentId": "4481",
"isLeaf": true,
"molecule": {
"id": "sa_f621d53165070dfbfd540bf2",
"inchikey": "DGJMPUGMZIKDRO-UHFFFAOYSA-N",
"smiles": "N#CCC(=N)O"
},
"smiles": "N#CCC(N)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4483",
"routeId": "sa_f1342c1efea838a3939c0648",
"moleculeId": "sa_2a1e383e9cf6260e409d84d5",
"parentId": "4481",
"isLeaf": false,
"molecule": {
"id": "sa_2a1e383e9cf6260e409d84d5",
"inchikey": "JZFSPVMIZPMLCE-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C(=CN(C)C)C(=O)c2ccc(Cl)cc2Cl)cc1"
},
"smiles": "Cc1ccc(C(=CN(C)C)C(=O)c2ccc(Cl)cc2Cl)cc1",
"reactionStepId": "sa_097d4338bb78506ee2862475",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07271266B2;1329;806180\",\"rsmi\":\"CO[CH:7](OC)[N:8]([CH3:9])[CH3:10].[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][C:11](=[O:12])[c:13]2[c:14]([Cl:15])[cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[cH:21][cH:22]1>CN(C)C=O>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[CH:7][N:8]([CH3:9])[CH3:10])[C:11](=[O:12])[c:13]2[c:14]([Cl:15])[cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"CO[CH:7](OC)[N:8]([CH3:9])[CH3:10].[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][C:11](=[O:12])[c:13]2[c:14]([Cl:15])[cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[cH:21][cH:22]1>CN(C)C=O>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[CH:7][N:8]([CH3:9])[CH3:10])[C:11](=[O:12])[c:13]2[c:14]([Cl:15])[cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[cH:21][cH:22]1\"}",
"reactionStep": {
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"reactionHash": "9ab539806b4f34ec25a8ef11bfeb30fe9b1b75a39699f9771247c1b8e7fc668a"
},
"children": [
{
"id": "4484",
"routeId": "sa_f1342c1efea838a3939c0648",
"moleculeId": "sa_87cb58dd8fb69a7facf2ef2e",
"parentId": "4483",
"isLeaf": false,
"molecule": {
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"inchikey": "LXPPZGDPKTYJPE-UHFFFAOYSA-N",
"smiles": "Cc1ccc(CC(=O)c2ccc(Cl)cc2Cl)cc1"
},
"smiles": "Cc1ccc(CC(=O)c2ccc(Cl)cc2Cl)cc1",
"reactionStepId": "sa_62b2c52fb304783197be18c7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07271266B2;1327;806179\",\"rsmi\":\"Br[CH2:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:18][cH:17]1.CC[O:8]CC.N#[C:7][c:9]1[c:10]([Cl:11])[cH:12][c:13]([Cl:14])[cH:15][cH:16]1>[Mg]>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][C:7](=[O:8])[c:9]2[c:10]([Cl:11])[cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"Br[CH2:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:18][cH:17]1.CC[O:8]CC.N#[C:7][c:9]1[c:10]([Cl:11])[cH:12][c:13]([Cl:14])[cH:15][cH:16]1>[Mg]>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][C:7](=[O:8])[c:9]2[c:10]([Cl:11])[cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[cH:17][cH:18]1\"}",
"reactionStep": {
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"reactionHash": "a1e3e7447fdfcd24a1bd583e19ec9b93e2bdfb8e3a4b3f8090caa241c2670b3f"
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"children": [
{
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"moleculeId": "sa_4abc00ba2bf4f0e982cd19d4",
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"molecule": {
"id": "sa_4abc00ba2bf4f0e982cd19d4",
"inchikey": "GRUHREVRSOOQJG-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(Cl)cc1Cl"
},
"smiles": "N#Cc1ccc(Cl)cc1Cl",
"reactionStepId": null,
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},
{
"id": "4486",
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"molecule": {
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"inchikey": "RTZKZFJDLAIYFH-UHFFFAOYSA-N",
"smiles": "CCOCC"
},
"smiles": "CCOCC",
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},
{
"id": "4487",
"routeId": "sa_f1342c1efea838a3939c0648",
"moleculeId": "sa_5a2643419f9f10e194c803fc",
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"molecule": {
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"inchikey": "WZRKSPFYXUXINF-UHFFFAOYSA-N",
"smiles": "Cc1ccc(CBr)cc1"
},
"smiles": "Cc1ccc(CBr)cc1",
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}
]
},
{
"id": "4488",
"routeId": "sa_f1342c1efea838a3939c0648",
"moleculeId": "sa_d78fcb876b2dc2bc451d189d",
"parentId": "4483",
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"molecule": {
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"inchikey": "ZSXGLVDWWRXATF-UHFFFAOYSA-N",
"smiles": "COC(OC)N(C)C"
},
"smiles": "COC(OC)N(C)C",
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}
]
}
]
},
{
"id": "4489",
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"molecule": {
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"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
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}
]
}
]
}
}