Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(Cc1ccccc1)C(=O)c1cc(NC(=O)c2cc(F)c(F)cc2Cl)[nH]n1
InChiKey
KJXCIARQDXQJQF-UHFFFAOYSA-N
Route Signature
d4f25a737f9385d0b4ca24e835f8eabef83427866dcced74f681e0e7e546607b
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_50092471bc3ee2b6907c61d7",
"signature": "d4f25a737f9385d0b4ca24e835f8eabef83427866dcced74f681e0e7e546607b",
"contentHash": "683e288da884a84a5fc1a594a7b8ad786de5ae5d4475ef937b038a982c54c49a",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_b7e89a89e7aead01d4306701",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00213",
"moleculeId": "sa_5c993a4bbf3a370597e57787",
"smiles": "CN(Cc1ccccc1)C(=O)c1cc(NC(=O)c2cc(F)c(F)cc2Cl)[nH]n1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_5c993a4bbf3a370597e57787",
"inchikey": "KJXCIARQDXQJQF-UHFFFAOYSA-N",
"smiles": "CN(Cc1ccccc1)C(=O)c1cc(NC(=O)c2cc(F)c(F)cc2Cl)[nH]n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "383",
"routeId": "sa_50092471bc3ee2b6907c61d7",
"moleculeId": "sa_5c993a4bbf3a370597e57787",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_5c993a4bbf3a370597e57787",
"inchikey": "KJXCIARQDXQJQF-UHFFFAOYSA-N",
"smiles": "CN(Cc1ccccc1)C(=O)c1cc(NC(=O)c2cc(F)c(F)cc2Cl)[nH]n1"
},
"smiles": "CN(Cc1ccccc1)C(=O)c1cc(NC(=O)c2cc(F)c(F)cc2Cl)[nH]n1",
"reactionStepId": "sa_3adc46bae36576e097704d8d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070032529A1;2320;429705\",\"rsmi\":\"O[C:10](=[O:11])[c:12]1[n:13][nH:14][c:15]([NH:16][C:17](=[O:18])[c:19]2[c:20]([Cl:21])[cH:22][c:23]([F:24])[c:25]([F:26])[cH:27]2)[cH:28]1.[CH3:1][NH:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O.O.O=C(O)O.On1nnc2ccccc21.[Na+].[Na+]>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[c:12]1[n:13][nH:14][c:15]([NH:16][C:17](=[O:18])[c:19]2[c:20]([Cl:21])[cH:22][c:23]([F:24])[c:25]([F:26])[cH:27]2)[cH:28]1\"},\"mapped_reaction_smiles\":\"O[C:10](=[O:11])[c:12]1[n:13][nH:14][c:15]([NH:16][C:17](=[O:18])[c:19]2[c:20]([Cl:21])[cH:22][c:23]([F:24])[c:25]([F:26])[cH:27]2)[cH:28]1.[CH3:1][NH:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O.O.O=C(O)O.On1nnc2ccccc21.[Na+].[Na+]>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[c:12]1[n:13][nH:14][c:15]([NH:16][C:17](=[O:18])[c:19]2[c:20]([Cl:21])[cH:22][c:23]([F:24])[c:25]([F:26])[cH:27]2)[cH:28]1\"}",
"reactionStep": {
"id": "sa_3adc46bae36576e097704d8d",
"reactionHash": "7e1ca95b19f848a7ddc653fc2a3cf6cd8a3cfa0b273cc5a802630db6823f76ff"
},
"children": [
{
"id": "384",
"routeId": "sa_50092471bc3ee2b6907c61d7",
"moleculeId": "sa_e7cc96fd2bfe92e4449ef6ba",
"parentId": "383",
"isLeaf": true,
"molecule": {
"id": "sa_e7cc96fd2bfe92e4449ef6ba",
"inchikey": "RIWRFSMVIUAEBX-UHFFFAOYSA-N",
"smiles": "CNCc1ccccc1"
},
"smiles": "CNCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "385",
"routeId": "sa_50092471bc3ee2b6907c61d7",
"moleculeId": "sa_9f0a35a4d0740eac0cea9faa",
"parentId": "383",
"isLeaf": false,
"molecule": {
"id": "sa_9f0a35a4d0740eac0cea9faa",
"inchikey": "VOJFIWXBBFJKLY-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cc(NC(=O)c2cc(F)c(F)cc2Cl)[nH]n1"
},
"smiles": "O=C(O)c1cc(NC(=O)c2cc(F)c(F)cc2Cl)[nH]n1",
"reactionStepId": "sa_3985f40cdf50826959c7f699",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070032529A1;2188;429676\",\"rsmi\":\"CC[O:3][C:2](=[O:1])[c:4]1[n:5][nH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[c:12]([Cl:13])[cH:14][c:15]([F:16])[c:17]([F:18])[cH:19]2)[cH:20]1>CCO.Cl.O.[Na+].O>[O:1]=[C:2]([OH:3])[c:4]1[n:5][nH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[c:12]([Cl:13])[cH:14][c:15]([F:16])[c:17]([F:18])[cH:19]2)[cH:20]1\"},\"mapped_reaction_smiles\":\"CC[O:3][C:2](=[O:1])[c:4]1[n:5][nH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[c:12]([Cl:13])[cH:14][c:15]([F:16])[c:17]([F:18])[cH:19]2)[cH:20]1>CCO.Cl.O.[Na+].O>[O:1]=[C:2]([OH:3])[c:4]1[n:5][nH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[c:12]([Cl:13])[cH:14][c:15]([F:16])[c:17]([F:18])[cH:19]2)[cH:20]1\"}",
"reactionStep": {
"id": "sa_3985f40cdf50826959c7f699",
"reactionHash": "a8382291d486a0c0ba39921a68b5ced552a4ce4c4e90b411f10c1b64cbda0270"
},
"children": [
{
"id": "386",
"routeId": "sa_50092471bc3ee2b6907c61d7",
"moleculeId": "sa_c95f2926e53f469fee5a0d59",
"parentId": "385",
"isLeaf": false,
"molecule": {
"id": "sa_c95f2926e53f469fee5a0d59",
"inchikey": "GDPROEGWZVAIEF-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc(NC(=O)c2cc(F)c(F)cc2Cl)[nH]n1"
},
"smiles": "CCOC(=O)c1cc(NC(=O)c2cc(F)c(F)cc2Cl)[nH]n1",
"reactionStepId": "sa_ee8da60d0390e2522cd6be97",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070032529A1;2186;429675\",\"rsmi\":\"Cl[C:11](=[O:12])[c:13]1[c:14]([Cl:15])[cH:16][c:17]([F:18])[c:19]([F:20])[cH:21]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][nH:8][c:9]([NH2:10])[cH:22]1>C1CCOC1.c1ccncc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][nH:8][c:9]([NH:10][C:11](=[O:12])[c:13]2[c:14]([Cl:15])[cH:16][c:17]([F:18])[c:19]([F:20])[cH:21]2)[cH:22]1\"},\"mapped_reaction_smiles\":\"Cl[C:11](=[O:12])[c:13]1[c:14]([Cl:15])[cH:16][c:17]([F:18])[c:19]([F:20])[cH:21]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][nH:8][c:9]([NH2:10])[cH:22]1>C1CCOC1.c1ccncc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][nH:8][c:9]([NH:10][C:11](=[O:12])[c:13]2[c:14]([Cl:15])[cH:16][c:17]([F:18])[c:19]([F:20])[cH:21]2)[cH:22]1\"}",
"reactionStep": {
"id": "sa_ee8da60d0390e2522cd6be97",
"reactionHash": "ea4fb0bbdd711ce1d8e27712e25ce57a7b392ad2c0c539cfb1cc761c65816cf1"
},
"children": [
{
"id": "387",
"routeId": "sa_50092471bc3ee2b6907c61d7",
"moleculeId": "sa_db340620b60d08bd4a147541",
"parentId": "386",
"isLeaf": false,
"molecule": {
"id": "sa_db340620b60d08bd4a147541",
"inchikey": "CPQKGGOPHDHAMN-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc(N)[nH]n1"
},
"smiles": "CCOC(=O)c1cc(N)[nH]n1",
"reactionStepId": "sa_825c04d584940f3f668da920",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070032529A1;2184;429674\",\"rsmi\":\"O=[N+:10]([O-])[c:9]1[nH:8][n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11]1>C.C1CCOC1.CCOC(C)=O.[Pd]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][nH:8][c:9]([NH2:10])[cH:11]1\"},\"mapped_reaction_smiles\":\"O=[N+:10]([O-])[c:9]1[nH:8][n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11]1>C.C1CCOC1.CCOC(C)=O.[Pd]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][nH:8][c:9]([NH2:10])[cH:11]1\"}",
"reactionStep": {
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"reactionHash": "738e0fb817b2c3952c99e426465468a930f0c8f778469b6ce2dacdd027e08a83"
},
"children": [
{
"id": "388",
"routeId": "sa_50092471bc3ee2b6907c61d7",
"moleculeId": "sa_588b14c1f825e4637a926035",
"parentId": "387",
"isLeaf": false,
"molecule": {
"id": "sa_588b14c1f825e4637a926035",
"inchikey": "SNZZJCBTYCCHNG-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc([N+](=O)[O-])[nH]n1"
},
"smiles": "CCOC(=O)c1cc([N+](=O)[O-])[nH]n1",
"reactionStepId": "sa_7aaa656e55574b950bb3d5fb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070032529A1;2182;429673\",\"rsmi\":\"O[C:4](=[O:5])[c:6]1[n:7][nH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1.[CH3:1][CH2:2][OH:3]>CS(=O)(=O)O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][nH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1\"},\"mapped_reaction_smiles\":\"O[C:4](=[O:5])[c:6]1[n:7][nH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1.[CH3:1][CH2:2][OH:3]>CS(=O)(=O)O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][nH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_721cc73829dd4e345e24a0f9",
"parentId": "388",
"isLeaf": true,
"molecule": {
"id": "sa_721cc73829dd4e345e24a0f9",
"inchikey": "HKYHBMLIEAMWRO-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cc([N+](=O)[O-])n[nH]1"
},
"smiles": "O=C(O)c1cc([N+](=O)[O-])[nH]n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "390",
"routeId": "sa_50092471bc3ee2b6907c61d7",
"moleculeId": "sa_afaca116b303dc7d01346819",
"parentId": "388",
"isLeaf": true,
"molecule": {
"id": "sa_afaca116b303dc7d01346819",
"inchikey": "LFQSCWFLJHTTHZ-UHFFFAOYSA-N",
"smiles": "CCO"
},
"smiles": "CCO",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
},
{
"id": "391",
"routeId": "sa_50092471bc3ee2b6907c61d7",
"moleculeId": "sa_d8ad5225544a15931cdd63ea",
"parentId": "386",
"isLeaf": false,
"molecule": {
"id": "sa_d8ad5225544a15931cdd63ea",
"inchikey": "WVGSPMZLNNRZRH-UHFFFAOYSA-N",
"smiles": "O=C(Cl)c1cc(F)c(F)cc1Cl"
},
"smiles": "O=C(Cl)c1cc(F)c(F)cc1Cl",
"reactionStepId": "sa_0d245482f2949166c076da56",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070032529A1;2180;429672\",\"rsmi\":\"O=S(Cl)[Cl:3].O[C:2](=[O:1])[c:4]1[c:5]([Cl:6])[cH:7][c:8]([F:9])[c:10]([F:11])[cH:12]1>CN(C)C=O.Cc1ccccc1>[O:1]=[C:2]([Cl:3])[c:4]1[c:5]([Cl:6])[cH:7][c:8]([F:9])[c:10]([F:11])[cH:12]1\"},\"mapped_reaction_smiles\":\"O=S(Cl)[Cl:3].O[C:2](=[O:1])[c:4]1[c:5]([Cl:6])[cH:7][c:8]([F:9])[c:10]([F:11])[cH:12]1>CN(C)C=O.Cc1ccccc1>[O:1]=[C:2]([Cl:3])[c:4]1[c:5]([Cl:6])[cH:7][c:8]([F:9])[c:10]([F:11])[cH:12]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_124a0c2df4fa016dcd07815a",
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"molecule": {
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"inchikey": "CGFMLBSNHNWJAW-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cc(F)c(F)cc1Cl"
},
"smiles": "O=C(O)c1cc(F)c(F)cc1Cl",
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{
"id": "393",
"routeId": "sa_50092471bc3ee2b6907c61d7",
"moleculeId": "sa_cd67ce42f230ef1a4063353c",
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"molecule": {
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"inchikey": "FYSNRJHAOHDILO-UHFFFAOYSA-N",
"smiles": "O=S(Cl)Cl"
},
"smiles": "O=S(Cl)Cl",
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}
]
}
]
}
]
}
]
}
}