Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cccc2c(Cl)ncc(C(=O)N3CCC3)c12
InChiKey
VFCHUBPCMRIQIM-UHFFFAOYSA-N
Route Signature
f12b56ef583a635c066e46f6ce6234dea2704c3ff50d51f979f7be46b1ccd489
Synthesis route with 8 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_7f12717cdde9803366199956",
"signature": "f12b56ef583a635c066e46f6ce6234dea2704c3ff50d51f979f7be46b1ccd489",
"contentHash": "c32e836661d7807c8b7bb6aed0531f534ad914015863e9666e1bd04b0d9bafc1",
"length": 8,
"isConvergent": false
},
"target": {
"id": "sa_a93b651738aa4c184587c675",
"benchmarkSetId": "a82783729b577c36f2e09a2b6fdd55ae9542aed5546571d67ef9cb74dc21f70a",
"targetId": "n1-00016",
"moleculeId": "sa_e16cb5f94545de3c5327c46d",
"smiles": "Cc1cccc2c(Cl)ncc(C(=O)N3CCC3)c12",
"routeLength": 8,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_e16cb5f94545de3c5327c46d",
"inchikey": "VFCHUBPCMRIQIM-UHFFFAOYSA-N",
"smiles": "Cc1cccc2c(Cl)ncc(C(=O)N3CCC3)c12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "16927",
"routeId": "sa_7f12717cdde9803366199956",
"moleculeId": "sa_e16cb5f94545de3c5327c46d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_e16cb5f94545de3c5327c46d",
"inchikey": "VFCHUBPCMRIQIM-UHFFFAOYSA-N",
"smiles": "Cc1cccc2c(Cl)ncc(C(=O)N3CCC3)c12"
},
"smiles": "Cc1cccc2c(Cl)ncc(C(=O)N3CCC3)c12",
"reactionStepId": "sa_97f38b60df74ce55463b106f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09006442B2;0235;1606109\",\"rsmi\":\"O[C:5]([c:4]1[c:3]2[c:2]([CH3:1])[cH:18][cH:17][cH:16][c:15]2[c:13]([Cl:14])[n:12][cH:11]1)=[O:6].[NH:7]1[CH2:8][CH2:9][CH2:10]1>>[CH3:1][c:2]1[c:3]2[c:4]([C:5](=[O:6])[N:7]3[CH2:8][CH2:9][CH2:10]3)[cH:11][n:12][c:13]([Cl:14])[c:15]2[cH:16][cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"O[C:5]([c:4]1[c:3]2[c:2]([CH3:1])[cH:18][cH:17][cH:16][c:15]2[c:13]([Cl:14])[n:12][cH:11]1)=[O:6].[NH:7]1[CH2:8][CH2:9][CH2:10]1>>[CH3:1][c:2]1[c:3]2[c:4]([C:5](=[O:6])[N:7]3[CH2:8][CH2:9][CH2:10]3)[cH:11][n:12][c:13]([Cl:14])[c:15]2[cH:16][cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_97f38b60df74ce55463b106f",
"reactionHash": "5f611d28c38fd359611a33bdcdac03e2be09229497c79097fe9ab90b118312ba"
},
"children": [
{
"id": "16928",
"routeId": "sa_7f12717cdde9803366199956",
"moleculeId": "sa_3edf2a7ec025f1195f3401ef",
"parentId": "16927",
"isLeaf": true,
"molecule": {
"id": "sa_3edf2a7ec025f1195f3401ef",
"inchikey": "HONIICLYMWZJFZ-UHFFFAOYSA-N",
"smiles": "C1CNC1"
},
"smiles": "C1CNC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "16929",
"routeId": "sa_7f12717cdde9803366199956",
"moleculeId": "sa_25c39e09792d19c6d11f0309",
"parentId": "16927",
"isLeaf": false,
"molecule": {
"id": "sa_25c39e09792d19c6d11f0309",
"inchikey": "QJTFFKMNFYAIAY-UHFFFAOYSA-N",
"smiles": "Cc1cccc2c(Cl)ncc(C(=O)O)c12"
},
"smiles": "Cc1cccc2c(Cl)ncc(C(=O)O)c12",
"reactionStepId": "sa_f4ab48bb11333a2cfa64e2c3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09006442B2;0205;1606096\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:11].O[c:10]1[n:9][cH:8][c:4]([C:5](=[O:6])[OH:7])[c:3]2[c:2]([CH3:1])[cH:15][cH:14][cH:13][c:12]21>>[CH3:1][c:2]1[c:3]2[c:4]([C:5](=[O:6])[OH:7])[cH:8][n:9][c:10]([Cl:11])[c:12]2[cH:13][cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:11].O[c:10]1[n:9][cH:8][c:4]([C:5](=[O:6])[OH:7])[c:3]2[c:2]([CH3:1])[cH:15][cH:14][cH:13][c:12]21>>[CH3:1][c:2]1[c:3]2[c:4]([C:5](=[O:6])[OH:7])[cH:8][n:9][c:10]([Cl:11])[c:12]2[cH:13][cH:14][cH:15]1\"}",
"reactionStep": {
"id": "sa_f4ab48bb11333a2cfa64e2c3",
"reactionHash": "9204f10bca816b8a8a1123ec432433363331daabfaa04b95992b267497566173"
},
"children": [
{
"id": "16930",
"routeId": "sa_7f12717cdde9803366199956",
"moleculeId": "sa_36a6a59c97f92c7560da7651",
"parentId": "16929",
"isLeaf": false,
"molecule": {
"id": "sa_36a6a59c97f92c7560da7651",
"inchikey": "ANUWVBYKFIVUFE-UHFFFAOYSA-N",
"smiles": "Cc1cccc2c(O)ncc(C(=O)O)c12"
},
"smiles": "Cc1cccc2c(O)ncc(C(=O)O)c12",
"reactionStepId": "sa_ffa2811bfce532005e25dcd8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09006442B2;0204;1606095\",\"rsmi\":\"C[O:11][c:10]1[n:9][cH:8][c:4]([C:5](=[O:6])[OH:7])[c:3]2[c:2]([CH3:1])[cH:15][cH:14][cH:13][c:12]21>Br.O>[CH3:1][c:2]1[c:3]2[c:4]([C:5](=[O:6])[OH:7])[cH:8][n:9][c:10]([OH:11])[c:12]2[cH:13][cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"C[O:11][c:10]1[n:9][cH:8][c:4]([C:5](=[O:6])[OH:7])[c:3]2[c:2]([CH3:1])[cH:15][cH:14][cH:13][c:12]21>Br.O>[CH3:1][c:2]1[c:3]2[c:4]([C:5](=[O:6])[OH:7])[cH:8][n:9][c:10]([OH:11])[c:12]2[cH:13][cH:14][cH:15]1\"}",
"reactionStep": {
"id": "sa_ffa2811bfce532005e25dcd8",
"reactionHash": "5a8c47826cbdd55942adeb639bf401e28749a938c8e919a2b3f4b66fb459a849"
},
"children": [
{
"id": "16931",
"routeId": "sa_7f12717cdde9803366199956",
"moleculeId": "sa_3f56107465199772bdba29ef",
"parentId": "16930",
"isLeaf": false,
"molecule": {
"id": "sa_3f56107465199772bdba29ef",
"inchikey": "BHJFHAZTKHYDPF-UHFFFAOYSA-N",
"smiles": "COc1ncc(C(=O)O)c2c(C)cccc12"
},
"smiles": "COc1ncc(C(=O)O)c2c(C)cccc12",
"reactionStepId": "sa_93ca31535dab1da88d7b3341",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09006442B2;0203;1606094\",\"rsmi\":\"[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH:7]=[O:8])[c:10]2[c:11]([CH3:12])[cH:13][cH:14][cH:15][c:16]12.[OH2:9]>CC#N.[Na+].[O-][Cl+]O>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]2[c:11]([CH3:12])[cH:13][cH:14][cH:15][c:16]12\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH:7]=[O:8])[c:10]2[c:11]([CH3:12])[cH:13][cH:14][cH:15][c:16]12.[OH2:9]>CC#N.[Na+].[O-][Cl+]O>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]2[c:11]([CH3:12])[cH:13][cH:14][cH:15][c:16]12\"}",
"reactionStep": {
"id": "sa_93ca31535dab1da88d7b3341",
"reactionHash": "10c75cdd2288f37e5ced75ad510b1ebb955a3a222b37b34c0e7dd4968a3f1b75"
},
"children": [
{
"id": "16932",
"routeId": "sa_7f12717cdde9803366199956",
"moleculeId": "sa_106b35b8a76bbe73829a0a69",
"parentId": "16931",
"isLeaf": true,
"molecule": {
"id": "sa_106b35b8a76bbe73829a0a69",
"inchikey": "XLYOFNOQVPJJNP-UHFFFAOYSA-N",
"smiles": "O"
},
"smiles": "O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "16933",
"routeId": "sa_7f12717cdde9803366199956",
"moleculeId": "sa_ef2081124cdca2bc9fa8a1b3",
"parentId": "16931",
"isLeaf": false,
"molecule": {
"id": "sa_ef2081124cdca2bc9fa8a1b3",
"inchikey": "ZDFYJGDMHUXLRC-UHFFFAOYSA-N",
"smiles": "COc1ncc(C=O)c2c(C)cccc12"
},
"smiles": "COc1ncc(C=O)c2c(C)cccc12",
"reactionStepId": "sa_fba5f2d370f46f8ad1ce25b4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09006442B2;0202;1606093\",\"rsmi\":\"Br[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[c:15]2[c:9]1[c:10]([CH3:11])[cH:12][cH:13][cH:14]2.CN(C)[CH:7]=[O:8]>C1CCOC1.[Li]CCCC>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH:7]=[O:8])[c:9]2[c:10]([CH3:11])[cH:12][cH:13][cH:14][c:15]12\"},\"mapped_reaction_smiles\":\"Br[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[c:15]2[c:9]1[c:10]([CH3:11])[cH:12][cH:13][cH:14]2.CN(C)[CH:7]=[O:8]>C1CCOC1.[Li]CCCC>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH:7]=[O:8])[c:9]2[c:10]([CH3:11])[cH:12][cH:13][cH:14][c:15]12\"}",
"reactionStep": {
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"reactionHash": "3244614d8f5d8785b951f0708d4423127197440a450acc693f7cd6a9eba014d6"
},
"children": [
{
"id": "16934",
"routeId": "sa_7f12717cdde9803366199956",
"moleculeId": "sa_79d92a71428c5921ff7bfa05",
"parentId": "16933",
"isLeaf": false,
"molecule": {
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"inchikey": "XZVXRCUVHKRLOQ-UHFFFAOYSA-N",
"smiles": "COc1ncc(Br)c2c(C)cccc12"
},
"smiles": "COc1ncc(Br)c2c(C)cccc12",
"reactionStepId": "sa_6577f9ec34e47eaa5bb3cee8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09006442B2;0201;1606092\",\"rsmi\":\"Cl[c:3]1[n:4][cH:5][c:6]([Br:7])[c:8]2[c:9]([CH3:10])[cH:11][cH:12][cH:13][c:14]12.[CH3:1][OH:2]>CO.[Na+]>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([Br:7])[c:8]2[c:9]([CH3:10])[cH:11][cH:12][cH:13][c:14]12\"},\"mapped_reaction_smiles\":\"Cl[c:3]1[n:4][cH:5][c:6]([Br:7])[c:8]2[c:9]([CH3:10])[cH:11][cH:12][cH:13][c:14]12.[CH3:1][OH:2]>CO.[Na+]>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([Br:7])[c:8]2[c:9]([CH3:10])[cH:11][cH:12][cH:13][c:14]12\"}",
"reactionStep": {
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"reactionHash": "fe2338b3cb909ac3598c8426449df39ef1e886a21c6d629290ecbb97a376f5ff"
},
"children": [
{
"id": "16935",
"routeId": "sa_7f12717cdde9803366199956",
"moleculeId": "sa_13cfa2b044742efa3f37eb96",
"parentId": "16934",
"isLeaf": false,
"molecule": {
"id": "sa_13cfa2b044742efa3f37eb96",
"inchikey": "OIEHDAQHUXWPSL-UHFFFAOYSA-N",
"smiles": "Cc1cccc2c(Cl)ncc(Br)c12"
},
"smiles": "Cc1cccc2c(Cl)ncc(Br)c12",
"reactionStepId": "sa_9bf39bd1db85423b806cd541",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09006442B2;0200;1606091\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:9].O=[c:8]1[nH:7][cH:6][c:4]([Br:5])[c:3]2[c:2]([CH3:1])[cH:13][cH:12][cH:11][c:10]21>>[CH3:1][c:2]1[c:3]2[c:4]([Br:5])[cH:6][n:7][c:8]([Cl:9])[c:10]2[cH:11][cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:9].O=[c:8]1[nH:7][cH:6][c:4]([Br:5])[c:3]2[c:2]([CH3:1])[cH:13][cH:12][cH:11][c:10]21>>[CH3:1][c:2]1[c:3]2[c:4]([Br:5])[cH:6][n:7][c:8]([Cl:9])[c:10]2[cH:11][cH:12][cH:13]1\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"inchikey": "VSJHFWDYFQTNCW-UHFFFAOYSA-N",
"smiles": "Cc1cccc2c(=O)[nH]cc(Br)c12"
},
"smiles": "Cc1cccc2c(=O)[nH]cc(Br)c12",
"reactionStepId": "sa_5778e95ba16336c631749ff3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09006442B2;0199;1606090\",\"rsmi\":\"Br[Br:5].[CH3:1][c:2]1[c:3]2[cH:4][cH:6][nH:7][c:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13]1>CCOCC.ClCCl>[CH3:1][c:2]1[c:3]2[c:4]([Br:5])[cH:6][nH:7][c:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"Br[Br:5].[CH3:1][c:2]1[c:3]2[cH:4][cH:6][nH:7][c:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13]1>CCOCC.ClCCl>[CH3:1][c:2]1[c:3]2[c:4]([Br:5])[cH:6][nH:7][c:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13]1\"}",
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"children": [
{
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"molecule": {
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"inchikey": "GDTBXPJZTBHREO-UHFFFAOYSA-N",
"smiles": "BrBr"
},
"smiles": "BrBr",
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"metadata": null,
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},
{
"id": "16938",
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"molecule": {
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"inchikey": "WSXOURRQDMFDRD-UHFFFAOYSA-N",
"smiles": "Cc1cccc2c(O)nccc12"
},
"smiles": "Cc1cccc2c(=O)[nH]ccc12",
"reactionStepId": null,
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}
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},
{
"id": "16939",
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"molecule": {
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"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
"template": null,
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}
]
},
{
"id": "16940",
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"molecule": {
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"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
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}
]
},
{
"id": "16941",
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"moleculeId": "sa_e0b5e93d36242e79e81ef68c",
"parentId": "16933",
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"molecule": {
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"inchikey": "ZMXDDKWLCZADIW-UHFFFAOYSA-N",
"smiles": "CN(C)C=O"
},
"smiles": "CN(C)C=O",
"reactionStepId": null,
"template": null,
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"children": []
}
]
}
]
}
]
},
{
"id": "16942",
"routeId": "sa_7f12717cdde9803366199956",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "16929",
"isLeaf": true,
"molecule": {
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"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": []
}
]
}
]
}
}