Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cccc2c(Cl)ncc(C(=O)NCC3CCOCC3)c12
InChiKey
YIEJDKKWLVTREK-UHFFFAOYSA-N
Route Signature
61054542c72c757ac560247e2edc264647ffbe2c9220abe60f86d6889c6d80dc
Synthesis route with 8 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_eab6d5471ffe612b3ac61ce9",
"signature": "61054542c72c757ac560247e2edc264647ffbe2c9220abe60f86d6889c6d80dc",
"contentHash": "4146d487aa166238884a56f5cd4d9a271688fdc43bc58c543b9e0546789b1f02",
"length": 8,
"isConvergent": false
},
"target": {
"id": "sa_dbb4265cc7c9933d5b174535",
"benchmarkSetId": "a82783729b577c36f2e09a2b6fdd55ae9542aed5546571d67ef9cb74dc21f70a",
"targetId": "n5-00115",
"moleculeId": "sa_468ff3b27c7e6113bf93ecb9",
"smiles": "Cc1cccc2c(Cl)ncc(C(=O)NCC3CCOCC3)c12",
"routeLength": 8,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_468ff3b27c7e6113bf93ecb9",
"inchikey": "YIEJDKKWLVTREK-UHFFFAOYSA-N",
"smiles": "Cc1cccc2c(Cl)ncc(C(=O)NCC3CCOCC3)c12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "17718",
"routeId": "sa_eab6d5471ffe612b3ac61ce9",
"moleculeId": "sa_468ff3b27c7e6113bf93ecb9",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_468ff3b27c7e6113bf93ecb9",
"inchikey": "YIEJDKKWLVTREK-UHFFFAOYSA-N",
"smiles": "Cc1cccc2c(Cl)ncc(C(=O)NCC3CCOCC3)c12"
},
"smiles": "Cc1cccc2c(Cl)ncc(C(=O)NCC3CCOCC3)c12",
"reactionStepId": "sa_5e9c20440e044bbcf633eec4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130178457A1;0186;1390382\",\"rsmi\":\"O[C:5]([c:4]1[c:3]2[c:2]([CH3:1])[cH:22][cH:21][cH:20][c:19]2[c:17]([Cl:18])[n:16][cH:15]1)=[O:6].[NH2:7][CH2:8][CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1>>[CH3:1][c:2]1[c:3]2[c:4]([C:5](=[O:6])[NH:7][CH2:8][CH:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)[cH:15][n:16][c:17]([Cl:18])[c:19]2[cH:20][cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"O[C:5]([c:4]1[c:3]2[c:2]([CH3:1])[cH:22][cH:21][cH:20][c:19]2[c:17]([Cl:18])[n:16][cH:15]1)=[O:6].[NH2:7][CH2:8][CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1>>[CH3:1][c:2]1[c:3]2[c:4]([C:5](=[O:6])[NH:7][CH2:8][CH:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)[cH:15][n:16][c:17]([Cl:18])[c:19]2[cH:20][cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_5e9c20440e044bbcf633eec4",
"reactionHash": "ed2d26885221c999a122c43f4b7c794b5ef59afaecf0e2cb4a6104a2505347c9"
},
"children": [
{
"id": "17719",
"routeId": "sa_eab6d5471ffe612b3ac61ce9",
"moleculeId": "sa_93cd08a663a4d32d9f72a383",
"parentId": "17718",
"isLeaf": true,
"molecule": {
"id": "sa_93cd08a663a4d32d9f72a383",
"inchikey": "IPBPLHNLRKRLPJ-UHFFFAOYSA-N",
"smiles": "NCC1CCOCC1"
},
"smiles": "NCC1CCOCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "17720",
"routeId": "sa_eab6d5471ffe612b3ac61ce9",
"moleculeId": "sa_25c39e09792d19c6d11f0309",
"parentId": "17718",
"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\":\"US20130178457A1;0182;1390381\",\"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": [
{
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"routeId": "sa_eab6d5471ffe612b3ac61ce9",
"moleculeId": "sa_36a6a59c97f92c7560da7651",
"parentId": "17720",
"isLeaf": false,
"molecule": {
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"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\":\"US20130178457A1;0181;1390380\",\"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": "17722",
"routeId": "sa_eab6d5471ffe612b3ac61ce9",
"moleculeId": "sa_3f56107465199772bdba29ef",
"parentId": "17721",
"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\":\"US20130178457A1;0180;1390379\",\"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": {
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"reactionHash": "10c75cdd2288f37e5ced75ad510b1ebb955a3a222b37b34c0e7dd4968a3f1b75"
},
"children": [
{
"id": "17723",
"routeId": "sa_eab6d5471ffe612b3ac61ce9",
"moleculeId": "sa_106b35b8a76bbe73829a0a69",
"parentId": "17722",
"isLeaf": true,
"molecule": {
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"inchikey": "XLYOFNOQVPJJNP-UHFFFAOYSA-N",
"smiles": "O"
},
"smiles": "O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "17724",
"routeId": "sa_eab6d5471ffe612b3ac61ce9",
"moleculeId": "sa_ef2081124cdca2bc9fa8a1b3",
"parentId": "17722",
"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\":\"US20130178457A1;0179;1390378\",\"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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"children": [
{
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"routeId": "sa_eab6d5471ffe612b3ac61ce9",
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"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\":\"US20130178457A1;0178;1390377\",\"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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"children": [
{
"id": "17726",
"routeId": "sa_eab6d5471ffe612b3ac61ce9",
"moleculeId": "sa_13cfa2b044742efa3f37eb96",
"parentId": "17725",
"isLeaf": false,
"molecule": {
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"inchikey": "OIEHDAQHUXWPSL-UHFFFAOYSA-N",
"smiles": "Cc1cccc2c(Cl)ncc(Br)c12"
},
"smiles": "Cc1cccc2c(Cl)ncc(Br)c12",
"reactionStepId": "sa_9bf39bd1db85423b806cd541",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130178457A1;0177;1390376\",\"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\":\"US20130178457A1;0176;1390375\",\"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",
"reactionStepId": null,
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"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "17729",
"routeId": "sa_eab6d5471ffe612b3ac61ce9",
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"molecule": {
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"smiles": "Cc1cccc2c(O)nccc12"
},
"smiles": "Cc1cccc2c(=O)[nH]ccc12",
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}
]
},
{
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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,
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}
]
},
{
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"molecule": {
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"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
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"children": []
}
]
},
{
"id": "17732",
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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": "17733",
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"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": []
}
]
}
]
}
}