Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(NCC1(N2CCCCC2)CC(CO)C1)c1ccc(Cl)cc1Cl
InChiKey
JXIVLCPNKAQBOC-UHFFFAOYSA-N
Route Signature
c2b520fbf495db314cd17f843ac95013182faab165344fb6fb4d4552d6421f7b
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_47375f170850dbebf4b03c18",
"signature": "c2b520fbf495db314cd17f843ac95013182faab165344fb6fb4d4552d6421f7b",
"contentHash": "e6cad9406a23f3e6ddc323502b767bdbd705b3cac2819a89c926cf8db0dc62fe",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_1a24a6b275e728aeda214d0f",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00136",
"moleculeId": "sa_a5c7737cfbc82f8a009a8dbc",
"smiles": "O=C(NCC1(N2CCCCC2)CC(CO)C1)c1ccc(Cl)cc1Cl",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_a5c7737cfbc82f8a009a8dbc",
"inchikey": "JXIVLCPNKAQBOC-UHFFFAOYSA-N",
"smiles": "O=C(NCC1(N2CCCCC2)CC(CO)C1)c1ccc(Cl)cc1Cl"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12538",
"routeId": "sa_47375f170850dbebf4b03c18",
"moleculeId": "sa_a5c7737cfbc82f8a009a8dbc",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_a5c7737cfbc82f8a009a8dbc",
"inchikey": "JXIVLCPNKAQBOC-UHFFFAOYSA-N",
"smiles": "O=C(NCC1(N2CCCCC2)CC(CO)C1)c1ccc(Cl)cc1Cl"
},
"smiles": "O=C(NCC1(N2CCCCC2)CC(CO)C1)c1ccc(Cl)cc1Cl",
"reactionStepId": "sa_41634dab0604a16fd81dbe19",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100222317A1;0241;936508\",\"rsmi\":\"c1ccc(C[O:15][CH2:14][CH:13]2[CH2:12][C:5]([CH2:4][NH:3][C:2](=[O:1])[c:17]3[c:18]([Cl:19])[cH:20][c:21]([Cl:22])[cH:23][cH:24]3)([N:6]3[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]3)[CH2:16]2)cc1>C[Si](C)(C)I.ClCCl>[O:1]=[C:2]([NH:3][CH2:4][C:5]1([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:12][CH:13]([CH2:14][OH:15])[CH2:16]1)[c:17]1[c:18]([Cl:19])[cH:20][c:21]([Cl:22])[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:15][CH2:14][CH:13]2[CH2:12][C:5]([CH2:4][NH:3][C:2](=[O:1])[c:17]3[c:18]([Cl:19])[cH:20][c:21]([Cl:22])[cH:23][cH:24]3)([N:6]3[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]3)[CH2:16]2)cc1>C[Si](C)(C)I.ClCCl>[O:1]=[C:2]([NH:3][CH2:4][C:5]1([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:12][CH:13]([CH2:14][OH:15])[CH2:16]1)[c:17]1[c:18]([Cl:19])[cH:20][c:21]([Cl:22])[cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_41634dab0604a16fd81dbe19",
"reactionHash": "6958a6cf5acce67eaf9df3cda0dfe246e5768d9c4b76f3534af8858c74eedfe8"
},
"children": [
{
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"routeId": "sa_47375f170850dbebf4b03c18",
"moleculeId": "sa_52ec04d8a3c399dcf6feb1ea",
"parentId": "12538",
"isLeaf": false,
"molecule": {
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"inchikey": "HBECVEDUZKPDGV-UHFFFAOYSA-N",
"smiles": "O=C(NCC1(N2CCCCC2)CC(COCc2ccccc2)C1)c1ccc(Cl)cc1Cl"
},
"smiles": "O=C(NCC1(N2CCCCC2)CC(COCc2ccccc2)C1)c1ccc(Cl)cc1Cl",
"reactionStepId": "sa_d7d90bbd29f0c1f5c3d09e32",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100222317A1;0240;936507\",\"rsmi\":\"Cl[C:2](=[O:1])[c:24]1[c:25]([Cl:26])[cH:27][c:28]([Cl:29])[cH:30][cH:31]1.[NH2:3][CH2:4][C:5]1([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:12][CH:13]([CH2:14][O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1>CCN(C(C)C)C(C)C.ClCCl.O>[O:1]=[C:2]([NH:3][CH2:4][C:5]1([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:12][CH:13]([CH2:14][O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1)[c:24]1[c:25]([Cl:26])[cH:27][c:28]([Cl:29])[cH:30][cH:31]1\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[c:24]1[c:25]([Cl:26])[cH:27][c:28]([Cl:29])[cH:30][cH:31]1.[NH2:3][CH2:4][C:5]1([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:12][CH:13]([CH2:14][O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1>CCN(C(C)C)C(C)C.ClCCl.O>[O:1]=[C:2]([NH:3][CH2:4][C:5]1([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:12][CH:13]([CH2:14][O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1)[c:24]1[c:25]([Cl:26])[cH:27][c:28]([Cl:29])[cH:30][cH:31]1\"}",
"reactionStep": {
"id": "sa_d7d90bbd29f0c1f5c3d09e32",
"reactionHash": "2b19d6d14d546cba4e3f2dfeb54be4bce8af8166029842cea920ae7a908535f6"
},
"children": [
{
"id": "12540",
"routeId": "sa_47375f170850dbebf4b03c18",
"moleculeId": "sa_ff1560d4352549acc244e039",
"parentId": "12539",
"isLeaf": true,
"molecule": {
"id": "sa_ff1560d4352549acc244e039",
"inchikey": "CEOCVKWBUWKBKA-UHFFFAOYSA-N",
"smiles": "O=C(Cl)c1ccc(Cl)cc1Cl"
},
"smiles": "O=C(Cl)c1ccc(Cl)cc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12541",
"routeId": "sa_47375f170850dbebf4b03c18",
"moleculeId": "sa_5f0b3db3373b947a1ee58de7",
"parentId": "12539",
"isLeaf": false,
"molecule": {
"id": "sa_5f0b3db3373b947a1ee58de7",
"inchikey": "CGULGYDOOJOSNV-UHFFFAOYSA-N",
"smiles": "NCC1(N2CCCCC2)CC(COCc2ccccc2)C1"
},
"smiles": "NCC1(N2CCCCC2)CC(COCc2ccccc2)C1",
"reactionStepId": "sa_d0578b954ab7fa7a749d550d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100222317A1;0239;936506\",\"rsmi\":\"[N:1]#[C:2][C:3]1([N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:10][CH:11]([CH2:12][O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21]1>CCOCC.O.[Al+3].[HH].[HH].[HH].[HH].[Li+].[Na+].O>[NH2:1][CH2:2][C:3]1([N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:10][CH:11]([CH2:12][O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21]1\"},\"mapped_reaction_smiles\":\"[N:1]#[C:2][C:3]1([N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:10][CH:11]([CH2:12][O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21]1>CCOCC.O.[Al+3].[HH].[HH].[HH].[HH].[Li+].[Na+].O>[NH2:1][CH2:2][C:3]1([N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:10][CH:11]([CH2:12][O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21]1\"}",
"reactionStep": {
"id": "sa_d0578b954ab7fa7a749d550d",
"reactionHash": "402e7e9846962c68ae12842d116305412b9438bfb18e4e0566eb0126adf8657e"
},
"children": [
{
"id": "12542",
"routeId": "sa_47375f170850dbebf4b03c18",
"moleculeId": "sa_210f088dbb38f46f2a0a6c41",
"parentId": "12541",
"isLeaf": false,
"molecule": {
"id": "sa_210f088dbb38f46f2a0a6c41",
"inchikey": "QYFPEBKICVBYFM-UHFFFAOYSA-N",
"smiles": "N#CC1(N2CCCCC2)CC(COCc2ccccc2)C1"
},
"smiles": "N#CC1(N2CCCCC2)CC(COCc2ccccc2)C1",
"reactionStepId": "sa_2ffa93aad3db734c619b98ee",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100222317A1;0238;936505\",\"rsmi\":\"O=[C:3]1[CH2:10][CH:11]([CH2:12][O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21]1.[N:1]#[CH:2].[NH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1>CCOC(C)=O.CO.Cl.O=C(O)O.[Na+].[Na+].[Na+]>[N:1]#[C:2][C:3]1([N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:10][CH:11]([CH2:12][O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21]1\"},\"mapped_reaction_smiles\":\"O=[C:3]1[CH2:10][CH:11]([CH2:12][O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21]1.[N:1]#[CH:2].[NH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1>CCOC(C)=O.CO.Cl.O=C(O)O.[Na+].[Na+].[Na+]>[N:1]#[C:2][C:3]1([N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:10][CH:11]([CH2:12][O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21]1\"}",
"reactionStep": {
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"reactionHash": "54173a87edb55a2085a017ef998c43ec2997e5ece5c662c3cf0e498693d42d44"
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"children": [
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"routeId": "sa_47375f170850dbebf4b03c18",
"moleculeId": "sa_5ff19d31a8b4b44b6c103ad4",
"parentId": "12542",
"isLeaf": false,
"molecule": {
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"inchikey": "FHBBBGYOVFMVIB-UHFFFAOYSA-N",
"smiles": "O=C1CC(COCc2ccccc2)C1"
},
"smiles": "O=C1CC(COCc2ccccc2)C1",
"reactionStepId": "sa_a87bd8aa91340b38cfea5687",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100222317A1;0237;936504\",\"rsmi\":\"Cl[C:3]1(Cl)[C:2](=[O:1])[CH2:14][CH:4]1[CH2:5][O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>CO.[Zn]>[O:1]=[C:2]1[CH2:3][CH:4]([CH2:5][O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14]1\"},\"mapped_reaction_smiles\":\"Cl[C:3]1(Cl)[C:2](=[O:1])[CH2:14][CH:4]1[CH2:5][O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>CO.[Zn]>[O:1]=[C:2]1[CH2:3][CH:4]([CH2:5][O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14]1\"}",
"reactionStep": {
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"children": [
{
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"routeId": "sa_47375f170850dbebf4b03c18",
"moleculeId": "sa_0989ebb9efa95d33be25393e",
"parentId": "12543",
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"molecule": {
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"inchikey": "HTBVHBZQWJHYRI-UHFFFAOYSA-N",
"smiles": "O=C1CC(COCc2ccccc2)C1(Cl)Cl"
},
"smiles": "O=C1CC(COCc2ccccc2)C1(Cl)Cl",
"reactionStepId": "sa_3891040b91aff1598fab76a0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100222317A1;0236;936503\",\"rsmi\":\"Cl[C:2](=[O:1])[C:14](Cl)([Cl:15])[Cl:16].[CH2:3]=[CH:4][CH2:5][O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>CCOCC.COCCOC.[Cu].[Zn]>[O:1]=[C:2]1[CH2:3][CH:4]([CH2:5][O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[C:14]1([Cl:15])[Cl:16]\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[C:14](Cl)([Cl:15])[Cl:16].[CH2:3]=[CH:4][CH2:5][O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>CCOCC.COCCOC.[Cu].[Zn]>[O:1]=[C:2]1[CH2:3][CH:4]([CH2:5][O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[C:14]1([Cl:15])[Cl:16]\"}",
"reactionStep": {
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"children": [
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"moleculeId": "sa_5e766e07364aa43e02b11ccd",
"parentId": "12544",
"isLeaf": true,
"molecule": {
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"inchikey": "HUGHWHMUUQNACD-UHFFFAOYSA-N",
"smiles": "C=CCOCc1ccccc1"
},
"smiles": "C=CCOCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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{
"id": "12546",
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"moleculeId": "sa_873910628df3b665bfa201b0",
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"molecule": {
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"inchikey": "PVFOMCVHYWHZJE-UHFFFAOYSA-N",
"smiles": "O=C(Cl)C(Cl)(Cl)Cl"
},
"smiles": "O=C(Cl)C(Cl)(Cl)Cl",
"reactionStepId": null,
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}
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},
{
"id": "12547",
"routeId": "sa_47375f170850dbebf4b03c18",
"moleculeId": "sa_5995aff3aeff665a1f3e984d",
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"molecule": {
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"inchikey": "LELOWRISYMNNSU-UHFFFAOYSA-N",
"smiles": "C#N"
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"smiles": "C#N",
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{
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"molecule": {
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"inchikey": "NQRYJNQNLNOLGT-UHFFFAOYSA-N",
"smiles": "C1CCNCC1"
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}
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}
]
}
}