Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCC(C)c1c(O)ccc2c1oc1ccc(C#N)cc12
InChiKey
OVFYOQIDCXLDII-UHFFFAOYSA-N
Route Signature
1ce314242867ce63a619ba2943a0612c68ae03145794fcb2f0a1fb55900e6226
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_7f39be091339c80454e99717",
"signature": "1ce314242867ce63a619ba2943a0612c68ae03145794fcb2f0a1fb55900e6226",
"contentHash": "9f8afe78e9e90ce4e3bcd24db5068dcf5ce5f9e202d031941ca96158aed7cb33",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_0670497eca1377a34f8e2a08",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00402",
"moleculeId": "sa_7147f2a5778b0fe3ed0f9cd7",
"smiles": "CCC(C)c1c(O)ccc2c1oc1ccc(C#N)cc12",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_7147f2a5778b0fe3ed0f9cd7",
"inchikey": "OVFYOQIDCXLDII-UHFFFAOYSA-N",
"smiles": "CCC(C)c1c(O)ccc2c1oc1ccc(C#N)cc12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13203",
"routeId": "sa_7f39be091339c80454e99717",
"moleculeId": "sa_7147f2a5778b0fe3ed0f9cd7",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7147f2a5778b0fe3ed0f9cd7",
"inchikey": "OVFYOQIDCXLDII-UHFFFAOYSA-N",
"smiles": "CCC(C)c1c(O)ccc2c1oc1ccc(C#N)cc12"
},
"smiles": "CCC(C)c1c(O)ccc2c1oc1ccc(C#N)cc12",
"reactionStepId": "sa_132f008fbbffdea3c12f81c6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070093548A1;0121;451100\",\"rsmi\":\"C[O:7][c:6]1[c:5]([CH:3]([CH2:2][CH3:1])[CH3:4])[c:11]2[c:10]([cH:9][cH:8]1)[c:14]1[c:13]([o:12]2)[cH:20][cH:19][c:16]([C:17]#[N:18])[cH:15]1>BrB(Br)Br.ClCCl.O>[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([OH:7])[cH:8][cH:9][c:10]2[c:11]1[o:12][c:13]1[c:14]2[cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"C[O:7][c:6]1[c:5]([CH:3]([CH2:2][CH3:1])[CH3:4])[c:11]2[c:10]([cH:9][cH:8]1)[c:14]1[c:13]([o:12]2)[cH:20][cH:19][c:16]([C:17]#[N:18])[cH:15]1>BrB(Br)Br.ClCCl.O>[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([OH:7])[cH:8][cH:9][c:10]2[c:11]1[o:12][c:13]1[c:14]2[cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_132f008fbbffdea3c12f81c6",
"reactionHash": "f84b71d278c699ebdb55239ba999ae13e2794fd028eed0df65c42238d1e0f3ac"
},
"children": [
{
"id": "13204",
"routeId": "sa_7f39be091339c80454e99717",
"moleculeId": "sa_cd3247e6cc6fe27c478f7569",
"parentId": "13203",
"isLeaf": false,
"molecule": {
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"inchikey": "FNARJIGZZSUAOO-UHFFFAOYSA-N",
"smiles": "CCC(C)c1c(OC)ccc2c1oc1ccc(C#N)cc12"
},
"smiles": "CCC(C)c1c(OC)ccc2c1oc1ccc(C#N)cc12",
"reactionStepId": "sa_cebd9ec047e740c8f10960e4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070093548A1;0119;451099\",\"rsmi\":\"Br[c:11]1[cH:10][cH:9][c:6]([O:7][CH3:8])[c:5]([CH:3]([CH2:2][CH3:1])[CH3:4])[c:12]1[O:13][c:14]1[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]1>CC(=O)N(C)C.CC(=O)O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Na+]>[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([O:7][CH3:8])[cH:9][cH:10][c:11]2[c:12]1[o:13][c:14]1[c:15]2[cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"Br[c:11]1[cH:10][cH:9][c:6]([O:7][CH3:8])[c:5]([CH:3]([CH2:2][CH3:1])[CH3:4])[c:12]1[O:13][c:14]1[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]1>CC(=O)N(C)C.CC(=O)O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Na+]>[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([O:7][CH3:8])[cH:9][cH:10][c:11]2[c:12]1[o:13][c:14]1[c:15]2[cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_cebd9ec047e740c8f10960e4",
"reactionHash": "b80ca48fa467a5d3b01816cc7f389209686cc29bce402a6729c8622fb83d424f"
},
"children": [
{
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"routeId": "sa_7f39be091339c80454e99717",
"moleculeId": "sa_9f9850ea4987955bfb97c4ee",
"parentId": "13204",
"isLeaf": false,
"molecule": {
"id": "sa_9f9850ea4987955bfb97c4ee",
"inchikey": "KSKSETPARFPOBO-UHFFFAOYSA-N",
"smiles": "CCC(C)c1c(OC)ccc(Br)c1Oc1ccc(C#N)cc1"
},
"smiles": "CCC(C)c1c(OC)ccc(Br)c1Oc1ccc(C#N)cc1",
"reactionStepId": "sa_50a375c5b82c2a6295b3bef5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070093548A1;0118;451098\",\"rsmi\":\"O=C1CCC(=O)N1[Br:17].[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]2)[cH:16][cH:18][cH:19][c:20]1[O:21][CH3:22]>CC#N.O=[Si](O)O.[Mg+2]>[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]2)[c:16]([Br:17])[cH:18][cH:19][c:20]1[O:21][CH3:22]\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:17].[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]2)[cH:16][cH:18][cH:19][c:20]1[O:21][CH3:22]>CC#N.O=[Si](O)O.[Mg+2]>[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]2)[c:16]([Br:17])[cH:18][cH:19][c:20]1[O:21][CH3:22]\"}",
"reactionStep": {
"id": "sa_50a375c5b82c2a6295b3bef5",
"reactionHash": "e9b6268b2584fffa5c08e591e5f36645697c82c7d726ce0dae8162dcf6e9078a"
},
"children": [
{
"id": "13206",
"routeId": "sa_7f39be091339c80454e99717",
"moleculeId": "sa_4f90c2b0d7d97f69cfca217a",
"parentId": "13205",
"isLeaf": false,
"molecule": {
"id": "sa_4f90c2b0d7d97f69cfca217a",
"inchikey": "JIGKOPKRNMCFTA-UHFFFAOYSA-N",
"smiles": "CCC(C)c1c(OC)cccc1Oc1ccc(C#N)cc1"
},
"smiles": "CCC(C)c1c(OC)cccc1Oc1ccc(C#N)cc1",
"reactionStepId": "sa_0548dcb1a783be9213b98a9e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070093548A1;0117;451097\",\"rsmi\":\"F[c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1.[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([OH:7])[cH:16][cH:17][cH:18][c:19]1[O:20][CH3:21]>>[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]2)[cH:16][cH:17][cH:18][c:19]1[O:20][CH3:21]\"},\"mapped_reaction_smiles\":\"F[c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1.[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([OH:7])[cH:16][cH:17][cH:18][c:19]1[O:20][CH3:21]>>[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]2)[cH:16][cH:17][cH:18][c:19]1[O:20][CH3:21]\"}",
"reactionStep": {
"id": "sa_0548dcb1a783be9213b98a9e",
"reactionHash": "12aed832e8898e225a1c316a1ea4cec02a09fd463b528e3024754cf2e7fd6871"
},
"children": [
{
"id": "13207",
"routeId": "sa_7f39be091339c80454e99717",
"moleculeId": "sa_0f160c25f1d741c1db2920b6",
"parentId": "13206",
"isLeaf": true,
"molecule": {
"id": "sa_0f160c25f1d741c1db2920b6",
"inchikey": "AEKVBBNGWBBYLL-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(F)cc1"
},
"smiles": "N#Cc1ccc(F)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13208",
"routeId": "sa_7f39be091339c80454e99717",
"moleculeId": "sa_f27064ef433f76f5e78d999e",
"parentId": "13206",
"isLeaf": false,
"molecule": {
"id": "sa_f27064ef433f76f5e78d999e",
"inchikey": "MHCLUKMZMICAPJ-UHFFFAOYSA-N",
"smiles": "CCC(C)c1c(O)cccc1OC"
},
"smiles": "CCC(C)c1c(O)cccc1OC",
"reactionStepId": "sa_f7171378c4a154902b5ed42f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070093548A1;0116;451096\",\"rsmi\":\"C[O:7][c:6]1[c:5]([CH:3]([CH2:2][CH3:1])[CH3:4])[c:11]([O:12][CH3:13])[cH:10][cH:9][cH:8]1>BrB(Br)Br.ClCCl>[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([OH:7])[cH:8][cH:9][cH:10][c:11]1[O:12][CH3:13]\"},\"mapped_reaction_smiles\":\"C[O:7][c:6]1[c:5]([CH:3]([CH2:2][CH3:1])[CH3:4])[c:11]([O:12][CH3:13])[cH:10][cH:9][cH:8]1>BrB(Br)Br.ClCCl>[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([OH:7])[cH:8][cH:9][cH:10][c:11]1[O:12][CH3:13]\"}",
"reactionStep": {
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"reactionHash": "cf69485a8535cc4cce7c04a14f3f3c5afb043cc6feb46109db7168cc58f8f3dd"
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"children": [
{
"id": "13209",
"routeId": "sa_7f39be091339c80454e99717",
"moleculeId": "sa_85c9c9d138698246d4a438ff",
"parentId": "13208",
"isLeaf": false,
"molecule": {
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"inchikey": "HPNZDGHYUDDJOA-UHFFFAOYSA-N",
"smiles": "CCC(C)c1c(OC)cccc1OC"
},
"smiles": "CCC(C)c1c(OC)cccc1OC",
"reactionStepId": "sa_4875130bd9b66a5d420a1c43",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070093548A1;0115;451095\",\"rsmi\":\"O[C:3]([CH2:2][CH3:1])([CH3:4])[c:5]1[c:6]([O:7][CH3:8])[cH:9][cH:10][cH:11][c:12]1[O:13][CH3:14]>CCCCCC.Cc1ccc(S(=O)(=O)O)cc1.O.c1ccccc1>[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([O:7][CH3:8])[cH:9][cH:10][cH:11][c:12]1[O:13][CH3:14]\"},\"mapped_reaction_smiles\":\"O[C:3]([CH2:2][CH3:1])([CH3:4])[c:5]1[c:6]([O:7][CH3:8])[cH:9][cH:10][cH:11][c:12]1[O:13][CH3:14]>CCCCCC.Cc1ccc(S(=O)(=O)O)cc1.O.c1ccccc1>[CH3:1][CH2:2][CH:3]([CH3:4])[c:5]1[c:6]([O:7][CH3:8])[cH:9][cH:10][cH:11][c:12]1[O:13][CH3:14]\"}",
"reactionStep": {
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"reactionHash": "38d81539c5ea6e6d652e9f4676c7e810f7697a83dd509d90474d73cfe24cb898"
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"children": [
{
"id": "13210",
"routeId": "sa_7f39be091339c80454e99717",
"moleculeId": "sa_24f5c8478de9ee1cab54cc24",
"parentId": "13209",
"isLeaf": false,
"molecule": {
"id": "sa_24f5c8478de9ee1cab54cc24",
"inchikey": "HEXPRNLZWQNSDZ-UHFFFAOYSA-N",
"smiles": "CCC(C)(O)c1c(OC)cccc1OC"
},
"smiles": "CCC(C)(O)c1c(OC)cccc1OC",
"reactionStepId": "sa_3d0e2a46f204314d6097c2ab",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070093548A1;0114;451094\",\"rsmi\":\"[CH3:1][CH2:2][C:3]([CH3:4])=[O:5].[cH:6]1[c:7]([O:8][CH3:9])[cH:10][cH:11][cH:12][c:13]1[O:14][CH3:15]>CCOCC.[Li]CCCC>[CH3:1][CH2:2][C:3]([CH3:4])([OH:5])[c:6]1[c:7]([O:8][CH3:9])[cH:10][cH:11][cH:12][c:13]1[O:14][CH3:15]\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][C:3]([CH3:4])=[O:5].[cH:6]1[c:7]([O:8][CH3:9])[cH:10][cH:11][cH:12][c:13]1[O:14][CH3:15]>CCOCC.[Li]CCCC>[CH3:1][CH2:2][C:3]([CH3:4])([OH:5])[c:6]1[c:7]([O:8][CH3:9])[cH:10][cH:11][cH:12][c:13]1[O:14][CH3:15]\"}",
"reactionStep": {
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"reactionHash": "7cd4ef8aba6439cfa7337e71d473b4de0ff0011124488a552ba30963bad57d0d"
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"children": [
{
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"routeId": "sa_7f39be091339c80454e99717",
"moleculeId": "sa_3dfebf4e21f0b9ae71e54d4b",
"parentId": "13210",
"isLeaf": true,
"molecule": {
"id": "sa_3dfebf4e21f0b9ae71e54d4b",
"inchikey": "DPZNOMCNRMUKPS-UHFFFAOYSA-N",
"smiles": "COc1cccc(OC)c1"
},
"smiles": "COc1cccc(OC)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "13212",
"routeId": "sa_7f39be091339c80454e99717",
"moleculeId": "sa_e1d6f22027a20e5fd18e3da2",
"parentId": "13210",
"isLeaf": true,
"molecule": {
"id": "sa_e1d6f22027a20e5fd18e3da2",
"inchikey": "ZWEHNKRNPOVVGH-UHFFFAOYSA-N",
"smiles": "CCC(C)=O"
},
"smiles": "CCC(C)=O",
"reactionStepId": null,
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"metadata": null,
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"children": []
}
]
}
]
}
]
}
]
},
{
"id": "13213",
"routeId": "sa_7f39be091339c80454e99717",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "13205",
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"molecule": {
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"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
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}
]
}
]
}
]
}
}