Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN1C(=O)CC(c2ccc(NC(=O)c3nc(C#N)c[nH]3)c(C3=CCCCC3)c2)CC1=O
InChiKey
ZJESLKXOBQREAT-UHFFFAOYSA-N
Route Signature
e434fa61c6be152fedb358270d066d080428061fe2989f5e5625b8ea47dc00c3
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_783b45bdcc909347fd24988e",
"signature": "e434fa61c6be152fedb358270d066d080428061fe2989f5e5625b8ea47dc00c3",
"contentHash": "afa3b07f73c8acf57ccc6ea382cae25b91948df11a3ad51afe0692951e751cb8",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_1d01bc72ebc79768b8d50744",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-04339",
"moleculeId": "sa_753bfe833373e804297079a7",
"smiles": "CN1C(=O)CC(c2ccc(NC(=O)c3nc(C#N)c[nH]3)c(C3=CCCCC3)c2)CC1=O",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_753bfe833373e804297079a7",
"inchikey": "ZJESLKXOBQREAT-UHFFFAOYSA-N",
"smiles": "CN1C(=O)CC(c2ccc(NC(=O)c3nc(C#N)c[nH]3)c(C3=CCCCC3)c2)CC1=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "15451",
"routeId": "sa_783b45bdcc909347fd24988e",
"moleculeId": "sa_753bfe833373e804297079a7",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_753bfe833373e804297079a7",
"inchikey": "ZJESLKXOBQREAT-UHFFFAOYSA-N",
"smiles": "CN1C(=O)CC(c2ccc(NC(=O)c3nc(C#N)c[nH]3)c(C3=CCCCC3)c2)CC1=O"
},
"smiles": "CN1C(=O)CC(c2ccc(NC(=O)c3nc(C#N)c[nH]3)c(C3=CCCCC3)c2)CC1=O",
"reactionStepId": "sa_181c3d8ccd4f968f9197745c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140243382A1;0296;1572165\",\"rsmi\":\"C[Si](C)(C)CCOC[n:26]1[c:20]([C:18]([NH:17][c:16]2[c:9]([C:10]3=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[cH:8][c:7]([CH:6]3[CH2:5][C:3](=[O:4])[N:2]([CH3:1])[C:30](=[O:31])[CH2:29]3)[cH:28][cH:27]2)=[O:19])[n:21][c:22]([C:23]#[N:24])[cH:25]1>CO.ClCCl.O=C(O)C(F)(F)F>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([c:7]2[cH:8][c:9]([C:10]3=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[c:16]([NH:17][C:18](=[O:19])[c:20]3[n:21][c:22]([C:23]#[N:24])[cH:25][nH:26]3)[cH:27][cH:28]2)[CH2:29][C:30]1=[O:31]\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)CCOC[n:26]1[c:20]([C:18]([NH:17][c:16]2[c:9]([C:10]3=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[cH:8][c:7]([CH:6]3[CH2:5][C:3](=[O:4])[N:2]([CH3:1])[C:30](=[O:31])[CH2:29]3)[cH:28][cH:27]2)=[O:19])[n:21][c:22]([C:23]#[N:24])[cH:25]1>CO.ClCCl.O=C(O)C(F)(F)F>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([c:7]2[cH:8][c:9]([C:10]3=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[c:16]([NH:17][C:18](=[O:19])[c:20]3[n:21][c:22]([C:23]#[N:24])[cH:25][nH:26]3)[cH:27][cH:28]2)[CH2:29][C:30]1=[O:31]\"}",
"reactionStep": {
"id": "sa_181c3d8ccd4f968f9197745c",
"reactionHash": "ed14ca61f3f7060f6008ed7b93ffd155c648fc8d2220d6c4545ab2984926a20b"
},
"children": [
{
"id": "15452",
"routeId": "sa_783b45bdcc909347fd24988e",
"moleculeId": "sa_5dffb9c7147e5c684ee86290",
"parentId": "15451",
"isLeaf": false,
"molecule": {
"id": "sa_5dffb9c7147e5c684ee86290",
"inchikey": "IRLYOMTVUXYIIV-UHFFFAOYSA-N",
"smiles": "CN1C(=O)CC(c2ccc(NC(=O)c3nc(C#N)cn3COCC[Si](C)(C)C)c(C3=CCCCC3)c2)CC1=O"
},
"smiles": "CN1C(=O)CC(c2ccc(NC(=O)c3nc(C#N)cn3COCC[Si](C)(C)C)c(C3=CCCCC3)c2)CC1=O",
"reactionStepId": "sa_1545761834b95382ad37b02b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140243382A1;0295;1572164\",\"rsmi\":\"[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([c:7]2[cH:8][c:9]([C:10]3=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[c:16]([NH2:17])[cH:35][cH:36]2)[CH2:37][C:38]1=[O:39].O[C:18](=[O:19])[c:20]1[n:21][c:22]([C:23]#[N:24])[cH:25][n:26]1[CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:33])[CH3:34]>Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.CCN(C(C)C)C(C)C.ClCCl.F[PH](F)(F)(F)(F)F.[K+]>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([c:7]2[cH:8][c:9]([C:10]3=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[c:16]([NH:17][C:18](=[O:19])[c:20]3[n:21][c:22]([C:23]#[N:24])[cH:25][n:26]3[CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:33])[CH3:34])[cH:35][cH:36]2)[CH2:37][C:38]1=[O:39]\"},\"mapped_reaction_smiles\":\"[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([c:7]2[cH:8][c:9]([C:10]3=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[c:16]([NH2:17])[cH:35][cH:36]2)[CH2:37][C:38]1=[O:39].O[C:18](=[O:19])[c:20]1[n:21][c:22]([C:23]#[N:24])[cH:25][n:26]1[CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:33])[CH3:34]>Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.CCN(C(C)C)C(C)C.ClCCl.F[PH](F)(F)(F)(F)F.[K+]>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([c:7]2[cH:8][c:9]([C:10]3=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[c:16]([NH:17][C:18](=[O:19])[c:20]3[n:21][c:22]([C:23]#[N:24])[cH:25][n:26]3[CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:33])[CH3:34])[cH:35][cH:36]2)[CH2:37][C:38]1=[O:39]\"}",
"reactionStep": {
"id": "sa_1545761834b95382ad37b02b",
"reactionHash": "402107bebd0f79eb1a46f8d91d937707dc960786f665236ab473d4a8c07cbf31"
},
"children": [
{
"id": "15453",
"routeId": "sa_783b45bdcc909347fd24988e",
"moleculeId": "sa_121a00529f3880d748fe787f",
"parentId": "15452",
"isLeaf": false,
"molecule": {
"id": "sa_121a00529f3880d748fe787f",
"inchikey": "ASYVLSHERFOFMG-UHFFFAOYSA-N",
"smiles": "CN1C(=O)CC(c2ccc(N)c(C3=CCCCC3)c2)CC1=O"
},
"smiles": "CN1C(=O)CC(c2ccc(N)c(C3=CCCCC3)c2)CC1=O",
"reactionStepId": "sa_503bca446d2c582c11c36771",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140243382A1;0293;1572163\",\"rsmi\":\"Br[c:9]1[cH:8][c:7]([CH:6]2[CH2:5][C:3](=[O:4])[N:2]([CH3:1])[C:21](=[O:22])[CH2:20]2)[cH:19][cH:18][c:16]1[NH2:17].OB(O)[C:10]1=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15]1>C1COCCO1.CC(=O)O.CC(=O)O.CCOC(C)=O.Cc1ccccc1.O=P(O)(O)O.[K+].[K+].[K+].[Pd+2].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([c:7]2[cH:8][c:9]([C:10]3=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[c:16]([NH2:17])[cH:18][cH:19]2)[CH2:20][C:21]1=[O:22]\"},\"mapped_reaction_smiles\":\"Br[c:9]1[cH:8][c:7]([CH:6]2[CH2:5][C:3](=[O:4])[N:2]([CH3:1])[C:21](=[O:22])[CH2:20]2)[cH:19][cH:18][c:16]1[NH2:17].OB(O)[C:10]1=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15]1>C1COCCO1.CC(=O)O.CC(=O)O.CCOC(C)=O.Cc1ccccc1.O=P(O)(O)O.[K+].[K+].[K+].[Pd+2].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([c:7]2[cH:8][c:9]([C:10]3=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[c:16]([NH2:17])[cH:18][cH:19]2)[CH2:20][C:21]1=[O:22]\"}",
"reactionStep": {
"id": "sa_503bca446d2c582c11c36771",
"reactionHash": "33d3a637ebe6cf23ea6fc149cc476400304dc9a3b2c904f50069b2b509e9e818"
},
"children": [
{
"id": "15454",
"routeId": "sa_783b45bdcc909347fd24988e",
"moleculeId": "sa_50aae3c1f94cc2b7ab485a0a",
"parentId": "15453",
"isLeaf": false,
"molecule": {
"id": "sa_50aae3c1f94cc2b7ab485a0a",
"inchikey": "RBDOGCCROYAPSW-UHFFFAOYSA-N",
"smiles": "CN1C(=O)CC(c2ccc(N)c(Br)c2)CC1=O"
},
"smiles": "CN1C(=O)CC(c2ccc(N)c(Br)c2)CC1=O",
"reactionStepId": "sa_5bc1b744fb92ec00e6f4c46a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140243382A1;0291;1572162\",\"rsmi\":\"O=C1CCC(=O)N1[Br:10].[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([c:7]2[cH:8][cH:9][c:11]([NH2:12])[cH:13][cH:14]2)[CH2:15][C:16]1=[O:17]>ClCCl>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([c:7]2[cH:8][c:9]([Br:10])[c:11]([NH2:12])[cH:13][cH:14]2)[CH2:15][C:16]1=[O:17]\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:10].[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([c:7]2[cH:8][cH:9][c:11]([NH2:12])[cH:13][cH:14]2)[CH2:15][C:16]1=[O:17]>ClCCl>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([c:7]2[cH:8][c:9]([Br:10])[c:11]([NH2:12])[cH:13][cH:14]2)[CH2:15][C:16]1=[O:17]\"}",
"reactionStep": {
"id": "sa_5bc1b744fb92ec00e6f4c46a",
"reactionHash": "76e97630a18deafd391924826637a08480cf785421cffa599f41a1886ac71450"
},
"children": [
{
"id": "15455",
"routeId": "sa_783b45bdcc909347fd24988e",
"moleculeId": "sa_44495e275bf4c38831d9a753",
"parentId": "15454",
"isLeaf": false,
"molecule": {
"id": "sa_44495e275bf4c38831d9a753",
"inchikey": "JMDARQRWWCHOPR-UHFFFAOYSA-N",
"smiles": "CN1C(=O)CC(c2ccc(N)cc2)CC1=O"
},
"smiles": "CN1C(=O)CC(c2ccc(N)cc2)CC1=O",
"reactionStepId": "sa_cffcd5246c7de22d4535e477",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140243382A1;0289;1572161\",\"rsmi\":\"O=[N+:11]([O-])[c:10]1[cH:9][cH:8][c:7]([CH:6]2[CH2:5][C:3](=[O:4])[N:2]([CH3:1])[C:15](=[O:16])[CH2:14]2)[cH:13][cH:12]1>CO.[Pd]>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:12][cH:13]2)[CH2:14][C:15]1=[O:16]\"},\"mapped_reaction_smiles\":\"O=[N+:11]([O-])[c:10]1[cH:9][cH:8][c:7]([CH:6]2[CH2:5][C:3](=[O:4])[N:2]([CH3:1])[C:15](=[O:16])[CH2:14]2)[cH:13][cH:12]1>CO.[Pd]>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:12][cH:13]2)[CH2:14][C:15]1=[O:16]\"}",
"reactionStep": {
"id": "sa_cffcd5246c7de22d4535e477",
"reactionHash": "f478c0a2c8ea567b7a668e0966929e737955d2e08421747698c616b124397995"
},
"children": [
{
"id": "15456",
"routeId": "sa_783b45bdcc909347fd24988e",
"moleculeId": "sa_3f0d66f816fe2c7146b39cee",
"parentId": "15455",
"isLeaf": true,
"molecule": {
"id": "sa_3f0d66f816fe2c7146b39cee",
"inchikey": "WWOQSQKGPCFMNO-UHFFFAOYSA-N",
"smiles": "CN1C(=O)CC(c2ccc([N+](=O)[O-])cc2)CC1=O"
},
"smiles": "CN1C(=O)CC(c2ccc([N+](=O)[O-])cc2)CC1=O",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "15457",
"routeId": "sa_783b45bdcc909347fd24988e",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "15454",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "15458",
"routeId": "sa_783b45bdcc909347fd24988e",
"moleculeId": "sa_5467497cb6d60f566dbfb661",
"parentId": "15453",
"isLeaf": true,
"molecule": {
"id": "sa_5467497cb6d60f566dbfb661",
"inchikey": "XZWQKJXJNKYMAP-UHFFFAOYSA-N",
"smiles": "OB(O)C1=CCCCC1"
},
"smiles": "OB(O)C1=CCCCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "15459",
"routeId": "sa_783b45bdcc909347fd24988e",
"moleculeId": "sa_4cbcb4cf2d562e6bf7a55aee",
"parentId": "15452",
"isLeaf": true,
"molecule": {
"id": "sa_4cbcb4cf2d562e6bf7a55aee",
"inchikey": "SQMINWFWFXVWHK-UHFFFAOYSA-N",
"smiles": "C[Si](C)(C)CCOCn1cc(C#N)nc1C(=O)O"
},
"smiles": "C[Si](C)(C)CCOCn1cc(C#N)nc1C(=O)O",
"reactionStepId": null,
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"metadata": null,
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}
]
}
]
}
}