Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN1CCC2(CCN(c3cc(C#N)cc(N)c3Cl)CC2)C1=O
InChiKey
XEVSAOFERKTDKW-UHFFFAOYSA-N
Route Signature
10e64b80c80d23032f38981615c37d784382d7e6cdc84da86df37c5b97091128
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_e8131c7469f93e718bbe4820",
"signature": "10e64b80c80d23032f38981615c37d784382d7e6cdc84da86df37c5b97091128",
"contentHash": "ec13f5d5042aa595d083848a05b61093ffd36ba936efc0a09f7f4577a57b7fbb",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_989bd2363e87339dbf86dded",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01175",
"moleculeId": "sa_90230c42868dd321ef101d39",
"smiles": "CN1CCC2(CCN(c3cc(C#N)cc(N)c3Cl)CC2)C1=O",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_90230c42868dd321ef101d39",
"inchikey": "XEVSAOFERKTDKW-UHFFFAOYSA-N",
"smiles": "CN1CCC2(CCN(c3cc(C#N)cc(N)c3Cl)CC2)C1=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10013",
"routeId": "sa_e8131c7469f93e718bbe4820",
"moleculeId": "sa_90230c42868dd321ef101d39",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_90230c42868dd321ef101d39",
"inchikey": "XEVSAOFERKTDKW-UHFFFAOYSA-N",
"smiles": "CN1CCC2(CCN(c3cc(C#N)cc(N)c3Cl)CC2)C1=O"
},
"smiles": "CN1CCC2(CCN(c3cc(C#N)cc(N)c3Cl)CC2)C1=O",
"reactionStepId": "sa_abb619ad6adaadd27b8a6717",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160108050A1;2713;1868356\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:16][c:15]1[cH:14][c:11]([C:12]#[N:13])[cH:10][c:9]([N:8]2[CH2:7][CH2:6][C:5]3([CH2:4][CH2:3][N:2]([CH3:1])[C:21]3=[O:22])[CH2:20][CH2:19]2)[c:17]1[Cl:18]>ClCCl.O=C(O)C(F)(F)F>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][N:8]([c:9]3[cH:10][c:11]([C:12]#[N:13])[cH:14][c:15]([NH2:16])[c:17]3[Cl:18])[CH2:19][CH2:20]2)[C:21]1=[O:22]\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:16][c:15]1[cH:14][c:11]([C:12]#[N:13])[cH:10][c:9]([N:8]2[CH2:7][CH2:6][C:5]3([CH2:4][CH2:3][N:2]([CH3:1])[C:21]3=[O:22])[CH2:20][CH2:19]2)[c:17]1[Cl:18]>ClCCl.O=C(O)C(F)(F)F>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][N:8]([c:9]3[cH:10][c:11]([C:12]#[N:13])[cH:14][c:15]([NH2:16])[c:17]3[Cl:18])[CH2:19][CH2:20]2)[C:21]1=[O:22]\"}",
"reactionStep": {
"id": "sa_abb619ad6adaadd27b8a6717",
"reactionHash": "a428648b6f06e4136b2ef5596c2b56524cc8261212aabe8880a830c235279509"
},
"children": [
{
"id": "10014",
"routeId": "sa_e8131c7469f93e718bbe4820",
"moleculeId": "sa_771ba82aa8e73fada86f0be5",
"parentId": "10013",
"isLeaf": false,
"molecule": {
"id": "sa_771ba82aa8e73fada86f0be5",
"inchikey": "NFBLHWDXUXKRDN-UHFFFAOYSA-N",
"smiles": "CN1CCC2(CCN(c3cc(C#N)cc(NC(=O)OC(C)(C)C)c3Cl)CC2)C1=O"
},
"smiles": "CN1CCC2(CCN(c3cc(C#N)cc(NC(=O)OC(C)(C)C)c3Cl)CC2)C1=O",
"reactionStepId": "sa_3accf41b86eda60ec616a304",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160108050A1;2711;1868355\",\"rsmi\":\"Br[c:9]1[cH:10][c:11]([C:12]#[N:13])[cH:14][c:15]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[c:24]1[Cl:25].[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][NH:8][CH2:26][CH2:27]2)[C:28]1=[O:29]>C1COCCO1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][N:8]([c:9]3[cH:10][c:11]([C:12]#[N:13])[cH:14][c:15]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[c:24]3[Cl:25])[CH2:26][CH2:27]2)[C:28]1=[O:29]\"},\"mapped_reaction_smiles\":\"Br[c:9]1[cH:10][c:11]([C:12]#[N:13])[cH:14][c:15]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[c:24]1[Cl:25].[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][NH:8][CH2:26][CH2:27]2)[C:28]1=[O:29]>C1COCCO1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][N:8]([c:9]3[cH:10][c:11]([C:12]#[N:13])[cH:14][c:15]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[c:24]3[Cl:25])[CH2:26][CH2:27]2)[C:28]1=[O:29]\"}",
"reactionStep": {
"id": "sa_3accf41b86eda60ec616a304",
"reactionHash": "16dcec9007cb07b88215c877fe161198842452090cb0ce44e1da30b2ae53556a"
},
"children": [
{
"id": "10015",
"routeId": "sa_e8131c7469f93e718bbe4820",
"moleculeId": "sa_d1e5f7f786bb912233417308",
"parentId": "10014",
"isLeaf": false,
"molecule": {
"id": "sa_d1e5f7f786bb912233417308",
"inchikey": "JTWGSQNWXVCXLD-UHFFFAOYSA-N",
"smiles": "CN1CCC2(CCNCC2)C1=O"
},
"smiles": "CN1CCC2(CCNCC2)C1=O",
"reactionStepId": "sa_d1d58edea33d47f4ac95cc85",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160108050A1;2709;1868354\",\"rsmi\":\"CC(C)(C)OC(=O)[N:8]1[CH2:7][CH2:6][C:5]2([CH2:4][CH2:3][N:2]([CH3:1])[C:11]2=[O:12])[CH2:10][CH2:9]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)[C:11]1=[O:12]\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:8]1[CH2:7][CH2:6][C:5]2([CH2:4][CH2:3][N:2]([CH3:1])[C:11]2=[O:12])[CH2:10][CH2:9]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)[C:11]1=[O:12]\"}",
"reactionStep": {
"id": "sa_d1d58edea33d47f4ac95cc85",
"reactionHash": "f0c80d8f801ab3904b9017e7ab4dd7413255cb5fa833c6661d8c737a27d6efa2"
},
"children": [
{
"id": "10016",
"routeId": "sa_e8131c7469f93e718bbe4820",
"moleculeId": "sa_b0a2de59faaf5ba5d1ca4e0f",
"parentId": "10015",
"isLeaf": false,
"molecule": {
"id": "sa_b0a2de59faaf5ba5d1ca4e0f",
"inchikey": "MPLXMQMCYBMEIM-UHFFFAOYSA-N",
"smiles": "CN1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O"
},
"smiles": "CN1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O",
"reactionStepId": "sa_4974ac930dbe1846ed87a1bc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160108050A1;2707;1868353\",\"rsmi\":\"I[CH3:1].[NH:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH2:17]2)[C:18]1=[O:19]>C1CCOC1.[HH].[Na+]>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH2:17]2)[C:18]1=[O:19]\"},\"mapped_reaction_smiles\":\"I[CH3:1].[NH:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH2:17]2)[C:18]1=[O:19]>C1CCOC1.[HH].[Na+]>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH2:17]2)[C:18]1=[O:19]\"}",
"reactionStep": {
"id": "sa_4974ac930dbe1846ed87a1bc",
"reactionHash": "f273b3f20ba1182293bf89799f3cf138e84eb4d4178813e012e262f849751556"
},
"children": [
{
"id": "10017",
"routeId": "sa_e8131c7469f93e718bbe4820",
"moleculeId": "sa_651ec4c81afaeb8ab0af1ff0",
"parentId": "10016",
"isLeaf": true,
"molecule": {
"id": "sa_651ec4c81afaeb8ab0af1ff0",
"inchikey": "ADPIEGXXCABJCH-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC2(CCNC2=O)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC2(CCNC2=O)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10018",
"routeId": "sa_e8131c7469f93e718bbe4820",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
"parentId": "10016",
"isLeaf": true,
"molecule": {
"id": "sa_82fdccf7d1cc329c9db73f21",
"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
},
{
"id": "10019",
"routeId": "sa_e8131c7469f93e718bbe4820",
"moleculeId": "sa_ac410a3874a4a29331f183bd",
"parentId": "10014",
"isLeaf": false,
"molecule": {
"id": "sa_ac410a3874a4a29331f183bd",
"inchikey": "LNIYMMILDVTMAL-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)Nc1cc(C#N)cc(Br)c1Cl"
},
"smiles": "CC(C)(C)OC(=O)Nc1cc(C#N)cc(Br)c1Cl",
"reactionStepId": "sa_e7084455c3a10cf1fef62c79",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160108050A1;0483;1867983\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH2:8][c:9]1[c:10]([Cl:11])[c:12]([Br:13])[cH:14][c:15]([C:16]#[N:17])[cH:18]1>CN(C)c1ccncc1.ClCCl.O=C(O)c1ncc[nH]1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[c:10]([Cl:11])[c:12]([Br:13])[cH:14][c:15]([C:16]#[N:17])[cH:18]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH2:8][c:9]1[c:10]([Cl:11])[c:12]([Br:13])[cH:14][c:15]([C:16]#[N:17])[cH:18]1>CN(C)c1ccncc1.ClCCl.O=C(O)c1ncc[nH]1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[c:10]([Cl:11])[c:12]([Br:13])[cH:14][c:15]([C:16]#[N:17])[cH:18]1\"}",
"reactionStep": {
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"reactionHash": "876f9c89df7da8f30892f1710caa9aa3f16fdbc2a4e12079b529d763719a91d9"
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"children": [
{
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"molecule": {
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"inchikey": "BUIBDAUKGIHORD-UHFFFAOYSA-N",
"smiles": "N#Cc1cc(N)c(Cl)c(Br)c1"
},
"smiles": "N#Cc1cc(N)c(Cl)c(Br)c1",
"reactionStepId": "sa_5ce9bb902120a7203d38865b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160108050A1;0483;1867982\",\"rsmi\":\"O=[N+:6]([O-])[c:5]1[cH:4][c:3]([C:2]#[N:1])[cH:11][c:9]([Br:10])[c:7]1[Cl:8]>C1CCOC1.CO.O.Cl.[Fe].N>[N:1]#[C:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([Cl:8])[c:9]([Br:10])[cH:11]1\"},\"mapped_reaction_smiles\":\"O=[N+:6]([O-])[c:5]1[cH:4][c:3]([C:2]#[N:1])[cH:11][c:9]([Br:10])[c:7]1[Cl:8]>C1CCOC1.CO.O.Cl.[Fe].N>[N:1]#[C:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([Cl:8])[c:9]([Br:10])[cH:11]1\"}",
"reactionStep": {
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"children": [
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"moleculeId": "sa_f4c8d97963d71e551d6e2353",
"parentId": "10020",
"isLeaf": true,
"molecule": {
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"inchikey": "DUUZTHQVCWSIRX-UHFFFAOYSA-N",
"smiles": "N#Cc1cc(Br)c(Cl)c([N+](=O)[O-])c1"
},
"smiles": "N#Cc1cc(Br)c(Cl)c([N+](=O)[O-])c1",
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{
"id": "10022",
"routeId": "sa_e8131c7469f93e718bbe4820",
"moleculeId": "sa_b273d4d4546165bca2b249b5",
"parentId": "10019",
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"molecule": {
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"inchikey": "DYHSDKLCOJIUFX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C"
},
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C",
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}
]
}
}