Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCCCC1(OC)CCN(c2ccc(-c3nnc(-c4ccc(C=O)cc4)s3)cc2)CC1
InChiKey
UAEFPGHTWBBOKT-UHFFFAOYSA-N
Route Signature
1201a7909e13dba90317f04291d1c0c099ac620a10457ec2d712cbbcc5a192e3
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_b4d3518721445f5699e9bcca",
"signature": "1201a7909e13dba90317f04291d1c0c099ac620a10457ec2d712cbbcc5a192e3",
"contentHash": "f04f16453cf0b302426d98757733c8c168831aabc34fc37816ba1ae89cf664ef",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_2474bc27e9366b8bd5c2150e",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00962",
"moleculeId": "sa_fbabd99951aae7366ed8d0a4",
"smiles": "CCCCC1(OC)CCN(c2ccc(-c3nnc(-c4ccc(C=O)cc4)s3)cc2)CC1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_fbabd99951aae7366ed8d0a4",
"inchikey": "UAEFPGHTWBBOKT-UHFFFAOYSA-N",
"smiles": "CCCCC1(OC)CCN(c2ccc(-c3nnc(-c4ccc(C=O)cc4)s3)cc2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13952",
"routeId": "sa_b4d3518721445f5699e9bcca",
"moleculeId": "sa_fbabd99951aae7366ed8d0a4",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_fbabd99951aae7366ed8d0a4",
"inchikey": "UAEFPGHTWBBOKT-UHFFFAOYSA-N",
"smiles": "CCCCC1(OC)CCN(c2ccc(-c3nnc(-c4ccc(C=O)cc4)s3)cc2)CC1"
},
"smiles": "CCCCC1(OC)CCN(c2ccc(-c3nnc(-c4ccc(C=O)cc4)s3)cc2)CC1",
"reactionStepId": "sa_2d196492b7a9623791b5cace",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050004014A1;0212;216472\",\"rsmi\":\"[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14](-[c:15]3[n:16][n:17][c:18](-[c:19]4[cH:20][cH:21][c:22]([CH2:23][OH:24])[cH:25][cH:26]4)[s:27]3)[cH:28][cH:29]2)[CH2:30][CH2:31]1>ClC(Cl)Cl>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14](-[c:15]3[n:16][n:17][c:18](-[c:19]4[cH:20][cH:21][c:22]([CH:23]=[O:24])[cH:25][cH:26]4)[s:27]3)[cH:28][cH:29]2)[CH2:30][CH2:31]1\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14](-[c:15]3[n:16][n:17][c:18](-[c:19]4[cH:20][cH:21][c:22]([CH2:23][OH:24])[cH:25][cH:26]4)[s:27]3)[cH:28][cH:29]2)[CH2:30][CH2:31]1>ClC(Cl)Cl>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14](-[c:15]3[n:16][n:17][c:18](-[c:19]4[cH:20][cH:21][c:22]([CH:23]=[O:24])[cH:25][cH:26]4)[s:27]3)[cH:28][cH:29]2)[CH2:30][CH2:31]1\"}",
"reactionStep": {
"id": "sa_2d196492b7a9623791b5cace",
"reactionHash": "a4cb0101f612ad7c07548947150bce14b69c28e025e6d29d5c37f4b9113d890e"
},
"children": [
{
"id": "13953",
"routeId": "sa_b4d3518721445f5699e9bcca",
"moleculeId": "sa_970507a1eb12f6a3623c1f73",
"parentId": "13952",
"isLeaf": false,
"molecule": {
"id": "sa_970507a1eb12f6a3623c1f73",
"inchikey": "JYVFACTZWZEYOG-UHFFFAOYSA-N",
"smiles": "CCCCC1(OC)CCN(c2ccc(-c3nnc(-c4ccc(CO)cc4)s3)cc2)CC1"
},
"smiles": "CCCCC1(OC)CCN(c2ccc(-c3nnc(-c4ccc(CO)cc4)s3)cc2)CC1",
"reactionStepId": "sa_49a69f6ebb55b4b581a2075f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050004014A1;0215;216473\",\"rsmi\":\"CO[C:23]([c:22]1[cH:21][cH:20][c:19](-[c:18]2[n:17][n:16][c:15](-[c:14]3[cH:13][cH:12][c:11]([N:10]4[CH2:9][CH2:8][C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([O:6][CH3:7])[CH2:31][CH2:30]4)[cH:29][cH:28]3)[s:27]2)[cH:26][cH:25]1)=[O:24]>C1CCOC1.CCOC(C)=O.Cl.O.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14](-[c:15]3[n:16][n:17][c:18](-[c:19]4[cH:20][cH:21][c:22]([CH2:23][OH:24])[cH:25][cH:26]4)[s:27]3)[cH:28][cH:29]2)[CH2:30][CH2:31]1\"},\"mapped_reaction_smiles\":\"CO[C:23]([c:22]1[cH:21][cH:20][c:19](-[c:18]2[n:17][n:16][c:15](-[c:14]3[cH:13][cH:12][c:11]([N:10]4[CH2:9][CH2:8][C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([O:6][CH3:7])[CH2:31][CH2:30]4)[cH:29][cH:28]3)[s:27]2)[cH:26][cH:25]1)=[O:24]>C1CCOC1.CCOC(C)=O.Cl.O.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14](-[c:15]3[n:16][n:17][c:18](-[c:19]4[cH:20][cH:21][c:22]([CH2:23][OH:24])[cH:25][cH:26]4)[s:27]3)[cH:28][cH:29]2)[CH2:30][CH2:31]1\"}",
"reactionStep": {
"id": "sa_49a69f6ebb55b4b581a2075f",
"reactionHash": "7535fa68cabf06a728aedd3e7af207936fc1e6b0cecc254142747a814b7bd301"
},
"children": [
{
"id": "13954",
"routeId": "sa_b4d3518721445f5699e9bcca",
"moleculeId": "sa_24a5215cde31fc13e1527982",
"parentId": "13953",
"isLeaf": false,
"molecule": {
"id": "sa_24a5215cde31fc13e1527982",
"inchikey": "ZMRGUMQWRUDIGT-UHFFFAOYSA-N",
"smiles": "CCCCC1(OC)CCN(c2ccc(-c3nnc(-c4ccc(C(=O)OC)cc4)s3)cc2)CC1"
},
"smiles": "CCCCC1(OC)CCN(c2ccc(-c3nnc(-c4ccc(C(=O)OC)cc4)s3)cc2)CC1",
"reactionStepId": "sa_8cd807722fd59b651c2e4926",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050004014A1;0218;216474\",\"rsmi\":\"O=[C:15]([c:14]1[cH:13][cH:12][c:11]([N:10]2[CH2:9][CH2:8][C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([O:6][CH3:7])[CH2:33][CH2:32]2)[cH:31][cH:30]1)[NH:16][NH:17][C:18](=O)[c:19]1[cH:20][cH:21][c:22]([C:23](=[O:24])[O:25][CH3:26])[cH:27][cH:28]1.S=P12SP3(=S)SP(=S)(S1)[S:29]P(=S)(S2)S3>COCCOC.O>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14](-[c:15]3[n:16][n:17][c:18](-[c:19]4[cH:20][cH:21][c:22]([C:23](=[O:24])[O:25][CH3:26])[cH:27][cH:28]4)[s:29]3)[cH:30][cH:31]2)[CH2:32][CH2:33]1\"},\"mapped_reaction_smiles\":\"O=[C:15]([c:14]1[cH:13][cH:12][c:11]([N:10]2[CH2:9][CH2:8][C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([O:6][CH3:7])[CH2:33][CH2:32]2)[cH:31][cH:30]1)[NH:16][NH:17][C:18](=O)[c:19]1[cH:20][cH:21][c:22]([C:23](=[O:24])[O:25][CH3:26])[cH:27][cH:28]1.S=P12SP3(=S)SP(=S)(S1)[S:29]P(=S)(S2)S3>COCCOC.O>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14](-[c:15]3[n:16][n:17][c:18](-[c:19]4[cH:20][cH:21][c:22]([C:23](=[O:24])[O:25][CH3:26])[cH:27][cH:28]4)[s:29]3)[cH:30][cH:31]2)[CH2:32][CH2:33]1\"}",
"reactionStep": {
"id": "sa_8cd807722fd59b651c2e4926",
"reactionHash": "46989adcf16d15acc36338eb26b2ce23c24241a78e89652b523b84a059243c60"
},
"children": [
{
"id": "13955",
"routeId": "sa_b4d3518721445f5699e9bcca",
"moleculeId": "sa_f37ce737bb04a934b8f12822",
"parentId": "13954",
"isLeaf": false,
"molecule": {
"id": "sa_f37ce737bb04a934b8f12822",
"inchikey": "CJDURIRWVQYQBJ-UHFFFAOYSA-N",
"smiles": "CCCCC1(OC)CCN(c2ccc(C(=O)NNC(=O)c3ccc(C(=O)OC)cc3)cc2)CC1"
},
"smiles": "CCCCC1(OC)CCN(c2ccc(C(=O)NNC(=O)c3ccc(C(=O)OC)cc3)cc2)CC1",
"reactionStepId": "sa_4ab38e7bbee13308d6be525e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050004014A1;0221;216475\",\"rsmi\":\"Cl[C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([C:25](=[O:26])[O:27][CH3:28])[cH:29][cH:30]1.[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[NH:17][NH2:18])[cH:31][cH:32]2)[CH2:33][CH2:34]1>C1CCOC1.O.[Na+].O.c1ccncc1>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[NH:17][NH:18][C:19](=[O:20])[c:21]3[cH:22][cH:23][c:24]([C:25](=[O:26])[O:27][CH3:28])[cH:29][cH:30]3)[cH:31][cH:32]2)[CH2:33][CH2:34]1\"},\"mapped_reaction_smiles\":\"Cl[C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([C:25](=[O:26])[O:27][CH3:28])[cH:29][cH:30]1.[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[NH:17][NH2:18])[cH:31][cH:32]2)[CH2:33][CH2:34]1>C1CCOC1.O.[Na+].O.c1ccncc1>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[NH:17][NH:18][C:19](=[O:20])[c:21]3[cH:22][cH:23][c:24]([C:25](=[O:26])[O:27][CH3:28])[cH:29][cH:30]3)[cH:31][cH:32]2)[CH2:33][CH2:34]1\"}",
"reactionStep": {
"id": "sa_4ab38e7bbee13308d6be525e",
"reactionHash": "9441075824c11d8780da0d257902b9c20698712088b7ba8f5b9b93bd7b3b1e2b"
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"children": [
{
"id": "13956",
"routeId": "sa_b4d3518721445f5699e9bcca",
"moleculeId": "sa_9044a3e0cd51d7b20fb17040",
"parentId": "13955",
"isLeaf": true,
"molecule": {
"id": "sa_9044a3e0cd51d7b20fb17040",
"inchikey": "CVXXHXPNTZBZEL-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(C(=O)Cl)cc1"
},
"smiles": "COC(=O)c1ccc(C(=O)Cl)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13957",
"routeId": "sa_b4d3518721445f5699e9bcca",
"moleculeId": "sa_ce00edfeaf70ec6f86fb562a",
"parentId": "13955",
"isLeaf": false,
"molecule": {
"id": "sa_ce00edfeaf70ec6f86fb562a",
"inchikey": "YCTRAHOCLMJXQW-UHFFFAOYSA-N",
"smiles": "CCCCC1(OC)CCN(c2ccc(C(=O)NN)cc2)CC1"
},
"smiles": "CCCCC1(OC)CCN(c2ccc(C(=O)NN)cc2)CC1",
"reactionStepId": "sa_e4c4802cc24f27f2b0664f70",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050004014A1;0224;216476\",\"rsmi\":\"CCO[C:15]([c:14]1[cH:13][cH:12][c:11]([N:10]2[CH2:9][CH2:8][C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([O:6][CH3:7])[CH2:22][CH2:21]2)[cH:20][cH:19]1)=[O:16].[NH2:17][NH2:18]>C1CCOC1.CCO.O>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[NH:17][NH2:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1\"},\"mapped_reaction_smiles\":\"CCO[C:15]([c:14]1[cH:13][cH:12][c:11]([N:10]2[CH2:9][CH2:8][C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([O:6][CH3:7])[CH2:22][CH2:21]2)[cH:20][cH:19]1)=[O:16].[NH2:17][NH2:18]>C1CCOC1.CCO.O>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[NH:17][NH2:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1\"}",
"reactionStep": {
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"reactionHash": "4d093866d0c09db2621f0c94ed1b84de4d199ff90a625fc588e838cb3cbdd2fe"
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"children": [
{
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"moleculeId": "sa_681b90bfe3789a310096845b",
"parentId": "13957",
"isLeaf": true,
"molecule": {
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"inchikey": "OAKJQQAXSVQMHS-UHFFFAOYSA-N",
"smiles": "NN"
},
"smiles": "NN",
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{
"id": "13959",
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"molecule": {
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"inchikey": "WKVDRQUOSSUXQM-UHFFFAOYSA-N",
"smiles": "CCCCC1(OC)CCN(c2ccc(C(=O)OCC)cc2)CC1"
},
"smiles": "CCCCC1(OC)CCN(c2ccc(C(=O)OCC)cc2)CC1",
"reactionStepId": "sa_9332ce4fd64e6dcaaa50f0b6",
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"metadata": "{\"annotations\":{\"ID\":\"US20050004014A1;0227;216477\",\"rsmi\":\"F[c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[cH:20][cH:21]1.[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][NH:10][CH2:22][CH2:23]1>CCOC(C)=O.CS(C)=O.O.O=C(O)C(F)(F)F.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[cH:20][cH:21]2)[CH2:22][CH2:23]1\"},\"mapped_reaction_smiles\":\"F[c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[cH:20][cH:21]1.[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][NH:10][CH2:22][CH2:23]1>CCOC(C)=O.CS(C)=O.O.O=C(O)C(F)(F)F.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([O:6][CH3:7])[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[cH:20][cH:21]2)[CH2:22][CH2:23]1\"}",
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"children": [
{
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"moleculeId": "sa_6e42155063fd2b646a6729b7",
"parentId": "13959",
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"molecule": {
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"inchikey": "MONHCLSLIHTUEA-UHFFFAOYSA-N",
"smiles": "CCCCC1(OC)CCNCC1"
},
"smiles": "CCCCC1(OC)CCNCC1",
"reactionStepId": null,
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"metadata": null,
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},
{
"id": "13961",
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"parentId": "13959",
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"molecule": {
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"inchikey": "UMPRJGKLMUDRHL-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ccc(F)cc1"
},
"smiles": "CCOC(=O)c1ccc(F)cc1",
"reactionStepId": null,
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}
]
}
]
}
]
},
{
"id": "13962",
"routeId": "sa_b4d3518721445f5699e9bcca",
"moleculeId": "sa_e75f66761926d88637d11f4e",
"parentId": "13954",
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"molecule": {
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"inchikey": "CYQAYERJWZKYML-UHFFFAOYSA-N",
"smiles": "S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3"
},
"smiles": "S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3",
"reactionStepId": null,
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}
]
}
]
}
]
}
}