Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(C)CCOc1ccc(-c2cccc(N)n2)c(C2CCCC2)c1
InChiKey
IDYJPRNTQPSUOV-UHFFFAOYSA-N
Route Signature
079e59843eb840bf0e1c6f6174988bcc7398ba095a526a56158976bea4a1f073
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_ad47afc57a9bd7517f30ab05",
"signature": "079e59843eb840bf0e1c6f6174988bcc7398ba095a526a56158976bea4a1f073",
"contentHash": "da365454dc6be581ef57598e9d63a28afd5c85d03a663c00e25976a8907cd648",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_e818358e88ed7c40fb4afb33",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00270",
"moleculeId": "sa_96abd15590a29f5097f69d9b",
"smiles": "CN(C)CCOc1ccc(-c2cccc(N)n2)c(C2CCCC2)c1",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_96abd15590a29f5097f69d9b",
"inchikey": "IDYJPRNTQPSUOV-UHFFFAOYSA-N",
"smiles": "CN(C)CCOc1ccc(-c2cccc(N)n2)c(C2CCCC2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12963",
"routeId": "sa_ad47afc57a9bd7517f30ab05",
"moleculeId": "sa_96abd15590a29f5097f69d9b",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_96abd15590a29f5097f69d9b",
"inchikey": "IDYJPRNTQPSUOV-UHFFFAOYSA-N",
"smiles": "CN(C)CCOc1ccc(-c2cccc(N)n2)c(C2CCCC2)c1"
},
"smiles": "CN(C)CCOc1ccc(-c2cccc(N)n2)c(C2CCCC2)c1",
"reactionStepId": "sa_4190962661921321f8bbf76c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20030162765A1;0242;93119\",\"rsmi\":\"Cl[CH2:5][CH2:4][N:2]([CH3:1])[CH3:3].[OH:6][c:7]1[cH:8][c:9]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][c:20]([NH2:21])[n:22]2)[cH:23][cH:24]1>CC(C)=O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][c:7]1[cH:8][c:9]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][c:20]([NH2:21])[n:22]2)[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:5][CH2:4][N:2]([CH3:1])[CH3:3].[OH:6][c:7]1[cH:8][c:9]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][c:20]([NH2:21])[n:22]2)[cH:23][cH:24]1>CC(C)=O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][c:7]1[cH:8][c:9]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][c:20]([NH2:21])[n:22]2)[cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_4190962661921321f8bbf76c",
"reactionHash": "37302328406a6be60ad1e43e03b5fb05625d6218205248e66e4cad5a48c2b867"
},
"children": [
{
"id": "12964",
"routeId": "sa_ad47afc57a9bd7517f30ab05",
"moleculeId": "sa_708978c2393b6808fce1bd27",
"parentId": "12963",
"isLeaf": false,
"molecule": {
"id": "sa_708978c2393b6808fce1bd27",
"inchikey": "NWBNXZXGFIIUIP-UHFFFAOYSA-N",
"smiles": "Nc1cccc(-c2ccc(O)cc2C2CCCC2)n1"
},
"smiles": "Nc1cccc(-c2ccc(O)cc2C2CCCC2)n1",
"reactionStepId": "sa_dc0747a89d504f50261610cc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20030162765A1;0240;93118\",\"rsmi\":\"Cc1ccc(C)[n:1]1-[c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[c:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13]3)[cH:14][c:15]([OH:16])[cH:17][cH:18]2)[n:19]1>CCO.Cl.NO>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[c:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13]3)[cH:14][c:15]([OH:16])[cH:17][cH:18]2)[n:19]1\"},\"mapped_reaction_smiles\":\"Cc1ccc(C)[n:1]1-[c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[c:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13]3)[cH:14][c:15]([OH:16])[cH:17][cH:18]2)[n:19]1>CCO.Cl.NO>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[c:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13]3)[cH:14][c:15]([OH:16])[cH:17][cH:18]2)[n:19]1\"}",
"reactionStep": {
"id": "sa_dc0747a89d504f50261610cc",
"reactionHash": "be6a8af350760ad429273cb282708da5f81080b0cb1462f561f0fd619afb9fd2"
},
"children": [
{
"id": "12965",
"routeId": "sa_ad47afc57a9bd7517f30ab05",
"moleculeId": "sa_0130d25b3b7d621c7f2befe9",
"parentId": "12964",
"isLeaf": false,
"molecule": {
"id": "sa_0130d25b3b7d621c7f2befe9",
"inchikey": "FLQGPIHEAMUIHC-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C)n1-c1cccc(-c2ccc(O)cc2C2CCCC2)n1"
},
"smiles": "Cc1ccc(C)n1-c1cccc(-c2ccc(O)cc2C2CCCC2)n1",
"reactionStepId": "sa_759390337c7575d7234aab19",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20030162765A1;0237;93117\",\"rsmi\":\"c1ccc(C[O:22][c:21]2[cH:20][c:14]([CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)[c:13](-[c:12]3[cH:11][cH:10][cH:9][c:8](-[n:7]4[c:2]([CH3:1])[cH:3][cH:4][c:5]4[CH3:6])[n:25]3)[cH:24][cH:23]2)cc1>O=CO.N.O.O.[Pd+2]>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[n:7]1-[c:8]1[cH:9][cH:10][cH:11][c:12](-[c:13]2[c:14]([CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)[cH:20][c:21]([OH:22])[cH:23][cH:24]2)[n:25]1\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:22][c:21]2[cH:20][c:14]([CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)[c:13](-[c:12]3[cH:11][cH:10][cH:9][c:8](-[n:7]4[c:2]([CH3:1])[cH:3][cH:4][c:5]4[CH3:6])[n:25]3)[cH:24][cH:23]2)cc1>O=CO.N.O.O.[Pd+2]>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[n:7]1-[c:8]1[cH:9][cH:10][cH:11][c:12](-[c:13]2[c:14]([CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)[cH:20][c:21]([OH:22])[cH:23][cH:24]2)[n:25]1\"}",
"reactionStep": {
"id": "sa_759390337c7575d7234aab19",
"reactionHash": "015194b56e009b89c83e0c01f3e8b649550bbc35a7b84323699518d87a1fc1cc"
},
"children": [
{
"id": "12966",
"routeId": "sa_ad47afc57a9bd7517f30ab05",
"moleculeId": "sa_c9e334a730e45fee30191115",
"parentId": "12965",
"isLeaf": false,
"molecule": {
"id": "sa_c9e334a730e45fee30191115",
"inchikey": "NVDHZNLLVKOCPB-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C)n1-c1cccc(-c2ccc(OCc3ccccc3)cc2C2CCCC2)n1"
},
"smiles": "Cc1ccc(C)n1-c1cccc(-c2ccc(OCc3ccccc3)cc2C2CCCC2)n1",
"reactionStepId": "sa_591d9886f9c35a0978b1f78c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20030162765A1;0234;93116\",\"rsmi\":\"Br[c:12]1[cH:11][cH:10][cH:9][c:8](-[n:7]2[c:2]([CH3:1])[cH:3][cH:4][c:5]2[CH3:6])[n:32]1.OB(O)[c:13]1[c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20][c:21]([O:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[cH:30][cH:31]1>[Pd]>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[n:7]1-[c:8]1[cH:9][cH:10][cH:11][c:12](-[c:13]2[c:14]([CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)[cH:20][c:21]([O:22][CH2:23][c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:30][cH:31]2)[n:32]1\"},\"mapped_reaction_smiles\":\"Br[c:12]1[cH:11][cH:10][cH:9][c:8](-[n:7]2[c:2]([CH3:1])[cH:3][cH:4][c:5]2[CH3:6])[n:32]1.OB(O)[c:13]1[c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20][c:21]([O:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[cH:30][cH:31]1>[Pd]>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[n:7]1-[c:8]1[cH:9][cH:10][cH:11][c:12](-[c:13]2[c:14]([CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)[cH:20][c:21]([O:22][CH2:23][c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:30][cH:31]2)[n:32]1\"}",
"reactionStep": {
"id": "sa_591d9886f9c35a0978b1f78c",
"reactionHash": "eff0e12a88ea47111f1c00736f262960db7cb39e3473e9cd0848ae80021158b0"
},
"children": [
{
"id": "12967",
"routeId": "sa_ad47afc57a9bd7517f30ab05",
"moleculeId": "sa_91c0918cc62c513fdc875fcc",
"parentId": "12966",
"isLeaf": true,
"molecule": {
"id": "sa_91c0918cc62c513fdc875fcc",
"inchikey": "AEKQCMMJOMDJPC-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C)n1-c1cccc(Br)n1"
},
"smiles": "Cc1ccc(C)n1-c1cccc(Br)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12968",
"routeId": "sa_ad47afc57a9bd7517f30ab05",
"moleculeId": "sa_741b93ad56251772f983b170",
"parentId": "12966",
"isLeaf": false,
"molecule": {
"id": "sa_741b93ad56251772f983b170",
"inchikey": "PCQJZQFJTUYDOI-UHFFFAOYSA-N",
"smiles": "OB(O)c1ccc(OCc2ccccc2)cc1C1CCCC1"
},
"smiles": "OB(O)c1ccc(OCc2ccccc2)cc1C1CCCC1",
"reactionStepId": "sa_bd46cd18df39c594a855c7ee",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20030162765A1;0231;93115\",\"rsmi\":\"Br[c:4]1[c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[cH:11][c:12]([O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1.CCO[B:2]([O:1]CC)[O:3]CC>[Li]CCCC>[OH:1][B:2]([OH:3])[c:4]1[c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[cH:11][c:12]([O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"Br[c:4]1[c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[cH:11][c:12]([O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1.CCO[B:2]([O:1]CC)[O:3]CC>[Li]CCCC>[OH:1][B:2]([OH:3])[c:4]1[c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[cH:11][c:12]([O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_bd46cd18df39c594a855c7ee",
"reactionHash": "5d1d331263a340d95ca91fdf81d35742c7613abaad908c1666c71ee4971f5d98"
},
"children": [
{
"id": "12969",
"routeId": "sa_ad47afc57a9bd7517f30ab05",
"moleculeId": "sa_7796e56a8eebba40e0f97628",
"parentId": "12968",
"isLeaf": true,
"molecule": {
"id": "sa_7796e56a8eebba40e0f97628",
"inchikey": "AJSTXXYNEIHPMD-UHFFFAOYSA-N",
"smiles": "CCOB(OCC)OCC"
},
"smiles": "CCOB(OCC)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12970",
"routeId": "sa_ad47afc57a9bd7517f30ab05",
"moleculeId": "sa_51a06aa071adf2cbdca1dfc7",
"parentId": "12968",
"isLeaf": false,
"molecule": {
"id": "sa_51a06aa071adf2cbdca1dfc7",
"inchikey": "DOHBDYZGYOJXOA-UHFFFAOYSA-N",
"smiles": "Brc1ccc(OCc2ccccc2)cc1C1CCCC1"
},
"smiles": "Brc1ccc(OCc2ccccc2)cc1C1CCCC1",
"reactionStepId": "sa_39857d335dd3cee7d2f26422",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20030162765A1;0228;93114\",\"rsmi\":\"O=C1CCC(=O)N1[Br:1].[cH:2]1[c:3]([CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8]2)[cH:9][c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1>>[Br:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8]2)[cH:9][c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:1].[cH:2]1[c:3]([CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8]2)[cH:9][c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1>>[Br:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8]2)[cH:9][c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1\"}",
"reactionStep": {
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"reactionHash": "600ba56547f95e0fc300f46fc2907f308125aa74e8077702bddf1383598f86d5"
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"children": [
{
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"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "12970",
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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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"metadata": null,
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},
{
"id": "12972",
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"molecule": {
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"inchikey": "UWGVYABJZODXCG-UHFFFAOYSA-N",
"smiles": "c1ccc(COc2cccc(C3CCCC3)c2)cc1"
},
"smiles": "c1ccc(COc2cccc(C3CCCC3)c2)cc1",
"reactionStepId": "sa_f8422f85a8fed9c1fb541977",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20030162765A1;0225;93113\",\"rsmi\":\"Br[CH2:5][c:4]1[cH:3][cH:2][cH:1][cH:19][cH:18]1.[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[cH:17]1>CC(C)=O.O=C(O)O.[K+].[K+]>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][cH:10][c:11]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17]2)[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"Br[CH2:5][c:4]1[cH:3][cH:2][cH:1][cH:19][cH:18]1.[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[cH:17]1>CC(C)=O.O=C(O)O.[K+].[K+]>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][cH:10][c:11]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17]2)[cH:18][cH:19]1\"}",
"reactionStep": {
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"reactionHash": "8cfaae306eb59473a34819a55a78ea2d06bd93e9049dd18af31c9220b92bf9b7"
},
"children": [
{
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"routeId": "sa_ad47afc57a9bd7517f30ab05",
"moleculeId": "sa_4ff2e4de9d80150de333c065",
"parentId": "12972",
"isLeaf": true,
"molecule": {
"id": "sa_4ff2e4de9d80150de333c065",
"inchikey": "AGEZXYOZHKGVCM-UHFFFAOYSA-N",
"smiles": "BrCc1ccccc1"
},
"smiles": "BrCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "12974",
"routeId": "sa_ad47afc57a9bd7517f30ab05",
"moleculeId": "sa_af30b13ef3f791cac1005d07",
"parentId": "12972",
"isLeaf": true,
"molecule": {
"id": "sa_af30b13ef3f791cac1005d07",
"inchikey": "NZJMQFDGADIRLV-UHFFFAOYSA-N",
"smiles": "Oc1cccc(C2CCCC2)c1"
},
"smiles": "Oc1cccc(C2CCCC2)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
]
}
]
}
]
},
{
"id": "12975",
"routeId": "sa_ad47afc57a9bd7517f30ab05",
"moleculeId": "sa_2f8d3ee7517e7ddeb1269628",
"parentId": "12963",
"isLeaf": true,
"molecule": {
"id": "sa_2f8d3ee7517e7ddeb1269628",
"inchikey": "WQMAANNAZKNUDL-UHFFFAOYSA-N",
"smiles": "CN(C)CCCl"
},
"smiles": "CN(C)CCCl",
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