Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
NC(=O)Cc1cccc(-c2nn(C3CCCC3)c3cc[nH]c(=O)c23)c1
InChiKey
QSECHCGJQIOXGP-UHFFFAOYSA-N
Route Signature
550b90c7334e5f7d627ead02d78cf9c56c44437293fa0eb74df426e630f2831a
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_1fe55942b61397d998b41c74",
"signature": "550b90c7334e5f7d627ead02d78cf9c56c44437293fa0eb74df426e630f2831a",
"contentHash": "5c6d1b89bd1945ff98a7ed7a2aa418efc47846aa00b0b53a4ea100b14619fd26",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_5cf1114790eaf1351e5725f1",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00108",
"moleculeId": "sa_bee2f2e064b1c718fe2ae62a",
"smiles": "NC(=O)Cc1cccc(-c2nn(C3CCCC3)c3cc[nH]c(=O)c23)c1",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_bee2f2e064b1c718fe2ae62a",
"inchikey": "QSECHCGJQIOXGP-UHFFFAOYSA-N",
"smiles": "NC(=O)Cc1cccc(-c2nn(C3CCCC3)c3cc[nH]c(=O)c23)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12440",
"routeId": "sa_1fe55942b61397d998b41c74",
"moleculeId": "sa_bee2f2e064b1c718fe2ae62a",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_bee2f2e064b1c718fe2ae62a",
"inchikey": "QSECHCGJQIOXGP-UHFFFAOYSA-N",
"smiles": "NC(=O)Cc1cccc(-c2nn(C3CCCC3)c3cc[nH]c(=O)c23)c1"
},
"smiles": "NC(=O)Cc1cccc(-c2nn(C3CCCC3)c3cc[nH]c(=O)c23)c1",
"reactionStepId": "sa_4a54d25dcf6b4c9ce1b81a4d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251352A1;2089;1928363\",\"rsmi\":\"O[OH:3].[N:1]#[C:2][CH2:4][c:5]1[cH:6][c:7](-[c:8]2[n:9][n:10]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[c:16]3[c:17]2[c:18](=[O:19])[nH:20][cH:21][cH:22]3)[cH:23][cH:24][cH:25]1>CS(C)=O.O.O=C(O)O.[K+].[K+]>[NH2:1][C:2](=[O:3])[CH2:4][c:5]1[cH:6][c:7](-[c:8]2[n:9][n:10]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[c:16]3[c:17]2[c:18](=[O:19])[nH:20][cH:21][cH:22]3)[cH:23][cH:24][cH:25]1\"},\"mapped_reaction_smiles\":\"O[OH:3].[N:1]#[C:2][CH2:4][c:5]1[cH:6][c:7](-[c:8]2[n:9][n:10]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[c:16]3[c:17]2[c:18](=[O:19])[nH:20][cH:21][cH:22]3)[cH:23][cH:24][cH:25]1>CS(C)=O.O.O=C(O)O.[K+].[K+]>[NH2:1][C:2](=[O:3])[CH2:4][c:5]1[cH:6][c:7](-[c:8]2[n:9][n:10]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[c:16]3[c:17]2[c:18](=[O:19])[nH:20][cH:21][cH:22]3)[cH:23][cH:24][cH:25]1\"}",
"reactionStep": {
"id": "sa_4a54d25dcf6b4c9ce1b81a4d",
"reactionHash": "e591fa4cb868a6862a42c18633310c7bc36e6388671f57aac5019f040f115a6c"
},
"children": [
{
"id": "12441",
"routeId": "sa_1fe55942b61397d998b41c74",
"moleculeId": "sa_18d7d6d434a1be835e4f579f",
"parentId": "12440",
"isLeaf": false,
"molecule": {
"id": "sa_18d7d6d434a1be835e4f579f",
"inchikey": "IAKYWRUFSQSFEP-UHFFFAOYSA-N",
"smiles": "N#CCc1cccc(-c2nn(C3CCCC3)c3cc[nH]c(=O)c23)c1"
},
"smiles": "N#CCc1cccc(-c2nn(C3CCCC3)c3cc[nH]c(=O)c23)c1",
"reactionStepId": "sa_6fdf43324e5853b6ee9a7c72",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251352A1;1910;1928335\",\"rsmi\":\"C[O:18][c:17]1[c:16]2[c:7](-[c:6]3[cH:5][c:4]([CH2:3][C:2]#[N:1])[cH:24][cH:23][cH:22]3)[n:8][n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)[c:15]2[cH:21][cH:20][n:19]1>CC#N.C[Si](C)(C)Cl.O.I.[Na+]>[N:1]#[C:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[n:8][n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)[c:15]3[c:16]2[c:17](=[O:18])[nH:19][cH:20][cH:21]3)[cH:22][cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"C[O:18][c:17]1[c:16]2[c:7](-[c:6]3[cH:5][c:4]([CH2:3][C:2]#[N:1])[cH:24][cH:23][cH:22]3)[n:8][n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)[c:15]2[cH:21][cH:20][n:19]1>CC#N.C[Si](C)(C)Cl.O.I.[Na+]>[N:1]#[C:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[n:8][n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)[c:15]3[c:16]2[c:17](=[O:18])[nH:19][cH:20][cH:21]3)[cH:22][cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_6fdf43324e5853b6ee9a7c72",
"reactionHash": "ac526f5aa710292c6e3156464018e3c02a74b6211718b0921a1bf64dd38705a8"
},
"children": [
{
"id": "12442",
"routeId": "sa_1fe55942b61397d998b41c74",
"moleculeId": "sa_fcea02d6c963835fb4658a8c",
"parentId": "12441",
"isLeaf": false,
"molecule": {
"id": "sa_fcea02d6c963835fb4658a8c",
"inchikey": "OXIFMESBGOVDTK-UHFFFAOYSA-N",
"smiles": "COc1nccc2c1c(-c1cccc(CC#N)c1)nn2C1CCCC1"
},
"smiles": "COc1nccc2c1c(-c1cccc(CC#N)c1)nn2C1CCCC1",
"reactionStepId": "sa_3db349becbae20cf6c821bce",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251352A1;1906;1928334\",\"rsmi\":\"CC1(C)OB([c:10]2[cH:11][cH:12][cH:13][c:14]([CH2:15][C:16]#[N:17])[cH:18]2)OC1(C)C.O=S(=O)(O[c:9]1[c:8]2[c:3]([O:2][CH3:1])[n:4][cH:5][cH:6][c:7]2[n:20]([CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[n:19]1)C(F)(F)F>COCCOC.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]2[c:8]1[c:9](-[c:10]1[cH:11][cH:12][cH:13][c:14]([CH2:15][C:16]#[N:17])[cH:18]1)[n:19][n:20]2[CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:10]2[cH:11][cH:12][cH:13][c:14]([CH2:15][C:16]#[N:17])[cH:18]2)OC1(C)C.O=S(=O)(O[c:9]1[c:8]2[c:3]([O:2][CH3:1])[n:4][cH:5][cH:6][c:7]2[n:20]([CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[n:19]1)C(F)(F)F>COCCOC.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]2[c:8]1[c:9](-[c:10]1[cH:11][cH:12][cH:13][c:14]([CH2:15][C:16]#[N:17])[cH:18]1)[n:19][n:20]2[CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25]1\"}",
"reactionStep": {
"id": "sa_3db349becbae20cf6c821bce",
"reactionHash": "94cc85d4ca9f30bfff0ef311cfb3dd428330f4546bcdbd7451e48c17bd3b5c01"
},
"children": [
{
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"routeId": "sa_1fe55942b61397d998b41c74",
"moleculeId": "sa_9605e32bdeb64262cf16eb16",
"parentId": "12442",
"isLeaf": false,
"molecule": {
"id": "sa_9605e32bdeb64262cf16eb16",
"inchikey": "KIPKPQTVNIMEFN-UHFFFAOYSA-N",
"smiles": "COc1nccc2c1c(OS(=O)(=O)C(F)(F)F)nn2C1CCCC1"
},
"smiles": "COc1nccc2c1c(OS(=O)(=O)C(F)(F)F)nn2C1CCCC1",
"reactionStepId": "sa_e6816393415a021692ca1b03",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251352A1;1145;1928178\",\"rsmi\":\"O=S(=O)(O[S:11](=[O:12])(=[O:13])[C:14]([F:15])([F:16])[F:17])C(F)(F)F.[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]2[c:8]1[c:9](=[O:10])[nH:18][n:19]2[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1>CC#N.c1ccncc1>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]2[c:8]1[c:9]([O:10][S:11](=[O:12])(=[O:13])[C:14]([F:15])([F:16])[F:17])[n:18][n:19]2[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1\"},\"mapped_reaction_smiles\":\"O=S(=O)(O[S:11](=[O:12])(=[O:13])[C:14]([F:15])([F:16])[F:17])C(F)(F)F.[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]2[c:8]1[c:9](=[O:10])[nH:18][n:19]2[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1>CC#N.c1ccncc1>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]2[c:8]1[c:9]([O:10][S:11](=[O:12])(=[O:13])[C:14]([F:15])([F:16])[F:17])[n:18][n:19]2[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1\"}",
"reactionStep": {
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"reactionHash": "7f6a5c31c07472dfd700b58a4469ab19abc298fe56775fbbe48e366d957cc902"
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"children": [
{
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"routeId": "sa_1fe55942b61397d998b41c74",
"moleculeId": "sa_a2a1611258dbbb2d21959863",
"parentId": "12443",
"isLeaf": false,
"molecule": {
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"inchikey": "CSONRUCYKYCZFV-UHFFFAOYSA-N",
"smiles": "COc1nccc2c1c(=O)[nH]n2C1CCCC1"
},
"smiles": "COc1nccc2c1c(=O)[nH]n2C1CCCC1",
"reactionStepId": "sa_8ee1a2de2dcd820e265962a1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251352A1;1143;1928177\",\"rsmi\":\"I[c:7]1[cH:6][cH:5][n:4][c:3]([O:2][CH3:1])[c:8]1[C:9](=[O:10])[NH:11][NH:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1>CS(C)=O.O.O=C(O)[C@@H]1CCCN1.O=C(O)O.[Cu]I.[K+].[K+]>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]2[c:8]1[c:9](=[O:10])[nH:11][n:12]2[CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1\"},\"mapped_reaction_smiles\":\"I[c:7]1[cH:6][cH:5][n:4][c:3]([O:2][CH3:1])[c:8]1[C:9](=[O:10])[NH:11][NH:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1>CS(C)=O.O.O=C(O)[C@@H]1CCCN1.O=C(O)O.[Cu]I.[K+].[K+]>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]2[c:8]1[c:9](=[O:10])[nH:11][n:12]2[CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_e13b9f06c59ed722c21fb01c",
"parentId": "12444",
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"molecule": {
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"inchikey": "PHDPBVKLFAFMIO-UHFFFAOYSA-N",
"smiles": "COc1nccc(I)c1C(=O)NNC1CCCC1"
},
"smiles": "COc1nccc(I)c1C(=O)NNC1CCCC1",
"reactionStepId": "sa_bdca4d51e7c74387f02f2caf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251352A1;1141;1928176\",\"rsmi\":\"O[C:5]([c:4]1[c:3]([O:2][CH3:1])[n:18][cH:17][cH:16][c:14]1[I:15])=[O:6].[NH2:7][NH:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1>CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.O.On1nnc2ccccc21>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][NH:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[c:14]([I:15])[cH:16][cH:17][n:18]1\"},\"mapped_reaction_smiles\":\"O[C:5]([c:4]1[c:3]([O:2][CH3:1])[n:18][cH:17][cH:16][c:14]1[I:15])=[O:6].[NH2:7][NH:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1>CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.O.On1nnc2ccccc21>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][NH:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[c:14]([I:15])[cH:16][cH:17][n:18]1\"}",
"reactionStep": {
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"molecule": {
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"inchikey": "NXHFZUVHADJHDW-UHFFFAOYSA-N",
"smiles": "NNC1CCCC1"
},
"smiles": "NNC1CCCC1",
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{
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"smiles": "COc1nccc(I)c1C(=O)O",
"reactionStepId": "sa_71d90ac3e8c37770945b3cce",
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"metadata": "{\"annotations\":{\"ID\":\"US20160251352A1;1075;1928154\",\"rsmi\":\"C[O:7][C:5]([c:4]1[c:3]([O:2][CH3:1])[n:12][cH:11][cH:10][c:8]1[I:9])=[O:6]>CO.[Na+].O>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[OH:7])[c:8]([I:9])[cH:10][cH:11][n:12]1\"},\"mapped_reaction_smiles\":\"C[O:7][C:5]([c:4]1[c:3]([O:2][CH3:1])[n:12][cH:11][cH:10][c:8]1[I:9])=[O:6]>CO.[Na+].O>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[OH:7])[c:8]([I:9])[cH:10][cH:11][n:12]1\"}",
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},
{
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"molecule": {
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"inchikey": "WJKHJLXJJJATHN-UHFFFAOYSA-N",
"smiles": "O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F"
},
"smiles": "O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F",
"reactionStepId": null,
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}
]
},
{
"id": "12450",
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"moleculeId": "sa_2d3c9849823ef7bbe2d670f9",
"parentId": "12442",
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"molecule": {
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"inchikey": "LIWPKYSGWSFPEE-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cccc(CC#N)c2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2cccc(CC#N)c2)OC1(C)C",
"reactionStepId": null,
"template": null,
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}
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}
]
},
{
"id": "12451",
"routeId": "sa_1fe55942b61397d998b41c74",
"moleculeId": "sa_4dba68d938224067da688ab5",
"parentId": "12440",
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"molecule": {
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"inchikey": "MHAJPDPJQMAIIY-UHFFFAOYSA-N",
"smiles": "OO"
},
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"children": []
}
]
}
}