Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1ncc(C)c(-c2ccc3c(c2)[nH]c(=O)c2cnn([C@H]4CCOC4)c23)c1C
InChiKey
CKJDCNZBABIEBZ-HNNXBMFYSA-N
Route Signature
64ae2afd9c60bd9fac31c538bdf9b78652035a83e420507a91bc1640a99612b3
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_0e5644d021663a192fc9dc9e",
"signature": "64ae2afd9c60bd9fac31c538bdf9b78652035a83e420507a91bc1640a99612b3",
"contentHash": "db025ede1882629ad39b80b292bfa5bf39ac4bcf03e6e4642aa33dfc48904401",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_6193b807c8cd464db4cfb823",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00112",
"moleculeId": "sa_c86c8246c65d93d80607afcc",
"smiles": "COc1ncc(C)c(-c2ccc3c(c2)[nH]c(=O)c2cnn([C@H]4CCOC4)c23)c1C",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_c86c8246c65d93d80607afcc",
"inchikey": "CKJDCNZBABIEBZ-HNNXBMFYSA-N",
"smiles": "COc1ncc(C)c(-c2ccc3c(c2)[nH]c(=O)c2cnn([C@H]4CCOC4)c23)c1C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9183",
"routeId": "sa_0e5644d021663a192fc9dc9e",
"moleculeId": "sa_c86c8246c65d93d80607afcc",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c86c8246c65d93d80607afcc",
"inchikey": "CKJDCNZBABIEBZ-HNNXBMFYSA-N",
"smiles": "COc1ncc(C)c(-c2ccc3c(c2)[nH]c(=O)c2cnn([C@H]4CCOC4)c23)c1C"
},
"smiles": "COc1ncc(C)c(-c2ccc3c(c2)[nH]c(=O)c2cnn([C@H]4CCOC4)c23)c1C",
"reactionStepId": "sa_ef0006f9f4750ec1b3ad54d7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160046623A1;0192;1839182\",\"rsmi\":\"F[c:11]1[cH:10][c:9](-[c:8]2[c:6]([CH3:7])[cH:5][n:4][c:3]([O:2][CH3:1])[c:28]2[CH3:29])[cH:14][cH:13][c:12]1-[c:15]1[c:16]([C:25](=[O:26])[NH2:27])[cH:17][n:18][n:19]1[C@H:20]1[CH2:21][CH2:22][O:23][CH2:24]1>CC(=O)O.CS(C)=O.O.[Na+].O>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[c:12]([cH:13][cH:14]2)[c:15]2[c:16]([cH:17][n:18][n:19]2[C@H:20]2[CH2:21][CH2:22][O:23][CH2:24]2)[c:25](=[O:26])[nH:27]3)[c:28]1[CH3:29]\"},\"mapped_reaction_smiles\":\"F[c:11]1[cH:10][c:9](-[c:8]2[c:6]([CH3:7])[cH:5][n:4][c:3]([O:2][CH3:1])[c:28]2[CH3:29])[cH:14][cH:13][c:12]1-[c:15]1[c:16]([C:25](=[O:26])[NH2:27])[cH:17][n:18][n:19]1[C@H:20]1[CH2:21][CH2:22][O:23][CH2:24]1>CC(=O)O.CS(C)=O.O.[Na+].O>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[c:12]([cH:13][cH:14]2)[c:15]2[c:16]([cH:17][n:18][n:19]2[C@H:20]2[CH2:21][CH2:22][O:23][CH2:24]2)[c:25](=[O:26])[nH:27]3)[c:28]1[CH3:29]\"}",
"reactionStep": {
"id": "sa_ef0006f9f4750ec1b3ad54d7",
"reactionHash": "09fd7ddd0d8b3aa30e68bc1e786469c60bd0948bb39409a6bfbd0593e76117fa"
},
"children": [
{
"id": "9184",
"routeId": "sa_0e5644d021663a192fc9dc9e",
"moleculeId": "sa_e974c41bc73bea156c3a5273",
"parentId": "9183",
"isLeaf": false,
"molecule": {
"id": "sa_e974c41bc73bea156c3a5273",
"inchikey": "LUZGKPIPGYEZON-HNNXBMFYSA-N",
"smiles": "COc1ncc(C)c(-c2ccc(-c3c(C(N)=O)cnn3[C@H]3CCOC3)c(F)c2)c1C"
},
"smiles": "COc1ncc(C)c(-c2ccc(-c3c(C(N)=O)cnn3[C@H]3CCOC3)c(F)c2)c1C",
"reactionStepId": "sa_b44cd0639bdacfb6285d9b66",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160046623A1;0189;1839181\",\"rsmi\":\"O[C:16]([c:15]1[c:14](-[c:13]2[c:11]([F:12])[cH:10][c:9](-[c:8]3[c:6]([CH3:7])[cH:5][n:4][c:3]([O:2][CH3:1])[c:29]3[CH3:30])[cH:28][cH:27]2)[n:21]([C@H:22]2[CH2:23][CH2:24][O:25][CH2:26]2)[n:20][cH:19]1)=[O:18].[NH3:17]>CN(C)C=O.O=C(n1ccnc1)n1ccnc1>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[c:8](-[c:9]2[cH:10][c:11]([F:12])[c:13](-[c:14]3[c:15]([C:16]([NH2:17])=[O:18])[cH:19][n:20][n:21]3[C@H:22]3[CH2:23][CH2:24][O:25][CH2:26]3)[cH:27][cH:28]2)[c:29]1[CH3:30]\"},\"mapped_reaction_smiles\":\"O[C:16]([c:15]1[c:14](-[c:13]2[c:11]([F:12])[cH:10][c:9](-[c:8]3[c:6]([CH3:7])[cH:5][n:4][c:3]([O:2][CH3:1])[c:29]3[CH3:30])[cH:28][cH:27]2)[n:21]([C@H:22]2[CH2:23][CH2:24][O:25][CH2:26]2)[n:20][cH:19]1)=[O:18].[NH3:17]>CN(C)C=O.O=C(n1ccnc1)n1ccnc1>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[c:8](-[c:9]2[cH:10][c:11]([F:12])[c:13](-[c:14]3[c:15]([C:16]([NH2:17])=[O:18])[cH:19][n:20][n:21]3[C@H:22]3[CH2:23][CH2:24][O:25][CH2:26]3)[cH:27][cH:28]2)[c:29]1[CH3:30]\"}",
"reactionStep": {
"id": "sa_b44cd0639bdacfb6285d9b66",
"reactionHash": "515740fbb82edc5185d05041e48d13722ce2f42544a888452185edc57f35bdce"
},
"children": [
{
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"routeId": "sa_0e5644d021663a192fc9dc9e",
"moleculeId": "sa_a2d201f9a19383d8edac7ffa",
"parentId": "9184",
"isLeaf": false,
"molecule": {
"id": "sa_a2d201f9a19383d8edac7ffa",
"inchikey": "PQKGWYVBIOJGNY-HNNXBMFYSA-N",
"smiles": "COc1ncc(C)c(-c2ccc(-c3c(C(=O)O)cnn3[C@H]3CCOC3)c(F)c2)c1C"
},
"smiles": "COc1ncc(C)c(-c2ccc(-c3c(C(=O)O)cnn3[C@H]3CCOC3)c(F)c2)c1C",
"reactionStepId": "sa_bc2554d2d26e01031d69fdac",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160046623A1;0186;1839180\",\"rsmi\":\"CC[O:18][C:16]([c:15]1[c:14](-[c:13]2[c:11]([F:12])[cH:10][c:9](-[c:8]3[c:6]([CH3:7])[cH:5][n:4][c:3]([O:2][CH3:1])[c:29]3[CH3:30])[cH:28][cH:27]2)[n:21]([C@H:22]2[CH2:23][CH2:24][O:25][CH2:26]2)[n:20][cH:19]1)=[O:17]>CCO.[Na+].O>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[c:8](-[c:9]2[cH:10][c:11]([F:12])[c:13](-[c:14]3[c:15]([C:16](=[O:17])[OH:18])[cH:19][n:20][n:21]3[C@H:22]3[CH2:23][CH2:24][O:25][CH2:26]3)[cH:27][cH:28]2)[c:29]1[CH3:30]\"},\"mapped_reaction_smiles\":\"CC[O:18][C:16]([c:15]1[c:14](-[c:13]2[c:11]([F:12])[cH:10][c:9](-[c:8]3[c:6]([CH3:7])[cH:5][n:4][c:3]([O:2][CH3:1])[c:29]3[CH3:30])[cH:28][cH:27]2)[n:21]([C@H:22]2[CH2:23][CH2:24][O:25][CH2:26]2)[n:20][cH:19]1)=[O:17]>CCO.[Na+].O>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[c:8](-[c:9]2[cH:10][c:11]([F:12])[c:13](-[c:14]3[c:15]([C:16](=[O:17])[OH:18])[cH:19][n:20][n:21]3[C@H:22]3[CH2:23][CH2:24][O:25][CH2:26]3)[cH:27][cH:28]2)[c:29]1[CH3:30]\"}",
"reactionStep": {
"id": "sa_bc2554d2d26e01031d69fdac",
"reactionHash": "a2ce0a61767f2bf191df70ff481992fcc715ca1636d6df1dc6c847dc7edbaa37"
},
"children": [
{
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"routeId": "sa_0e5644d021663a192fc9dc9e",
"moleculeId": "sa_1c7c3a643a183d2d1eff761c",
"parentId": "9185",
"isLeaf": false,
"molecule": {
"id": "sa_1c7c3a643a183d2d1eff761c",
"inchikey": "SNYSQNUSZOTIIW-KRWDZBQOSA-N",
"smiles": "CCOC(=O)c1cnn([C@H]2CCOC2)c1-c1ccc(-c2c(C)cnc(OC)c2C)cc1F"
},
"smiles": "CCOC(=O)c1cnn([C@H]2CCOC2)c1-c1ccc(-c2c(C)cnc(OC)c2C)cc1F",
"reactionStepId": "sa_1a300bfdfcc6819a63c4686a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160046623A1;0183;1839179\",\"rsmi\":\"CC1(C)OB([c:12]2[cH:11][c:9]([F:10])[c:8](-[c:7]3[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:32][n:31][n:25]3[C@H:26]3[CH2:27][CH2:28][O:29][CH2:30]3)[cH:24][cH:23]2)OC1(C)C.I[c:13]1[c:14]([CH3:15])[c:16]([O:17][CH3:18])[n:19][cH:20][c:21]1[CH3:22]>C1COCCO1.O.O=C(O)O.[Cs+].[Cs+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[c:9]([F:10])[cH:11][c:12](-[c:13]3[c:14]([CH3:15])[c:16]([O:17][CH3:18])[n:19][cH:20][c:21]3[CH3:22])[cH:23][cH:24]2)[n:25]([C@H:26]2[CH2:27][CH2:28][O:29][CH2:30]2)[n:31][cH:32]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:12]2[cH:11][c:9]([F:10])[c:8](-[c:7]3[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:32][n:31][n:25]3[C@H:26]3[CH2:27][CH2:28][O:29][CH2:30]3)[cH:24][cH:23]2)OC1(C)C.I[c:13]1[c:14]([CH3:15])[c:16]([O:17][CH3:18])[n:19][cH:20][c:21]1[CH3:22]>C1COCCO1.O.O=C(O)O.[Cs+].[Cs+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[c:9]([F:10])[cH:11][c:12](-[c:13]3[c:14]([CH3:15])[c:16]([O:17][CH3:18])[n:19][cH:20][c:21]3[CH3:22])[cH:23][cH:24]2)[n:25]([C@H:26]2[CH2:27][CH2:28][O:29][CH2:30]2)[n:31][cH:32]1\"}",
"reactionStep": {
"id": "sa_1a300bfdfcc6819a63c4686a",
"reactionHash": "b2aed6f2c04b6b45b94cfe428711a9b897110a295a6cc47a8b1519c70e18ac00"
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"children": [
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"moleculeId": "sa_580c83574ef798a3e860141b",
"parentId": "9186",
"isLeaf": false,
"molecule": {
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"inchikey": "GUTLDPBAZXZWKD-HNNXBMFYSA-N",
"smiles": "CCOC(=O)c1cnn([C@H]2CCOC2)c1-c1ccc(B2OC(C)(C)C(C)(C)O2)cc1F"
},
"smiles": "CCOC(=O)c1cnn([C@H]2CCOC2)c1-c1ccc(B2OC(C)(C)C(C)(C)O2)cc1F",
"reactionStepId": "sa_81921c61159c5e43dbd74b0e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160046623A1;0181;1839178\",\"rsmi\":\"Br[c:12]1[cH:11][c:9]([F:10])[c:8](-[c:7]2[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:31][n:30][n:24]2[C@H:25]2[CH2:26][CH2:27][O:28][CH2:29]2)[cH:23][cH:22]1.CC1(C)OB([B:13]2[O:14][C:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[O:21]2)OC1(C)C>CC(=O)O.[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[c:9]([F:10])[cH:11][c:12]([B:13]3[O:14][C:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[O:21]3)[cH:22][cH:23]2)[n:24]([C@H:25]2[CH2:26][CH2:27][O:28][CH2:29]2)[n:30][cH:31]1\"},\"mapped_reaction_smiles\":\"Br[c:12]1[cH:11][c:9]([F:10])[c:8](-[c:7]2[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:31][n:30][n:24]2[C@H:25]2[CH2:26][CH2:27][O:28][CH2:29]2)[cH:23][cH:22]1.CC1(C)OB([B:13]2[O:14][C:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[O:21]2)OC1(C)C>CC(=O)O.[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[c:9]([F:10])[cH:11][c:12]([B:13]3[O:14][C:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[O:21]3)[cH:22][cH:23]2)[n:24]([C@H:25]2[CH2:26][CH2:27][O:28][CH2:29]2)[n:30][cH:31]1\"}",
"reactionStep": {
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"reactionHash": "20b3abe8666951af13c0b61f4c62d60f9a27f4310255d64bd38d946b959ef902"
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"children": [
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"moleculeId": "sa_619a11dfcad08aa644b53bc7",
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"molecule": {
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},
"smiles": "CCOC(=O)c1cnn([C@H]2CCOC2)c1-c1ccc(Br)cc1F",
"reactionStepId": null,
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{
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"molecule": {
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"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
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{
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"molecule": {
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"inchikey": "ZYDSBNIUTYENQC-UHFFFAOYSA-N",
"smiles": "COc1ncc(C)c(I)c1C"
},
"smiles": "COc1ncc(C)c(I)c1C",
"reactionStepId": "sa_8cc8f37425955a11446a4593",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160046623A1;0172;1839177\",\"rsmi\":\"F[c:3]1[n:4][cH:5][c:6]([CH3:7])[c:8]([I:9])[c:10]1[CH3:11].[CH3:1][OH:2]>C1CCOC1.CO.[Na+]>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[c:8]([I:9])[c:10]1[CH3:11]\"},\"mapped_reaction_smiles\":\"F[c:3]1[n:4][cH:5][c:6]([CH3:7])[c:8]([I:9])[c:10]1[CH3:11].[CH3:1][OH:2]>C1CCOC1.CO.[Na+]>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[c:8]([I:9])[c:10]1[CH3:11]\"}",
"reactionStep": {
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"children": [
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"molecule": {
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"smiles": "Cc1cnc(F)c(C)c1I"
},
"smiles": "Cc1cnc(F)c(C)c1I",
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},
{
"id": "9192",
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"molecule": {
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"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
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}
]
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]
}
]
},
{
"id": "9193",
"routeId": "sa_0e5644d021663a192fc9dc9e",
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"molecule": {
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"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
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