ganoderic acid F   Click here for help

GtoPdb Ligand ID: 13595

Synonyms: compound 19 [PMID: 24974349] | ganoderate F
Compound class: Synthetic organic
Comment: Ganoderic acid F is a fungus-derived triterpenoid. It has been identified in Ganoderma applanatum (bracket fungus), and is one of the compounds contained in the traditional Chinese medicine Fuzheng Yiliu decoction (FZYLD) [1]. Molecular docking studies revealed potential binding to human tumor necrosis factor-α (TNF-α), which was validated by the compound's biological activity in vitro (anticancer effect in human HepG2 hematoma cancer cells) [1].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 148.95
Molecular weight 570.67
XLogP 1.09
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES C[C@H](CC(=O)CC(C)C(=O)O)[C@H]1CC(=O)[C@@]2(C)C3=C(C(=O)[C@H]([C@]12C)OC(=O)C)[C@@]4(C)CCC(=O)C(C)(C)[C@@H]4CC3=O
Isomeric SMILES C[C@H](CC(=O)CC(C)C(=O)O)[C@H]1CC(=O)[C@@]2([C@@]1([C@@H](C(=O)C3=C2C(=O)C[C@@H]4[C@@]3(CCC(=O)C4(C)C)C)OC(=O)C)C)C
InChI InChI=1S/C32H42O9/c1-15(11-18(34)12-16(2)28(39)40)19-13-23(37)32(8)24-20(35)14-21-29(4,5)22(36)9-10-30(21,6)25(24)26(38)27(31(19,32)7)41-17(3)33/h15-16,19,21,27H,9-14H2,1-8H3,(H,39,40)/t15-,16?,19-,21+,27-,30+,31+,32+/m1/s1
InChI Key BWCNWXLKMWWVBT-AIMUVTGPSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(6R)-6-[(5R,10S,12S,13R,14R,17R)-12-acetyloxy-4,4,10,13,14-pentamethyl-3,7,11,15-tetraoxo-2,5,6,12,16,17-hexahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic acid
Synonyms Click here for help
compound 19 [PMID: 24974349] | ganoderate F
Database Links Click here for help
BindingDB Ligand 50021403
CAS Registry No. 98665-15-7 (source: PubChem)
ChEBI CHEBI:142258
ChEMBL Ligand CHEMBL453981
GtoPdb PubChem SID 504705414
PubChem CID 23247895
Search Google for chemical match using the InChIKey BWCNWXLKMWWVBT-AIMUVTGPSA-N
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UniChem Compound Search for chemical match using the InChIKey BWCNWXLKMWWVBT-AIMUVTGPSA-N
UniChem Connectivity Search for chemical match using the InChIKey BWCNWXLKMWWVBT-AIMUVTGPSA-N