enoxolone   Click here for help

GtoPdb Ligand ID: 11264

Synonyms: 18β-Glycyrrhetinic acid | glycyrrhetic acid | glycyrrhetinic acid
PDB Ligand
Compound class: Synthetic organic
Comment: Enoxolone is a bioactive metabolite of glycyrrhizin, which is a compound found in the liquorice plant Glycyrrhiza glabra. It has been found to inhibit enzymes that metabolise the prostaglandins PGE2 and PGF to their inactive metabolites, and 11β-hydroxysteroid dehydrogenases (HSD11B1, HSD11B2) which convert active cortisol to inactive cortisone. Enoxolone has proposed anti-inflammatory [4-5,7,9] and antitussive effects as well as action against pathogens (viruses, fungal infections, bacterial infections) [1,3], and beneficial actions for the treatmant of gastric ulcers.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 74.6
Molecular weight 470.34
XLogP 6.75
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES O=C1C=C2[C@@H]3C[C@](C)(CC[C@]3(C)CC[C@]2([C@]2([C@H]1[C@@]1(C)CC[C@@H](C([C@@H]1CC2)(C)C)O)C)C)C(=O)O
Isomeric SMILES O=C1C=C2[C@@H]3C[C@](C)(CC[C@]3(C)CC[C@]2([C@]2([C@H]1[C@@]1(C)CC[C@@H](C([C@@H]1CC2)(C)C)O)C)C)C(=O)O
InChI InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1
InChI Key MPDGHEJMBKOTSU-YKLVYJNSSA-N
Classification Click here for help
Compound class Synthetic organic
International Nonproprietary Names Click here for help
INN number INN
1794 enoxolone
Synonyms Click here for help
18β-Glycyrrhetinic acid | glycyrrhetic acid | glycyrrhetinic acid
Database Links Click here for help
BindingDB Ligand 50233538
CAS Registry No. 471-53-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL230006
DrugBank Ligand DB13089
DrugCentral Ligand 3178
GtoPdb PubChem SID 434321699
PubChem CID 10114
RCSB PDB Ligand CBW
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