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 PGF2α 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.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
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
Search Google for chemical match using the InChIKey MPDGHEJMBKOTSU-YKLVYJNSSA-N
Search Google for chemicals with the same backbone MPDGHEJMBKOTSU
Search PubMed clinical trials enoxolone
Search PubMed titles enoxolone
Search PubMed titles/abstracts enoxolone
UniChem Compound Search for chemical match using the InChIKey MPDGHEJMBKOTSU-YKLVYJNSSA-N
UniChem Connectivity Search for chemical match using the InChIKey MPDGHEJMBKOTSU-YKLVYJNSSA-N