ChemFOnt: Showing chemical card for Guggulsterone (CFc000001692)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:23 UTC

Chemfont ID

CFc000001692

Molecule Identification

Common Name

Guggulsterone

Definition

Guggulsterone is an ingredient in many nutritional supplements. Guggulsterone is a plant sterol derived from the gum resin (guggulu) of the tree Commiphora mukul. This sterol can inhibit NF-κB activation and downregulate the expression of inflammatory gene products such as COX-2 and MMP-9, which are major players in the development of arthritis. Guggulsterone also can suppress osteoclastogenesis induced by RANKL (receptor activator of NF-κB ligand), a bone-resorbing cytokine. The anti-inflammatory activity of C. mukul (guggul) has been compared with that of NSAIDs, namely phenylbutazone and ibuprofen. Guggulsterone is used to treat obesity, diabetes, hyperlipidemia, atherosclerosis, and osteoarthritis, and has been recently shown to antagonize the farnesoid X receptor and decrease the expression of bile acid-activated genes. It modulates activation of NF-kappaB, which has been closely linked with inflammatory diseases affected by guggulsterone. (PMID: 17475558 , 15322087 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(8XI,9xi,14xi,17E)-20-methoxypregna-4,17-diene-3,16-dione	HMDB
20-Methoxy-4,17(20)e-pregnadiene-3,16-dione	HMDB
4,17(20)-Pregnadiene-3,16-dione	HMDB
Guggulsterone-m	HMDB

Chemical Formula

C₂₂H₃₀O₃

Average Molecular Weight

342.4718

Monoisotopic Molecular Weight

342.219494826

IUPAC Name

(1R,2R,10S,11S,14E,15S)-14-(1-methoxyethylidene)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,13-dione

Traditional Name

(Z)-guggulsterone

CAS Registry Number

95975-55-6

SMILES

[H][C@@]12CC(=O)\C(=C(/C)OC)[C@@]1(C)CC[C@]1([H])[C@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C22H30O3/c1-13(25-4)20-19(24)12-18-16-6-5-14-11-15(23)7-9-21(14,2)17(16)8-10-22(18,20)3/h11,16-18H,5-10,12H2,1-4H3/b20-13-/t16-,17+,18-,21-,22-/m0/s1

InChI Key

WOVLRQSWILBDQL-IABMEBKLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
16-oxosteroid
Delta-4-steroid
Cyclohexenone
Vinylogous ester
Cyclic ketone
Ketone
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002726)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0002726)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002726)

Source

Endogenous

Endogenous (HMDB: HMDB0002726)

Animal

Animal (HMDB: HMDB0002726)

Exogenous

Food

Food (HMDB: HMDB0002726)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0002726)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0002726)

Molecular messenger

Hormone (HMDB: HMDB0002726)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002726)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0099 g/L	ALOGPS
logP	3.5	ALOGPS
logP	3.46	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	18.96	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	100.48 m³·mol⁻¹	ChemAxon
Polarizability	39.54 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0002726

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023055

KNApSAcK ID

C00047241

Chemspider ID

558777

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Guggulsterone

METLIN ID

Not Available

PubChem Compound

643658

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Guggulsterone (CFc000001692)

MOL for CFc000001692 (Guggulsterone)

3D MOL for CFc000001692 (Guggulsterone)

3D SDF for CFc000001692 (Guggulsterone)

3D-SDF for CFc000001692 (Guggulsterone)

PDB for CFc000001692 (Guggulsterone)

3D PDB for CFc000001692 (Guggulsterone)

SMILES for CFc000001692 (Guggulsterone)

INCHI for CFc000001692 (Guggulsterone)

Structure for CFc000001692 (Guggulsterone)

3D Structure for CFc000001692 (Guggulsterone)