Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H28O2 |
| Molecular Weight | 312.4458 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C\C=C1\C(=O)C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI
InChIKey=WDXRGPWQVHZTQJ-AUKWTSKRSA-N
InChI=1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/b16-4-/t15-,17+,18+,20+,21-/m1/s1
| Molecular Formula | C21H28O2 |
| Molecular Weight | 312.4458 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11988537 | https://www.ncbi.nlm.nih.gov/pubmed/12089353https://www.ncbi.nlm.nih.gov/pubmed/16250653Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26337021 | https://www.ncbi.nlm.nih.gov/pubmed/17292610 | https://www.ncbi.nlm.nih.gov/pubmed/23688559 | https://www.ncbi.nlm.nih.gov/pubmed/26879835
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11988537 | https://www.ncbi.nlm.nih.gov/pubmed/12089353https://www.ncbi.nlm.nih.gov/pubmed/16250653
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26337021 | https://www.ncbi.nlm.nih.gov/pubmed/17292610 | https://www.ncbi.nlm.nih.gov/pubmed/23688559 | https://www.ncbi.nlm.nih.gov/pubmed/26879835
(Z)-Guggulsterone is a natural product that lowers cholesterol due to its function as an antagonist ligand for the bile acid receptor. (Z)-Guggulsterone is a nuclear hormone receptor that regulates the transcription of several genes involved in cholesterol metabolism and plays a role in cholesterol level regulation. (Z)-Guggulsterone is also a selective farnesoid X receptor (FXR) modulator. Both Guggulsterone isomers were demonstrated to suppress lipopolysaccharide-induced inflammation by inhibiting IκB-α degradation and NF-κB activation. GS has medicinal properties such as anti-inflammatory, hepatoprotective, muscle relaxing, hypocholesterolemic and anti-obesity, antimycobacterial, antischistomal, larvicidal, and molluscicida.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12089353http://www.sciencedirect.com/science/article/pii/S004040200193577X?via%3Dihub
Curator's Comment: The laboratory of the Dr. Sukh Dev the first isolated of Z- and E-guggulsterones from guggulipid in 1971.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q96RI1 Gene ID: 9971.0 Gene Symbol: NR1H4 Target Organism: Homo sapiens (Human) |
|||
Target ID: CHEMBL2047 |
12.0 nM [IC50] | ||
Target ID: CHEMBL1871 |
660.0 nM [EC50] | ||
Target ID: CHEMBL2034 |
6060.0 nM [IC50] | ||
Target ID: CHEMBL1994 |
1880.0 nM [IC50] | ||
Target ID: CHEMBL3401 |
2.4 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Suppression of the pregnane X receptor during endoplasmic reticulum stress is achieved by down-regulating hepatocyte nuclear factor-4α and up-regulating liver-enriched inhibitory protein. | 2015-04 |
|
| Alisol B 23-acetate protects against ANIT-induced hepatotoxity and cholestasis, due to FXR-mediated regulation of transporters and enzymes involved in bile acid homeostasis. | 2015-03-15 |
|
| Expression of DNA methyltransferases in breast cancer patients and to analyze the effect of natural compounds on DNA methyltransferases and associated proteins. | 2013-03 |
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| Identification of UV-protective activators of nuclear factor erythroid-derived 2-related factor 2 (Nrf2) by combining a chemical library screen with computer-based virtual screening. | 2012-09-21 |
|
| Discovery of sulfated sterols from marine invertebrates as a new class of marine natural antagonists of farnesoid-X-receptor. | 2011-03-10 |
|
| Regulation of human carbonyl reductase 3 (CBR3; SDR21C2) expression by Nrf2 in cultured cancer cells. | 2010-10-05 |
|
| Enhanced steatosis by nuclear receptor ligands: a study in cultured human hepatocytes and hepatoma cells with a characterized nuclear receptor expression profile. | 2010-03-30 |
|
| Enhanced effects of guggulsterone plus 1,25(OH)2D3 on 3T3-L1 adipocytes. | 2007-12-21 |
|
| Guggulsterone inhibits tumor cell proliferation, induces S-phase arrest, and promotes apoptosis through activation of c-Jun N-terminal kinase, suppression of Akt pathway, and downregulation of antiapoptotic gene products. | 2007-06-30 |
|
| The ratio of constitutive androstane receptor to pregnane X receptor determines the activity of guggulsterone against the Cyp2b10 promoter. | 2005-07 |
|
| Megalin and cubilin expression in gallbladder epithelium and regulation by bile acids. | 2004-12 |
|
| Guggulsterone inhibits NF-kappaB and IkappaBalpha kinase activation, suppresses expression of anti-apoptotic gene products, and enhances apoptosis. | 2004-11-05 |
|
| Guggulsterone activates multiple nuclear receptors and induces CYP3A gene expression through the pregnane X receptor. | 2004-08 |
|
| Guggulsterone antagonizes farnesoid X receptor induction of bile salt export pump but activates pregnane X receptor to inhibit cholesterol 7alpha-hydroxylase gene. | 2003-04-25 |
|
| Guggulsterone is a farnesoid X receptor antagonist in coactivator association assays but acts to enhance transcription of bile salt export pump. | 2003-03-21 |
|
| The hypolipidemic natural product guggulsterone acts as an antagonist of the bile acid receptor. | 2002-07 |
|
| A natural product that lowers cholesterol as an antagonist ligand for FXR. | 2002-05-31 |
Patents
Sample Use Guides
in experimental animals: Serum lipids were found to be lowered by Guggulsterone (an 80:20 mixture of the Z- and E-isomers) (50 mgkg, b.w.) in triton WR-1339 induced hyperlipaemia. Chronic feeding of this drug (5 mg/kg, b.w.) in animals simultaneously fed with cholesterol (25 m%kg, b.w.) for 30 days, caused lowering in the lipid and apoprotein levels of very low density and low density lipoproteins in experimental animals.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:54:46 GMT 2025
by
admin
on
Mon Mar 31 19:54:46 GMT 2025
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| Record UNII |
9B259YE66O
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| Record Status |
Validated (UNII)
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| Record Version |
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2405 (Number of products:11)
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6439929
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39025-24-6
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m5878
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