U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C35H52O4
Molecular Weight 536.785
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYPERFORIN

SMILES

CC(C)C(=O)[C@]12C(=O)[C@](CC=C(C)C)(C[C@H](CC=C(C)C)[C@@]1(C)CCC=C(C)C)C(=O)C(CC=C(C)C)=C2O

InChI

InChIKey=IWBJJCOKGLUQIZ-HQKKAZOISA-N
InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,38H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1

HIDE SMILES / InChI

Molecular Formula C35H52O4
Molecular Weight 536.785
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor.
2000 Jun 20
St John's wort, a herbal antidepressant, activates the steroid X receptor.
2000 Sep
St. John's wort extracts and some of their constituents potently inhibit ultimate carcinogen formation from benzo[a]pyrene-7,8-dihydrodiol by human CYP1A1.
2003 Nov 15
Proteome analysis reveals a distinct molecular profile of cellular stress following incubation of DDT1-MF2 smooth muscle cells in the presence of a high concentration of hyperforin.
2004 Apr
Induction of human CYP2C9 by rifampicin, hyperforin, and phenobarbital is mediated by the pregnane X receptor.
2004 Feb
In vitro interaction of the HIV protease inhibitor ritonavir with herbal constituents: changes in P-gp and CYP3A4 activity.
2004 Jul-Aug
Induction and inhibition of cytochromes P450 by the St. John's wort constituent hyperforin in human hepatocyte cultures.
2004 May
Hyperforin, the active component of St. John's wort, induces IL-8 expression in human intestinal epithelial cells via a MAPK-dependent, NF-kappaB-independent pathway.
2004 Nov
No relevant interaction with alprazolam, caffeine, tolbutamide, and digoxin by treatment with a low-hyperforin St John's wort extract.
2005 Apr
Potential for interaction of kava and St. John's wort with drugs.
2005 Aug 22
Possible involvement of pregnane X receptor-enhanced CYP24 expression in drug-induced osteomalacia.
2005 Jan
MDR- and CYP3A4-mediated drug-herbal interactions.
2006 Mar 27
Hyperforin--a key constituent of St. John's wort specifically activates TRPC6 channels.
2007 Dec
HepaRG cells as an in vitro model for evaluation of cytochrome P450 induction in humans.
2008 Jan
Release of acetylcholinesterase (AChE) from beta-amyloid plaques assemblies improves the spatial memory impairments in APP-transgenic mice.
2008 Sep 25
A prolonged protein kinase C-mediated, opioid-related antinociceptive effect of st John's Wort in mice.
2010 Feb
Enhanced steatosis by nuclear receptor ligands: a study in cultured human hepatocytes and hepatoma cells with a characterized nuclear receptor expression profile.
2010 Mar 30
Synthesis of novel vitamin K2 analogues with modification at the ω-terminal position and their biological evaluation as potent steroid and xenobiotic receptor (SXR) agonists.
2011 Jun 23
Improved assays for xenosensor activation based on reverse transfection.
2015 Oct
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:44:01 GMT 2023
Edited
by admin
on Fri Dec 15 19:44:01 GMT 2023
Record UNII
RM741E34FP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYPERFORIN
HSDB   MI   WHO-DD  
Common Name English
HYPERFORIN (CONSTITUENT OF ST. JOHN'S WORT) [DSC]
Common Name English
Hyperforin [WHO-DD]
Common Name English
BICYCLO(3.3.1)NON-3-ENE-2,9-DIONE, 4-HYDROXY-6-METHYL-1,3,7-TRIS(3-METHYL-2-BUTEN-1-YL)-5-(2-METHYL-1-OXOPROPYL)-6-(4-METHYL-3-PENTEN-1-YL)-, (1R,5S,6R,7S)-
Systematic Name English
HYPERFORIN [HSDB]
Common Name English
(+)-HYPERFORIN
Common Name English
HYPERFORIN [MI]
Common Name English
Classification Tree Code System Code
DSLD 1122 (Number of products:1)
Created by admin on Fri Dec 15 19:44:01 GMT 2023 , Edited by admin on Fri Dec 15 19:44:01 GMT 2023
Code System Code Type Description
CHEBI
5834
Created by admin on Fri Dec 15 19:44:01 GMT 2023 , Edited by admin on Fri Dec 15 19:44:01 GMT 2023
PRIMARY
CAS
11079-53-1
Created by admin on Fri Dec 15 19:44:01 GMT 2023 , Edited by admin on Fri Dec 15 19:44:01 GMT 2023
PRIMARY
MERCK INDEX
m6171
Created by admin on Fri Dec 15 19:44:01 GMT 2023 , Edited by admin on Fri Dec 15 19:44:01 GMT 2023
PRIMARY Merck Index
MESH
C001654
Created by admin on Fri Dec 15 19:44:01 GMT 2023 , Edited by admin on Fri Dec 15 19:44:01 GMT 2023
PRIMARY
HSDB
7646
Created by admin on Fri Dec 15 19:44:01 GMT 2023 , Edited by admin on Fri Dec 15 19:44:01 GMT 2023
PRIMARY
DRUG BANK
DB01892
Created by admin on Fri Dec 15 19:44:01 GMT 2023 , Edited by admin on Fri Dec 15 19:44:01 GMT 2023
PRIMARY
EPA CompTox
DTXSID90891409
Created by admin on Fri Dec 15 19:44:01 GMT 2023 , Edited by admin on Fri Dec 15 19:44:01 GMT 2023
PRIMARY
EVMPD
SUB183753
Created by admin on Fri Dec 15 19:44:01 GMT 2023 , Edited by admin on Fri Dec 15 19:44:01 GMT 2023
PRIMARY
SMS_ID
100000169967
Created by admin on Fri Dec 15 19:44:01 GMT 2023 , Edited by admin on Fri Dec 15 19:44:01 GMT 2023
PRIMARY
FDA UNII
RM741E34FP
Created by admin on Fri Dec 15 19:44:01 GMT 2023 , Edited by admin on Fri Dec 15 19:44:01 GMT 2023
PRIMARY
WIKIPEDIA
HYPERFORIN
Created by admin on Fri Dec 15 19:44:01 GMT 2023 , Edited by admin on Fri Dec 15 19:44:01 GMT 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR