HYPERFORIN

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 Search

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

Title	Date	PubMed
Improved assays for xenosensor activation based on reverse transfection.	2015-10	26187274
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.	2011-06-23	21561094
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	20079722
A prolonged protein kinase C-mediated, opioid-related antinociceptive effect of st John's Wort in mice.	2010-02	19945352
Release of acetylcholinesterase (AChE) from beta-amyloid plaques assemblies improves the spatial memory impairments in APP-transgenic mice.	2008-09-25	18599028
HepaRG cells as an in vitro model for evaluation of cytochrome P450 induction in humans.	2008-01	17954527
Hyperforin--a key constituent of St. John's wort specifically activates TRPC6 channels.	2007-12	17666455
MDR- and CYP3A4-mediated drug-herbal interactions.	2006-03-27	16442130
Potential for interaction of kava and St. John's wort with drugs.	2005-08-22	16005588
No relevant interaction with alprazolam, caffeine, tolbutamide, and digoxin by treatment with a low-hyperforin St John's wort extract.	2005-04	15856409
Possible involvement of pregnane X receptor-enhanced CYP24 expression in drug-induced osteomalacia.	2005-01	15630458
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.	2004-11	15622447
In vitro interaction of the HIV protease inhibitor ritonavir with herbal constituents: changes in P-gp and CYP3A4 activity.	2004-07-22	15266218
Induction and inhibition of cytochromes P450 by the St. John's wort constituent hyperforin in human hepatocyte cultures.	2004-05	15100173
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.	2004-04	15095150
Induction of human CYP2C9 by rifampicin, hyperforin, and phenobarbital is mediated by the pregnane X receptor.	2004-02	14600250
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.	2003-11-15	14633740
St John's wort, a herbal antidepressant, activates the steroid X receptor.	2000-09	10974665
St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor.	2000-06-20	10852961

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:55:18 GMT 2025` Edited by `admin` on `Mon Mar 31 19:55:18 GMT 2025`
Record UNII	RM741E34FP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(+)-HYPERFORIN

Preferred Name

English

HYPERFORIN

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 [MI]

Common Name

English

Classification Tree Code System Code

DSLD

1122 (Number of products:1)