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
St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor.	2000 Jun 20	10852961
St John's wort, a herbal antidepressant, activates the steroid X receptor.	2000 Sep	10974665
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	14633740
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	15095150
Induction of human CYP2C9 by rifampicin, hyperforin, and phenobarbital is mediated by the pregnane X receptor.	2004 Feb	14600250
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	15622447
No relevant interaction with alprazolam, caffeine, tolbutamide, and digoxin by treatment with a low-hyperforin St John's wort extract.	2005 Apr	15856409
Potential for interaction of kava and St. John's wort with drugs.	2005 Aug 22	16005588
Possible involvement of pregnane X receptor-enhanced CYP24 expression in drug-induced osteomalacia.	2005 Jan	15630458
MDR- and CYP3A4-mediated drug-herbal interactions.	2006 Mar 27	16442130
Hyperforin--a key constituent of St. John's wort specifically activates TRPC6 channels.	2007 Dec	17666455
HepaRG cells as an in vitro model for evaluation of cytochrome P450 induction in humans.	2008 Jan	17954527
Release of acetylcholinesterase (AChE) from beta-amyloid plaques assemblies improves the spatial memory impairments in APP-transgenic mice.	2008 Sep 25	18599028
A prolonged protein kinase C-mediated, opioid-related antinociceptive effect of st John's Wort in mice.	2010 Feb	19945352
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	20079722
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	21561094
Improved assays for xenosensor activation based on reverse transfection.	2015 Oct	26187274

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:44:01 UTC 2023` Edited by `admin` on `Fri Dec 15 19:44:01 UTC 2023`
Record UNII	RM741E34FP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

Common Name

English

HYPERFORIN [MI]

Common Name

English

Classification Tree Code System Code

DSLD

1122 (Number of products:1)