.OMEGA.-HYDROXYEMODIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O6
Molecular Weight	286.2363
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OCC1=CC(O)=C2C(=O)C3=C(C=C(O)C=C3O)C(=O)C2=C1

InChI

InChIKey=YQHZABGPIPECSQ-UHFFFAOYSA-N

InChI=1S/C15H10O6/c16-5-6-1-8-12(10(18)2-6)15(21)13-9(14(8)20)3-7(17)4-11(13)19/h1-4,16-19H,5H2

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23054715 | https://www.ncbi.nlm.nih.gov/pubmed/22154852 | https://www.ncbi.nlm.nih.gov/pubmed/25645827

Omega-hydroxyemodin a naturally occurring anthraquinone derivative isolated from Polygoni cuspidati radix. It has anti-bacterial and phytoestrogen activity. Omega-hydroxyemodin demonstrated topoisomerases I and II inhibition activity. Omega-hydroxyemodin significantly attenuated the DNA binding of activator protein (AP)-1 that regulates COX-2 expression through the reduction of the phosphorylation of c-Jun. Moreover, inhibition of PGD2 generation by Omega-hydroxyemodin was accompanied by a decrease in phosphorylation of cytosolic phospholipase A2α. Taken together, these data suggest that Omega-hydroxyemodin represents a potential therapeutic approach for the treatment of inflammatory diseases. Omega-hydroxyemodin was efficacious in a mouse model of S. aureus skin and soft tissue infections.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Sialidase 1 Target ID: CHEMBL5189 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12785732	Inhibitor 8297	10.49 µM [IC50]
Hepatitis C virus serine protease, NS3/NS4A 13 Target ID: CHEMBL2095231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27775589	Inhibitor 8297	10.7 µM [IC50]
Accessory gene regulator protein A 1 Target ID: CHEMBL1681616 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25645827	Inhibitor 8297
Calmodulin 17 Target ID: CHEMBL6093 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23969848	Inhibitor 8297
Topoisomerase I 4 Target ID: CHEMBL6023 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23054715	Inhibitor 8297	43.0 µM [IC50]
DNA topoisomerase II 66 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23054715	Inhibitor 8297	14.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28509846	Primary	Basic research	Unknown Approved Use Unknown
Skin and soft tissue infections 33 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25645827	Primary	Preclinical	Unknown Approved Use Unknown
Inflammatory diseases 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22154852 https://www.ncbi.nlm.nih.gov/pubmed/22687535	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Studies in the biochemistry of micro-organisms: Emodic acid (4:5:7-trihydroxyanthraquinone-2-carboxylic acid) and omega-hydroxyemodin (4:5:7-trihydroxy-2-(hydroxymethyl)-anthraquinone), metabolic products of a strain of Penicillium cyclopium Westling.	1940 Feb	16747151
omega-Hydroxyemodin, a major hepatic metabolite of emodin in various animals and its mutagenic activity.	1987 Oct	3309636
Biotransformation of the anthraquinones emodin and chrysophanol by cytochrome P450 enzymes. Bioactivation to genotoxic metabolites.	1998 Jun	9616189
Six immunosuppressive features from an ascomycete, Zopfiella longicaudata, found in a screening study monitored by immunomodulatory activity.	2004 Aug	15305003
Studies on chemical constituents of Rheum glabricaule.	2005 Aug	16379418
Pest-managing activities of plant extracts and anthraquinones from Cassia nigricans from Burkina Faso.	2008 Apr	17478091
Anthraquinones from Polygonum cuspidatum as tyrosinase inhibitors for dermal use.	2008 Apr	18338768
Structural elucidation of in vitro metabolites of emodin by liquid chromatography-tandem mass spectrometry.	2008 Nov	18651591
Characterization of emodin metabolites in Raji cells by LC-APCI-MS/MS.	2009 Nov 1	19800244
Biotransformation of paeonol and emodin by transgenic crown galls of Panax quinquefolium.	2010 Mar	19455432

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 0.2 mg/kg (5 ug per mice) single dose

Route of Administration: Other

In Vitro Use Guide

The immunosuppressive activities of Omega-hydroxyemodin were calculated against Con A-induced (T cell) and LPS-induced (B cell) proliferation of mouse splenic lymphocyte. It has moderate immunosuppressive activities with IC(50) values 9.0 ug/ml for Con A-induced (T cell) and LPS-induced (B cell) proliferations.

Name

Type

Language

.OMEGA.-HYDROXYEMODIN

Common Name

English

HYDROXYEMODIN

Common Name

English

9,10-ANTHRACENEDIONE, 1,3,8-TRIHYDROXY-6-(HYDROXYMETHYL)-

Systematic Name

English

NSC-624612

Code

English

OMEGA-HYDROXYEMODIN

Common Name

English

1,3,8-TRIHYDROXY-6-(HYDROXYMETHYL)ANTHRAQUINONE

Systematic Name

English

HYDROXYEMODIN, .OMEGA.-

Common Name

English

ANTHRAQUINONE, 1,3,8-TRIHYDROXY-6-(HYDROXYMETHYL)-

Systematic Name

English

CITREOROSEIN

Common Name

English

1,3,8-TRIHYDROXY-6-HYDROXYMETHYLANTHRAQUINONE

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

Citreorosein