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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 of .OMEGA.-HYDROXYEMODIN

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

Molecular Formula C15H10O6
Molecular Weight 286.2363
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.49 µM [IC50]
10.7 µM [IC50]
43.0 µM [IC50]
14.0 µM [IC50]
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
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
Biotransformation of the anthraquinones emodin and chrysophanol by cytochrome P450 enzymes. Bioactivation to genotoxic metabolites.
1998 Jun
Six immunosuppressive features from an ascomycete, Zopfiella longicaudata, found in a screening study monitored by immunomodulatory activity.
2004 Aug
Patents

Sample Use Guides

Mice: 0.2 mg/kg (5 ug per mice) single dose
Route of Administration: Other
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:59:48 GMT 2023
Edited
by admin
on Fri Dec 15 17:59:48 GMT 2023
Record UNII
O2H2Z421AP
Record Status Validated (UNII)
Record Version
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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
Created by admin on Fri Dec 15 17:59:48 GMT 2023 , Edited by admin on Fri Dec 15 17:59:48 GMT 2023
PRIMARY
FDA UNII
O2H2Z421AP
Created by admin on Fri Dec 15 17:59:48 GMT 2023 , Edited by admin on Fri Dec 15 17:59:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID60197420
Created by admin on Fri Dec 15 17:59:48 GMT 2023 , Edited by admin on Fri Dec 15 17:59:48 GMT 2023
PRIMARY
NSC
624612
Created by admin on Fri Dec 15 17:59:48 GMT 2023 , Edited by admin on Fri Dec 15 17:59:48 GMT 2023
PRIMARY
CAS
481-73-2
Created by admin on Fri Dec 15 17:59:48 GMT 2023 , Edited by admin on Fri Dec 15 17:59:48 GMT 2023
PRIMARY
PUBCHEM
361512
Created by admin on Fri Dec 15 17:59:48 GMT 2023 , Edited by admin on Fri Dec 15 17:59:48 GMT 2023
PRIMARY
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