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
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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5189 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12785732 |
10.49 µM [IC50] | ||
Target ID: CHEMBL2095231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27775589 |
10.7 µM [IC50] | ||
Target ID: CHEMBL1681616 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25645827 |
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Target ID: CHEMBL6093 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23969848 |
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Target ID: CHEMBL6023 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23054715 |
43.0 µM [IC50] | ||
Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23054715 |
14.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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 |
|
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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25645827
Mice: 0.2 mg/kg (5 ug per mice) single dose
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15305003
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
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admin
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Edited
Fri Dec 15 17:59:48 GMT 2023
by
admin
on
Fri Dec 15 17:59:48 GMT 2023
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Record UNII |
O2H2Z421AP
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Record Status |
Validated (UNII)
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Record Version |
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Citreorosein
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O2H2Z421AP
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DTXSID60197420
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481-73-2
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361512
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