3-O-METHYLGALANGIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H12O5
Molecular Weight	284.2635
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC2=C(C1=O)C(O)=CC(O)=C2)C3=CC=CC=C3

InChI

InChIKey=LYISDADPVOHJBJ-UHFFFAOYSA-N

InChI=1S/C16H12O5/c1-20-16-14(19)13-11(18)7-10(17)8-12(13)21-15(16)9-5-3-2-4-6-9/h2-8,17-18H,1H3

HIDE SMILES / InChI

Molecular Formula	C16H12O5
Molecular Weight	284.2635
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17516329 | https://www.ncbi.nlm.nih.gov/pubmed/19512999 | https://www.ncbi.nlm.nih.gov/pubmed/28394271 | https://www.ncbi.nlm.nih.gov/pubmed/12808299

3-O-methylgalangin is a naturally-occurring flavonoid. It is isolated and purified from the rhizomes of Alpinia officinarum and flowers of Helichrysum kraussii and H. odoratissimum. 3-O-methylgalangin exhibited significant anti-platelet aggregation activity in vitro. It has antioxidant activity. The higher antioxidant activity 3-O-methylgalangin can be attributed to the presence of C-2-C-3 unsaturation allowing the resonance stabilization of the formed radical. Flavonoids are known for their antimicrobial properties and 3-O-methylgalangin possess antibacterial activity against Gram-positive and Gram-negative bacteria also. 3-O-methylgalangin is an inhibitor of pancreatic lipase and it was reported that it lowered serum triglyceride level on corn oil-induced hyperlipidemic mice.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Pancreatic triacylglycerol lipase 12 Target ID: Q6P8U6 Gene ID: 69060.0 Gene Symbol: Pnlip Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12808299	Inhibitor 8504
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24354185 \| https://www.ncbi.nlm.nih.gov/pubmed/19512999	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hyperlipidemia 82 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12808299	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Structure-Activity and Lipophilicity Relationships of Selected Antibacterial Natural Flavones and Flavanones of Chilean Flora.	2017-04-10	28394271
Antiinflammatory and antioxidant flavonoids from Helichrysum kraussii and H. odoratissimum flowers.	2013-10	24354185
Chemical analysis of the resinous exudate isolated from Heliotropium taltalense and evaluation of the antioxidant activity of the phenolics components and the resin in homogeneous and heterogeneous systems.	2009-06-02	19512999
New dihydrochalcones and anti-platelet aggregation constituents from the leaves of Muntingia calabura.	2007-06	17516329
3-Methylethergalangin isolated from Alpinia officinarum inhibits pancreatic lipase.	2003-06	12808299
Heliotropium huascoense resin exudate: chemical constituents and defensive properties.	2001-09	11575941
Determination of the effect of 8-O-(2-methyl-2-butenoyl)-5,7-dihydroxy-3-methoxyflavone from Gnaphalium robustum on growth of Escherichia coli K-12 by optical density and electrical conductance measurements.	1994-12	7809218

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 10 and 20 mg/kg for 3 days

Route of Administration: Oral

In Vitro Use Guide

To determine the effect of 3-O-methylgalangin on the growth curve of E. coli and B. subtilis, it was added to exponentially-growing cultures. 3-O-methylgalangin decreased the culture turbidity and cell viability of the Gram-positive bacteria Bacillus subtilis with the concentration 0.01 ug/ul. 3-O-methylgalangin showed a MICs that ranged from 0.25 to 1 ug/ml for tested Gram-negative bacteria (Enterobacter cloacae, Escherichia coli, Klebsiella pneumoniae, and Proteus mirabilis) and Gram-positive bacteria (Bacillus cereus, B. subtilis, B. coagulans, and Staphylococcus aureus).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:22:30 GMT 2025` Edited by `admin` on `Mon Mar 31 19:22:30 GMT 2025`
Record UNII	02887TX99X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3-METHYLGALANGIN

Preferred Name

English

3-O-METHYLGALANGIN

Common Name

English

5,7-DIHYDROXY-3-METHOXYFLAVONE

Systematic Name

English

FLAVONE, 5,7-DIHYDROXY-3-METHOXY-

Systematic Name

English

GALANGIN 3-METHYL ETHER

Common Name

English

GALANGIN 3-O-METHYL ETHER

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-3-METHOXY-2-PHENYL-

Systematic Name

English

5,7-DIHYDROXY-3-METHOXY-2-PHENYL-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID20216823