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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 of 3-O-METHYLGALANGIN

SMILES

COC1=C(OC2=CC(O)=CC(O)=C2C1=O)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

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q6P8U6
Gene ID: 69060.0
Gene Symbol: Pnlip
Target Organism: Mus musculus (Mouse)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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 Dec
Heliotropium huascoense resin exudate: chemical constituents and defensive properties.
2001 Sep
3-Methylethergalangin isolated from Alpinia officinarum inhibits pancreatic lipase.
2003 Jun
New dihydrochalcones and anti-platelet aggregation constituents from the leaves of Muntingia calabura.
2007 Jun
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 Jun 2
Structure-Activity and Lipophilicity Relationships of Selected Antibacterial Natural Flavones and Flavanones of Chilean Flora.
2017 Apr 10
Patents

Sample Use Guides

Mice: 10 and 20 mg/kg for 3 days
Route of Administration: Oral
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 Fri Dec 15 18:50:58 GMT 2023
Edited
by admin
on Fri Dec 15 18:50:58 GMT 2023
Record UNII
02887TX99X
Record Status Validated (UNII)
Record Version
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Name Type Language
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
3-METHYLGALANGIN
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
Created by admin on Fri Dec 15 18:50:58 GMT 2023 , Edited by admin on Fri Dec 15 18:50:58 GMT 2023
PRIMARY
CHEBI
1602
Created by admin on Fri Dec 15 18:50:58 GMT 2023 , Edited by admin on Fri Dec 15 18:50:58 GMT 2023
PRIMARY
FDA UNII
02887TX99X
Created by admin on Fri Dec 15 18:50:58 GMT 2023 , Edited by admin on Fri Dec 15 18:50:58 GMT 2023
PRIMARY
PUBCHEM
5281946
Created by admin on Fri Dec 15 18:50:58 GMT 2023 , Edited by admin on Fri Dec 15 18:50:58 GMT 2023
PRIMARY
CAS
6665-74-3
Created by admin on Fri Dec 15 18:50:58 GMT 2023 , Edited by admin on Fri Dec 15 18:50:58 GMT 2023
PRIMARY