ChemFOnt: Showing chemical card for 4-O-Methylgallic acid (CFc000008240)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:55 UTC

Chemfont ID

CFc000008240

Molecule Identification

Common Name

4-O-Methylgallic acid

Definition

4-O-Methyl gallic acid (4-OMGA) has first been identified as a major methyl derivative of gallic acid in human plasma and urine. More recently, 4-O-methyl gallic acid (4-OMGA) has been found in urine during regular black tea ingestion and in plasma after moderate red wine consumption. PMID: 15527792 . 4-O-methylgallic acid (4-OMGA), a major metabolite of gallic acid abundant in red wine. 4-OMGA inhibited the expression of intercellular adhesion molecule-1(ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1) in human umbilical vein endothelial cells (HUVECs) stimulated with tumor necrosis factor-alpha (TNF-alpha), resulting in the suppression of leukocyte adhesion to HUVECs (PMID: 17027748 ). 4-O-Methyl gallic acid has been found to be a metabolite of Beauveria and Pantoea (PMID: 17111140 ) (https://www.researchgate.net/publication/275561863_Microbial_Degradation_of_Bergenin_a_Phenolic_C-Glucoside).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-O-Methylgallate	Generator
3,5-Dihydroxy-4-methoxybenzoic acid	MeSH
4-Methoxy-3,5-dihydroxybenzoic acid	MeSH
4-Methoxygallic acid	MeSH
4OMGA CPD	MeSH
4-Methoxygallate	Generator, HMDB
3,5-Dihydroxy-4-methoxy-benzoate	HMDB
3,5-Dihydroxy-4-methoxy-benzoic acid	HMDB
3,5-Dihydroxy-4-methoxybenzoate	HMDB, Generator
3,5-Dihydroxy-P-anisic acid	HMDB
4-Methoxy-3,5-dihydroxybenzoate	HMDB
5-Hydroxyisovanillic acid	HMDB
4-O-Methylgallic acid	MeSH

Chemical Formula

C₈H₈O₅

Average Molecular Weight

184.1461

Monoisotopic Molecular Weight

184.037173366

IUPAC Name

3,5-dihydroxy-4-methoxybenzoic acid

Traditional Name

3,5-dihydroxy-4-methoxybenzoic acid

CAS Registry Number

4319-02-2

SMILES

COC1=C(O)C=C(C=C1O)C(O)=O

InChI Identifier

InChI=1S/C8H8O5/c1-13-7-5(9)2-4(8(11)12)3-6(7)10/h2-3,9-10H,1H3,(H,11,12)

InChI Key

UBXDWYFLYYJQFR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acid and derivatives

Alternative Parents

Substituents

Gallic acid or derivatives
P-methoxybenzoic acid or derivatives
Methoxyphenol
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Resorcinol
Phenol ether
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 19812218)

Excreta

Biofluid or Excreta

Urine (PMID: 16870009)
Feces (PMID: 24010549)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013198)

Source

Endogenous

Endogenous (HMDB: HMDB0013198)

Plant

Plant (HMDB: HMDB0013198)

Fungi

Beauveria sulfurescens (HMDB: HMDB0013198)

Exogenous

Food

Food (HMDB: HMDB0013198)
Legumes (HMDB: HMDB0013198)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0013198)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0013198)

Tea

Tea products (HMDB: HMDB0013198)

Fat and oil

Olive oil (HMDB: HMDB0013198)

Fruit

Fruits (HMDB: HMDB0013198)

Other fruit

Date (FooDB: FOOD00135)

Vegetable

Vegetables (HMDB: HMDB0013198)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0013198)

Nut

Nuts (HMDB: HMDB0013198)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0013198)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.93 g/L	ALOGPS
logP	1.32	ALOGPS
logP	0.87	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.93	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.74 m³·mol⁻¹	ChemAxon
Polarizability	16.72 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013198

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001960

KNApSAcK ID

Not Available

Chemspider ID

70398

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78016

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4-O-Methylgallic acid (CFc000008240)

MOL for CFc000008240 (4-O-Methylgallic acid)

3D MOL for CFc000008240 (4-O-Methylgallic acid)

3D SDF for CFc000008240 (4-O-Methylgallic acid)

3D-SDF for CFc000008240 (4-O-Methylgallic acid)

PDB for CFc000008240 (4-O-Methylgallic acid)

3D PDB for CFc000008240 (4-O-Methylgallic acid)

SMILES for CFc000008240 (4-O-Methylgallic acid)

INCHI for CFc000008240 (4-O-Methylgallic acid)

Structure for CFc000008240 (4-O-Methylgallic acid)

3D Structure for CFc000008240 (4-O-Methylgallic acid)