You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-11-30 15:50:49 UTC
Update Date2017-12-07 02:39:30 UTC
HMDB IDHMDB0013198
Secondary Accession Numbers
  • HMDB13198
Metabolite Identification
Common Name4-O-Methylgallic acid
Description4-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 .
Structure
Thumb
Synonyms
ValueSource
4-Methoxygallic acidChEMBL
4-MethoxygallateGenerator
4-O-MethylgallateGenerator
3,5-Dihydroxy-4-methoxy-benzoateHMDB
3,5-Dihydroxy-4-methoxy-benzoic acidHMDB
3,5-Dihydroxy-4-methoxybenzoateHMDB
3,5-Dihydroxy-4-methoxybenzoic acidHMDB
3,5-Dihydroxy-P-anisic acidHMDB
4-Methoxy-3,5-dihydroxybenzoateHMDB
4-Methoxy-3,5-dihydroxybenzoic acidHMDB
5-Hydroxyisovanillic acidHMDB
4OMGA CPDMeSH
Chemical FormulaC8H8O5
Average Molecular Weight184.1461
Monoisotopic Molecular Weight184.037173366
IUPAC Name3,5-dihydroxy-4-methoxybenzoic acid
Traditional Name3,5-dihydroxy-4-methoxybenzoic acid
CAS Registry NumberNot Available
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 KeyUBXDWYFLYYJQFR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as gallic acid and derivatives. These are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentGallic 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 FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.93 g/LALOGPS
logP1.32ALOGPS
logP0.87ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.93ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.74 m³·mol⁻¹ChemAxon
Polarizability16.72 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-1900000000-32a93cf4f7568a9bdedcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-009i-2139000000-adf8b88e8bb85a43cb0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-a129a3b3cfd0493a0408View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-4576c6e0e594b56d93b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-2900000000-19f8938cc76bae18f2e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-886cb3b61676c31904a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0080-0900000000-4bad45b0a4df1de7f271View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-2900000000-17d90b668a07c63b811eView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.04 +/- 0.014 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.029 +/- 0.006 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.05 +/- 0.015 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.057 +/- 0.017 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.025 +/- 0.002 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.023 +/- 0.002 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.02 +/- 0.002 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.084 +/- 0.063 uMAdult (>18 years old)Male
Normal
details
FecesDetected and Quantified6.245 +/- 0.326 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified6.734 +/- 0.706 nmol/g of fecesAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.153 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.211 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.229 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.74 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.407 +/- 0.680 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.440 +/- 0.680 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 923 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 923 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 923 details
UrineDetected and Quantified0.22666 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.29333 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.014 +/- 0.004 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.008 +/- 0.002 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.017 +/- 0.003 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite ID923
FoodDB IDFDB001960
KNApSAcK IDNot Available
Chemspider ID70398
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound78016
PDB IDNot Available
ChEBI ID297061
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Oliveira MV, Badia E, Carbonneau MA, Grimaldi P, Fouret G, Lauret C, Leger CL: Potential anti-atherogenic cell action of the naturally occurring 4-O-methyl derivative of gallic acid on Ang II-treated macrophages. FEBS Lett. 2004 Nov 5;577(1-2):239-44. [PubMed:15527792 ]
  2. Lee G, Na HJ, Namkoong S, Jeong Kwon H, Han S, Ha KS, Kwon YG, Lee H, Kim YM: 4-O-methylgallic acid down-regulates endothelial adhesion molecule expression by inhibiting NF-kappaB-DNA-binding activity. Eur J Pharmacol. 2006 Dec 3;551(1-3):143-51. Epub 2006 Sep 8. [PubMed:17027748 ]