Record Information
Version3.6
Creation Date2006-08-13 10:08:18 UTC
Update Date2013-05-29 19:39:30 UTC
HMDB IDHMDB04061
Secondary Accession Numbers
  • HMDB06776
Metabolite Identification
Common Name3-Methoxy-4-hydroxyphenylglycolaldehyde
Description3-Methoxy-4-hydroxyphenylglycolaldehyde is the monoamine oxidase (MAO) aldehyde metabolite of metanephrine. Metanephrine is an O-methylated metabolite formed by catechol-O-methyltransferase (COMT) from epinephrine. Catecholamines play an important role in platelet activation and aggregation, epinephrine being the most potent one. Catecholamines are substantially increased during stress, exercise or smoking and could result in clinically important platelet activation if their action was not rapidly regulated. The inhibitory effects of methoxy phenolic derivatives on epinephrine-induced platelet aggregation may possibly be attributed to their free radical scavenging properties. There is substantial evidence to conclude that an internal rapid autoregulation of epinephrine-induced platelet aggregation, caused by its metabolic degradation products, takes place in vivo. (PMID: 11958479 , 9706478 ).
Structure
Thumb
Synonyms
  1. 4-Hydroxy-3-methoxy Mandelaldehyde
  2. 4-Hydroxy-3-methoxymandelaldehyde
  3. 4-Hydroxy-3-methoxyphenylglycolaldehyde
  4. a,4-Dihydroxy-3-methoxy-Benzeneacetaldehyde
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
Traditional IUPAC Name2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
CAS Registry Number17592-23-3
SMILES
COC1=C(O)C=CC(=C1)C(O)C=O
InChI Identifier
InChI=1S/C9H10O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-5,8,11-12H,1H3
InChI KeyVISAJVAPYPFKCL-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenols and Derivatives
Sub ClassMethoxyphenols and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Phenylacetaldehydes
  • a small molecule(Cyc)
Substituents
  • Aldehyde
  • Alkyl Aryl Ether
  • Anisole
  • Benzyl Alcohol Derivative
  • Secondary Alcohol
Direct ParentMethoxyphenols and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.517Not Available
Predicted Properties
PropertyValueSource
water solubility5.13 g/LALOGPS
logP0.49ALOGPS
logP0.28ChemAxon
logS-1.6ALOGPS
pKa (strongest acidic)9.9ChemAxon
pKa (strongest basic)-3.8ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area66.76ChemAxon
rotatable bond count3ChemAxon
refractivity46.22ChemAxon
polarizability17.67ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006map00350
Normal Concentrations
Not Available
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 IDNot Available
FoodDB IDFDB023294
KNApSAcK IDNot Available
Chemspider ID389601
KEGG Compound IDC05583
BioCyc IDNot Available
BiGG ID46069
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04061
Metagene LinkHMDB04061
METLIN IDNot Available
PubChem Compound440729
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kawamura M, Eisenhofer G, Kopin IJ, Kador PF, Lee YS, Fujisawa S, Sato S: Aldose reductase: an aldehyde scavenging enzyme in the intraneuronal metabolism of norepinephrine in human sympathetic ganglia. Auton Neurosci. 2002 Mar 18;96(2):131-9. Pubmed: 11958479
  2. Evangelou AM, Malamas MP, Vezyraki P, Karkabounas SC: Is epinephrine-induced platelet aggregation autoregulated by its metabolic degradation products in vivo? In Vivo. 1998 May-Jun;12(3):321-5. Pubmed: 9706478

Enzymes

Gene Name:
MAOB
Uniprot ID:
P27338
Reactions
Normetanephrine + Water + Oxygen unknown 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxidedetails
Metanephrine + Water + Oxygen unknown 3-Methoxy-4-hydroxyphenylglycolaldehyde + Hydrogen peroxide + Methylaminedetails
Gene Name:
MAOA
Uniprot ID:
P21397
Reactions
Normetanephrine + Water + Oxygen unknown 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxidedetails
Metanephrine + Water + Oxygen unknown 3-Methoxy-4-hydroxyphenylglycolaldehyde + Hydrogen peroxide + Methylaminedetails
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Reactions
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water unknown Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water unknown Vanillylmandelic acid + NADPH + Hydrogen Iondetails
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Reactions
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water unknown Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water unknown Vanillylmandelic acid + NADPH + Hydrogen Iondetails
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Reactions
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water unknown Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water unknown Vanillylmandelic acid + NADPH + Hydrogen Iondetails
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Reactions
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water unknown Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water unknown Vanillylmandelic acid + NADPH + Hydrogen Iondetails