Human Metabolome Database Version 3.5

Showing metabocard for 3-Methoxy-4-hydroxyphenylglycolaldehyde (HMDB04061)

Record Information
Version 3.5
Creation Date 2006-08-13 04:08:18 -0600
Update Date 2013-05-29 13:39:30 -0600
HMDB ID HMDB04061
Secondary Accession Numbers
  • HMDB06776
Metabolite Identification
Common Name 3-Methoxy-4-hydroxyphenylglycolaldehyde
Description 3-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 Link_out, 9706478 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C9H10O4
Average Molecular Weight 182.1733
Monoisotopic Molecular Weight 182.057908808
IUPAC Name 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
Traditional IUPAC Name 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
CAS Registry Number 17592-23-3
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 Key VISAJVAPYPFKCL-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class Methoxyphenols and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Phenylacetaldehydes
  • a small molecule(Cyc)
Substituents
  • Aldehyde
  • Alkyl Aryl Ether
  • Anisole
  • Benzyl Alcohol Derivative
  • Secondary Alcohol
Direct Parent Methoxyphenols and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 0.517 Not Available
Predicted Properties
Property Value Source
Water Solubility 5.13 g/L ALOGPS
LogP 0.49 ALOGPS
LogP 0.28 ChemAxon
LogS -1.55 ALOGPS
pKa (strongest acidic) 9.9 ChemAxon
pKa (strongest basic) -3.8 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 66.76 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 46.22 ChemAxon
Polarizability 17.67 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Tyrosine Metabolism SMP00006 map00350 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023294
KNApSAcK ID Not Available
Chemspider ID 389601 Link_out
KEGG Compound ID C05583 Link_out
BioCyc ID Not Available
BiGG ID 46069 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB04061 Link_out
Metagene Link HMDB04061 Link_out
METLIN ID Not Available
PubChem Compound 440729 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not 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 Link_out
  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 Link_out

Enzymes
Name: Amine oxidase [flavin-containing] B
Reactions:
Normetanephrine + Water + Oxygen unknown 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxide details
Metanephrine + Water + Oxygen unknown 3-Methoxy-4-hydroxyphenylglycolaldehyde + Hydrogen peroxide + Methylamine details
Gene Name: MAOB
Uniprot ID: P27338 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Amine oxidase [flavin-containing] A
Reactions:
Normetanephrine + Water + Oxygen unknown 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxide details
Metanephrine + Water + Oxygen unknown 3-Methoxy-4-hydroxyphenylglycolaldehyde + Hydrogen peroxide + Methylamine details
Gene Name: MAOA
Uniprot ID: P21397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase, dimeric NADP-preferring
Reactions:
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water unknown Vanillylmandelic acid + NADH + Hydrogen Ion details
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water unknown Vanillylmandelic acid + NADPH + Hydrogen Ion details
Gene Name: ALDH3A1
Uniprot ID: P30838 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase family 1 member A3
Reactions:
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water unknown Vanillylmandelic acid + NADH + Hydrogen Ion details
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water unknown Vanillylmandelic acid + NADPH + Hydrogen Ion details
Gene Name: ALDH1A3
Uniprot ID: P47895 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase family 3 member B2
Reactions:
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water unknown Vanillylmandelic acid + NADH + Hydrogen Ion details
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water unknown Vanillylmandelic acid + NADPH + Hydrogen Ion details
Gene Name: ALDH3B2
Uniprot ID: P48448 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase family 3 member B1
Reactions:
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water unknown Vanillylmandelic acid + NADH + Hydrogen Ion details
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water unknown Vanillylmandelic acid + NADPH + Hydrogen Ion details
Gene Name: ALDH3B1
Uniprot ID: P43353 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA