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Record Information
Version3.6
Creation Date2006-10-31 13:02:28 UTC
Update Date2013-05-29 19:41:52 UTC
HMDB IDHMDB05175
Secondary Accession NumbersNone
Metabolite Identification
Common NameHomovanillin
Description3 -Methoxy-4-hydroxyphenylacetaldehyde is an intermediary aldehyde of dopamine metabolism, metabolized by the class I human liver alcohol dehydrogenases (ADHs). ADH catalyzes both ethanol and acetaldehyde, and the dopamine intermediates compete for the same site of ADH, a basis for the ethanol-induced in vivo alterations of dopamine metabolism. (PMID 2432930 ).
Structure
Thumb
Synonyms
  1. (4-Hydroxy-3-methoxyphenyl)acetaldehyde
  2. 2-(4-Hydroxy-3-methoxyphenyl) Ethanal
  3. 4-Hydroxy-3-methoxy-Benzeneacetaldehyde
  4. 4-Hydroxy-3-methoxybenzeneacetaldehyde
  5. HMPAL
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
Traditional IUPAC Namehomovanillin
CAS Registry Number5703-24-2
SMILES
COC1=C(O)C=CC(CC=O)=C1
InChI Identifier
InChI=1S/C9H10O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,5-6,11H,4H2,1H3
InChI KeyGOQGGGANVKPMNH-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenols and Derivatives
Sub ClassMethoxyphenols and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Phenylacetaldehydes
  • phenylacetaldehydes(ChEBI)
Substituents
  • Aldehyde
  • Alkyl Aryl Ether
  • Anisole
Direct ParentMethoxyphenols and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 solubility2.9 g/LALOGPS
logP1.52ALOGPS
logP0.99ChemAxon
logS-1.8ALOGPS
pKa (strongest acidic)9.94ChemAxon
pKa (strongest basic)-4.9ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area46.53ChemAxon
rotatable bond count3ChemAxon
refractivity44.88ChemAxon
polarizability16.81ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
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 IDFDB023632
KNApSAcK IDNot Available
Chemspider ID133331
KEGG Compound IDC05581
BioCyc IDNot Available
BiGG ID46064
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05175
Metagene LinkHMDB05175
METLIN IDNot Available
PubChem Compound151276
PDB IDNot Available
ChEBI ID28111
References
Synthesis ReferenceHarries, C. Homovanillin. Berichte der Deutschen Chemischen Gesellschaft (1915), 48 868-9. CODEN: BDCGAS ISSN:0365-9496. CAN 9:13972 AN 1915:13972
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mardh G, Vallee BL: Human class I alcohol dehydrogenases catalyze the interconversion of alcohols and aldehydes in the metabolism of dopamine. Biochemistry. 1986 Nov 18;25(23):7279-82. Pubmed: 2432930

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
3-Methoxytyramine + Water + Oxygen → Homovanillin + Hydrogen peroxide + Ammoniadetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
3-Methoxytyramine + Water + Oxygen → Homovanillin + Hydrogen peroxide + Ammoniadetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
Homovanillin + NAD + Water → Homovanillic acid + NADH + Hydrogen Iondetails
Homovanillin + NADP + Water → Homovanillic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
Homovanillin + NAD + Water → Homovanillic acid + NADH + Hydrogen Iondetails
Homovanillin + NADP + Water → Homovanillic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
Homovanillin + NAD + Water → Homovanillic acid + NADH + Hydrogen Iondetails
Homovanillin + NADP + Water → Homovanillic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
Homovanillin + NAD + Water → Homovanillic acid + NADH + Hydrogen Iondetails
Homovanillin + NADP + Water → Homovanillic acid + NADPH + Hydrogen Iondetails