Human Metabolome Database Version 3.5

Showing metabocard for Homovanillin (HMDB05175)

Record Information
Version 3.5
Creation Date 2006-10-31 06:02:28 -0700
Update Date 2013-05-29 13:41:52 -0600
HMDB ID HMDB05175
Secondary Accession Numbers None
Metabolite Identification
Common Name Homovanillin
Description 3 -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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C9H10O3
Average Molecular Weight 166.1739
Monoisotopic Molecular Weight 166.062994186
IUPAC Name 2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
Traditional IUPAC Name homovanillin
CAS Registry Number 5703-24-2
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 Key GOQGGGANVKPMNH-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
  • phenylacetaldehydes(ChEBI)
Substituents
  • Aldehyde
  • Alkyl Aryl Ether
  • Anisole
Direct Parent Methoxyphenols and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
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 Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 2.9 g/L ALOGPS
LogP 1.52 ALOGPS
LogP 0.99 ChemAxon
LogS -1.76 ALOGPS
pKa (strongest acidic) 9.94 ChemAxon
pKa (strongest basic) -4.9 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 46.53 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 44.88 ChemAxon
Polarizability 16.81 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
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 FDB023632
KNApSAcK ID Not Available
Chemspider ID 133331 Link_out
KEGG Compound ID C05581 Link_out
BioCyc ID Not Available
BiGG ID 46064 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB05175 Link_out
Metagene Link HMDB05175 Link_out
METLIN ID Not Available
PubChem Compound 151276 Link_out
PDB ID Not Available
ChEBI ID 28111 Link_out
References
Synthesis Reference Harries, 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 Link_out

Enzymes
Name: Amine oxidase [flavin-containing] B
Reactions:
3-Methoxytyramine + Water + Oxygen unknown Homovanillin + Hydrogen peroxide + Ammonia details
Gene Name: MAOB
Uniprot ID: P27338 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Amine oxidase [flavin-containing] A
Reactions:
3-Methoxytyramine + Water + Oxygen unknown Homovanillin + Hydrogen peroxide + Ammonia details
Gene Name: MAOA
Uniprot ID: P21397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase, dimeric NADP-preferring
Reactions:
Homovanillin + NAD + Water unknown Homovanillic acid + NADH + Hydrogen Ion details
Homovanillin + NADP + Water unknown Homovanillic 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:
Homovanillin + NAD + Water unknown Homovanillic acid + NADH + Hydrogen Ion details
Homovanillin + NADP + Water unknown Homovanillic 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:
Homovanillin + NAD + Water unknown Homovanillic acid + NADH + Hydrogen Ion details
Homovanillin + NADP + Water unknown Homovanillic 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:
Homovanillin + NAD + Water unknown Homovanillic acid + NADH + Hydrogen Ion details
Homovanillin + NADP + Water unknown Homovanillic acid + NADPH + Hydrogen Ion details
Gene Name: ALDH3B1
Uniprot ID: P43353 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA