Record Information
Version3.6
Creation Date2007-05-22 19:02:18 UTC
Update Date2013-05-29 19:43:14 UTC
HMDB IDHMDB06242
Secondary Accession Numbers
  • HMDB04057
Metabolite Identification
Common Name3,4-Dihydroxymandelaldehyde
Description3,4-Dihydroxymandelaldehyde is the monoamine oxidase (MAO) aldehyde metabolite of both norepinephrine and epinephrine. 3,4- dihydroxymandelaldehyde generates a free radical and activates mitochondrial permeability transition, a mechanism implicated in neuron death. There is an increasing body of evidence suggesting that these compounds are neurotoxic, and it has been recently hypothesized that neurodegenerative disorders may be associated with increased levels of this biogenic aldehyde. It is possible to speculate that reduced detoxification of 3,4- dihydroxymandelaldehyde from impaired or deficient aldehyde dehydrogenase function may be a contributing factor in the suggested neurotoxicity of these compounds. Aldehyde dehydrogenases are a group of NAD(P)+ -dependent enzymes that catalyze the oxidation of aldehydes, such as those derived from catecholamines, to their corresponding carboxylic acids. To date, 19 aldehyde dehydrogenase genes have been identified in the human genome. Mutations in these genes and subsequent inborn errors in aldehyde metabolism are the molecular basis of several diseases. Several pharmaceutical agents and environmental toxins are also known to disrupt or inhibit aldehyde dehydrogenase function. (PMID: 17379813 , 14697885 , 11164826 ).
Structure
Thumb
Synonyms
  1. 3,4-Dihydroxyphenylglycolaldehyde
  2. 3,4-Dihydroxyphenylglycolic aldehyde
  3. a,3,4-Trihydroxy-Benzeneacetaldehyde
  4. alpha,3,4-Trihydroxy-Benzeneacetaldehyde
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-(3,4-dihydroxyphenyl)-2-hydroxyacetaldehyde
Traditional IUPAC Name2-(3,4-dihydroxyphenyl)-2-hydroxyacetaldehyde
CAS Registry Number13023-73-9
SMILES
OC(C=O)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-4,8,10-12H
InChI KeyYUGMCLJIWGEKCK-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenylacetaldehydes
Sub ClassN/A
Other Descriptors
  • Organic Compounds
  • a small molecule(Cyc)
  • aldehyde(ChEBI)
  • catechols(ChEBI)
Substituents
  • 1,2 Diphenol
  • Aldehyde
  • Benzyl Alcohol Derivative
  • Phenol
  • Phenol Derivative
  • Secondary Alcohol
Direct ParentPhenylacetaldehydes
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 solubility11 g/LALOGPS
logP0.2ALOGPS
logP0.13ChemAxon
logS-1.2ALOGPS
pKa (strongest acidic)9.2ChemAxon
pKa (strongest basic)-3.8ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count3ChemAxon
polar surface area77.76ChemAxon
rotatable bond count2ChemAxon
refractivity41.74ChemAxon
polarizability15.68ChemAxon
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 IDFDB023855
KNApSAcK IDNot Available
Chemspider ID133725
KEGG Compound IDC05577
BioCyc IDNot Available
BiGG ID46056
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06242
Metagene LinkHMDB06242
METLIN IDNot Available
PubChem Compound151725
PDB IDNot Available
ChEBI ID27852
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Marchitti SA, Deitrich RA, Vasiliou V: Neurotoxicity and metabolism of the catecholamine-derived 3,4-dihydroxyphenylacetaldehyde and 3,4-dihydroxyphenylglycolaldehyde: the role of aldehyde dehydrogenase. Pharmacol Rev. 2007 Jun;59(2):125-50. Epub 2007 Mar 22. Pubmed: 17379813
  2. Burke WJ, Li SW, Chung HD, Ruggiero DA, Kristal BS, Johnson EM, Lampe P, Kumar VB, Franko M, Williams EA, Zahm DS: Neurotoxicity of MAO metabolites of catecholamine neurotransmitters: role in neurodegenerative diseases. Neurotoxicology. 2004 Jan;25(1-2):101-15. Pubmed: 14697885
  3. Burke WJ, Li SW, Zahm DS, Macarthur H, Kolo LL, Westfall TC, Anwar M, Glickstein SB, Ruggiero DA: Catecholamine monoamine oxidase a metabolite in adrenergic neurons is cytotoxic in vivo. Brain Res. 2001 Feb 9;891(1-2):218-27. Pubmed: 11164826

Enzymes

Gene Name:
MAOB
Uniprot ID:
P27338
Reactions
Norepinephrine + Water + Oxygen unknown 3,4-Dihydroxymandelaldehyde + Ammonia + Hydrogen peroxidedetails
Epinephrine + Water + Oxygen unknown 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxidedetails
Gene Name:
MAOA
Uniprot ID:
P21397
Reactions
Norepinephrine + Water + Oxygen unknown 3,4-Dihydroxymandelaldehyde + Ammonia + Hydrogen peroxidedetails
Epinephrine + Water + Oxygen unknown 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxidedetails
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Reactions
3,4-Dihydroxymandelaldehyde + NAD + Water unknown 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water unknown 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Iondetails
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Reactions
3,4-Dihydroxymandelaldehyde + NAD + Water unknown 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water unknown 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Iondetails
Gene Name:
ADH4
Uniprot ID:
P08319
Reactions
3,4-Dihydroxyphenylglycol + NAD unknown 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Reactions
3,4-Dihydroxymandelaldehyde + NAD + Water unknown 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water unknown 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Iondetails
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Reactions
3,4-Dihydroxymandelaldehyde + NAD + Water unknown 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water unknown 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Iondetails
Gene Name:
ADH5
Uniprot ID:
P11766
Reactions
3,4-Dihydroxyphenylglycol + NAD unknown 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
Gene Name:
ADH1B
Uniprot ID:
P00325
Reactions
3,4-Dihydroxyphenylglycol + NAD unknown 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
Gene Name:
ADH7
Uniprot ID:
P40394
Reactions
3,4-Dihydroxyphenylglycol + NAD unknown 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
Gene Name:
ADH1A
Uniprot ID:
P07327
Reactions
3,4-Dihydroxyphenylglycol + NAD unknown 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
Gene Name:
ADH6
Uniprot ID:
P28332
Reactions
3,4-Dihydroxyphenylglycol + NAD unknown 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
Gene Name:
ADH1C
Uniprot ID:
P00326
Reactions
3,4-Dihydroxyphenylglycol + NAD unknown 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails