Human Metabolome Database Version 3.5

Showing metabocard for 3,4-Dihydroxyphenylacetaldehyde (HMDB03791)

Record Information
Version 3.5
Creation Date 2006-08-12 22:52:53 -0600
Update Date 2013-05-29 13:38:56 -0600
HMDB ID HMDB03791
Secondary Accession Numbers
  • HMDB06256
  • HMDB06778
Metabolite Identification
Common Name 3,4-Dihydroxyphenylacetaldehyde
Description 3,4-Dihydroxyphenylacetaldehyde (DOPAL) is a metabolite of the monoamine oxidase-catalyzed oxidative deamination of dopamine. Aldehydes are highly reactive molecules formed during the biotransformation of numerous endogenous and exogenous compounds, including biogenic amines. DOPAL 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 (i.e.: 4-hydroxy-2-nonenal) are also known to disrupt or inhibit aldehyde dehydrogenase function. (PMID: 17379813 Link_out, 14697885 Link_out, 11164826 Link_out, 16956664 Link_out.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3,4-Dihydroxy-Benzeneacetaldehyde
  2. Protocatechuatealdehyde
Chemical Formula C8H8O3
Average Molecular Weight 152.1473
Monoisotopic Molecular Weight 152.047344122
IUPAC Name 2-(3,4-dihydroxyphenyl)acetaldehyde
Traditional IUPAC Name 2-(3,4-dihydroxyphenyl)acetaldehyde
CAS Registry Number 5707-55-1
SMILES OC1=C(O)C=C(CC=O)C=C1
InChI Identifier InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2
InChI Key IADQVXRMSNIUEL-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenylacetaldehydes
Sub Class N/A
Other Descriptors
  • Organic Compounds
  • a small molecule(Cyc)
  • catechols(ChEBI)
  • phenylacetaldehydes(ChEBI)
Substituents
  • 1,2 Diphenol
  • Aldehyde
  • Phenol
  • Phenol Derivative
Direct Parent Phenylacetaldehydes
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 1.005 Not Available
Predicted Properties
Property Value Source
Water Solubility 8.72 g/L ALOGPS
LogP 1.15 ALOGPS
LogP 0.85 ChemAxon
LogS -1.24 ALOGPS
pKa (strongest acidic) 9.27 ChemAxon
pKa (strongest basic) -6.3 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 40.4 ChemAxon
Polarizability 14.78 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 FDB023227
KNApSAcK ID Not Available
Chemspider ID 106504 Link_out
KEGG Compound ID C04043 Link_out
BioCyc ID Not Available
BiGG ID 43022 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB03791 Link_out
Metagene Link HMDB03791 Link_out
METLIN ID Not Available
PubChem Compound 119219 Link_out
PDB ID Not Available
ChEBI ID 27978 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  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 Link_out
  4. Florang VR, Rees JN, Brogden NK, Anderson DG, Hurley TD, Doorn JA: Inhibition of the oxidative metabolism of 3,4-dihydroxyphenylacetaldehyde, a reactive intermediate of dopamine metabolism, by 4-hydroxy-2-nonenal. Neurotoxicology. 2007 Jan;28(1):76-82. Epub 2006 Aug 1. Pubmed: 16956664 Link_out

Enzymes
Name: Amine oxidase [flavin-containing] B
Reactions:
Dopamine + Water + Oxygen unknown 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide details
Gene Name: MAOB
Uniprot ID: P27338 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Amine oxidase [flavin-containing] A
Reactions:
Dopamine + Water + Oxygen unknown 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide details
Gene Name: MAOA
Uniprot ID: P21397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase, dimeric NADP-preferring
Reactions:
3,4-Dihydroxyphenylacetaldehyde + NAD + Water unknown 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Ion details
3,4-Dihydroxyphenylacetaldehyde + NADP + Water unknown 3,4-Dihydroxybenzeneacetic 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:
3,4-Dihydroxyphenylacetaldehyde + NAD + Water unknown 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Ion details
3,4-Dihydroxyphenylacetaldehyde + NADP + Water unknown 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Ion details
Gene Name: ALDH1A3
Uniprot ID: P47895 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Amiloride-sensitive amine oxidase [copper-containing]
Reactions: Not Available
Gene Name: ABP1
Uniprot ID: P19801 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Membrane primary amine oxidase
Reactions:
Dopamine + Water + Oxygen unknown 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide details
Gene Name: AOC3
Uniprot ID: Q16853 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Retina-specific copper amine oxidase
Reactions:
Dopamine + Water + Oxygen unknown 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide details
Gene Name: AOC2
Uniprot ID: O75106 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase family 3 member B2
Reactions:
3,4-Dihydroxyphenylacetaldehyde + NAD + Water unknown 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Ion details
3,4-Dihydroxyphenylacetaldehyde + NADP + Water unknown 3,4-Dihydroxybenzeneacetic 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:
3,4-Dihydroxyphenylacetaldehyde + NAD + Water unknown 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Ion details
3,4-Dihydroxyphenylacetaldehyde + NADP + Water unknown 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Ion details
Gene Name: ALDH3B1
Uniprot ID: P43353 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA