3,4-Dihydroxymandelaldehyde (BioCAD00000003874)

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Metabolite Card

Formula: C8H8O4 (168.0423)
SMILES: OC(C=O)C1=CC(O)=C(O)C=C1

Synonyms [en]

3,4-Dihydroxymandelaldehyde; DOPEGAL; DHPGALD; 3,4-Dihydroxyphenylglycolaldehyde; DHMAL; 3,4-dihydroxyphenylglycolic aldehyde

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

3,4-Dihydroxymandelaldehyde. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000003874). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

3,4-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).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 13023-73-9
  • PubChem: 151725
  • ChEBI: ChEBI:27852
  • HMDB: HMDB0006242
  • HMDB: HMDB06242
  • KEGG: C05577
  • NCBI MeSH: 3,4-dihydroxyphenylglycolaldehyde
  • RefMet: RM0007931
  • Metlin: METLIN_58374
  • Coconut NaturalProduct: CNP0280132.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02532 1.4.3.4 4-[(1R)-2-amino-1-hydroxyethyl]-1,2-benzenediol:oxygen oxidoreductase(deaminating)(flavin-containing)
KEGG:R02919 1.4.3.4 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-1,2-benzenediol:oxygen oxidoreductase(deaminating)(flavin-containing)
KEGG:R04880 1.1.1.1 3,4-dihydroxyphenylethyleneglycol:NAD+ oxidoreductase
KEGG:R04882 1.2.1.5 3,4-dihydroxymandelaldehyde:NAD+ oxidoreductase
KEGG:R04883 1.2.1.5 3,4-dihydroxymandelaldehyde:NADP+ oxidoreductase
Rhea:RHEA:31148 3,4-dihydroxyphenylethyleneglycol + NAD+ => 3,4-dihydroxymandelaldehyde + NADH + H+
Rhea:RHEA:31149 3,4-dihydroxymandelaldehyde + NADH + H+ => 3,4-dihydroxyphenylethyleneglycol + NAD+
Rhea:RHEA:31150 3,4-dihydroxyphenylethyleneglycol + NAD+ <=> 3,4-dihydroxymandelaldehyde + NADH + H+
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Organism Source

Taxonomy Source

  1. Mus musculus [ncbi taxid: 10090]

Pathway Synthetic

pathway id name
BioCyc:THAPS_PWY-6342 noradrenaline and adrenaline degradation
Reactome:R-BTA-112310 Neurotransmitter release cycle
Reactome:R-CFA-112315 Transmission across Chemical Synapses
Reactome:R-DRE-112315 Transmission across Chemical Synapses
Reactome:R-DDI-181430 Norepinephrine Neurotransmitter Release Cycle
Reactome:R-GGA-181430 Norepinephrine Neurotransmitter Release Cycle
Reactome:R-HSA-112315 Transmission across Chemical Synapses
Reactome:R-MMU-181430 Norepinephrine Neurotransmitter Release Cycle
Reactome:R-RNO-112316 Neuronal System
Reactome:R-SSC-112315 Transmission across Chemical Synapses
Reactome:R-XTR-112310 Neurotransmitter release cycle
Reactome:R-BTA-112316 Neuronal System
Reactome:R-CFA-181430 Norepinephrine Neurotransmitter Release Cycle
Reactome:R-DRE-181430 Norepinephrine Neurotransmitter Release Cycle
Reactome:R-DDI-112310 Neurotransmitter release cycle
Reactome:R-GGA-112310 Neurotransmitter release cycle
Reactome:R-HSA-181430 Norepinephrine Neurotransmitter Release Cycle
Reactome:R-MMU-112310 Neurotransmitter release cycle
Reactome:R-RNO-112315 Transmission across Chemical Synapses
Reactome:R-SSC-181430 Norepinephrine Neurotransmitter Release Cycle
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