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
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).
DBLinks
- CAS Registry Number: 13023-73-9
- PubChem CID: 151725
- ChEBI: 27852
- HMDB: HMDB0006242
- LipidMaps:
- KEGG: C05577
- BioCyc:
- NCBI MeSH: 3,4-dihydroxyphenylglycolaldehyde
- Wikipedia:
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
- WishartLab ClassyFire: [Phenylacetaldehydes] Phenylacetaldehydes
- RefMet: [Cinnamic acids] Cinnamic acids
- ChEBI: [CHEBI:27852] 3,4-dihydroxymandelaldehyde
- Coconut NaturalProduct: [Cinnamic acids and derivatives] Cinnamic acids and derivatives
| 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+ |
Taxonomy Source
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 |