| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-08-12 22:52:53 -0600 |
| Update Date |
2013-02-08 17:12:45 -0700 |
| HMDB ID |
HMDB03791 |
| Secondary Accession Numbers |
|
| 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  , 14697885 , 11164826 , 16956664 . |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 3,4-Dihydroxy-Benzeneacetaldehyde
- 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 |
|
| 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 |
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| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
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| Biological Properties |
|---|
| Cellular Locations |
Not Available
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| Biofluid Locations |
Not Available
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| Tissue Location |
Not Available
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| Pathways |
|
| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank 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 |
| KEGG Compound ID |
C04043 |
| BioCyc ID |
Not Available |
| BiGG ID |
43022 |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB03791 |
| Metagene Link |
HMDB03791 |
| METLIN ID |
Not Available |
| PubChem Compound |
119219 |
| PDB ID |
Not Available |
| ChEBI ID |
27978 |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available
|
