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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 19:02:18 UTC
Update Date2021-09-14 15:00:11 UTC
HMDB IDHMDB0006242
Secondary Accession Numbers
  • HMDB0004057
  • HMDB04057
  • HMDB06242
Metabolite Identification
Common Name3,4-Dihydroxymandelaldehyde
Description3,4-Dihydroxymandelaldehyde, also known as DHMAL or DHPGALD, belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. 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. 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. 3,4-Dihydroxymandelaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-Dihydroxymandelaldehyde exists in all living organisms, ranging from bacteria to humans. Within humans, 3,4-dihydroxymandelaldehyde participates in a number of enzymatic reactions. In particular, 3,4-dihydroxymandelaldehyde can be biosynthesized from norepinephrine through the action of the enzyme amine oxidase [flavin-containing] a. In addition, 3,4-dihydroxymandelaldehyde and methylamine can be biosynthesized from epinephrine through its interaction with the enzyme amine oxidase [flavin-containing] a. In humans, 3,4-dihydroxymandelaldehyde is involved in the metabolic disorder called tyrosinemia type I. Outside of the human body, 3,4-Dihydroxymandelaldehyde has been detected, but not quantified in, several different foods, such as wild carrots, kohlrabis, angelica, sunburst squash (pattypan squash), and peachs. This could make 3,4-dihydroxymandelaldehyde a potential biomarker for the consumption of these foods. To date, 19 aldehyde dehydrogenase genes have been identified in the human genome. Several pharmaceutical agents and environmental toxins are also known to disrupt or inhibit aldehyde dehydrogenase function. Mutations in these genes and subsequent inborn errors in aldehyde metabolism are the molecular basis of several diseases. 3,4- dihydroxymandelaldehyde generates a free radical and activates mitochondrial permeability transition, a mechanism implicated in neuron death. 3,4-Dihydroxymandelaldehyde is the monoamine oxidase (MAO) aldehyde metabolite of both norepinephrine and epinephrine.
Structure
Data?1582752376
Synonyms
ValueSource
3,4-Dihydroxymandelic aldehydeChEBI
3,4-DihydroxyphenylglycolaldehydeChEBI
3,4-Dihydroxyphenylglycolic aldehydeChEBI
alpha,3,4-TrihydroxybenzeneacetaldehydeChEBI
alpha,3,4-TrihydroxyphenylacetaldehydeChEBI
DHMALChEBI
DHPGALDChEBI
DOPEGALChEBI
a,3,4-TrihydroxybenzeneacetaldehydeGenerator
Α,3,4-trihydroxybenzeneacetaldehydeGenerator
a,3,4-TrihydroxyphenylacetaldehydeGenerator
Α,3,4-trihydroxyphenylacetaldehydeGenerator
a,3,4-Trihydroxy-benzeneacetaldehydeHMDB
alpha,3,4-Trihydroxy-benzeneacetaldehydeHMDB
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-(3,4-dihydroxyphenyl)-2-hydroxyacetaldehyde
Traditional Namedhmal
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
Description Belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetaldehydes
Direct ParentPhenylacetaldehydes
Alternative Parents
Substituents
  • Phenylacetaldehyde
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility11 g/LALOGPS
logP10(0.2) g/LALOGPS
logP10(0.13) g/LChemAxon
logS10(-1.2) g/LALOGPS
pKa (Strongest Acidic)9.2ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.74 m³·mol⁻¹ChemAxon
Polarizability15.68 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.14931661259
DarkChem[M-H]-132.88331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-DihydroxymandelaldehydeOC(C=O)C1=CC(O)=C(O)C=C13267.4Standard polar33892256
3,4-DihydroxymandelaldehydeOC(C=O)C1=CC(O)=C(O)C=C11599.0Standard non polar33892256
3,4-DihydroxymandelaldehydeOC(C=O)C1=CC(O)=C(O)C=C11696.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Dihydroxymandelaldehyde,1TMS,isomer #1C[Si](C)(C)OC(C=O)C1=CC=C(O)C(O)=C11812.4Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,1TMS,isomer #2C[Si](C)(C)OC1=CC(C(O)C=O)=CC=C1O1745.4Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(C(O)C=O)C=C1O1770.2Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,1TMS,isomer #4C[Si](C)(C)OC=C(O)C1=CC=C(O)C(O)=C12017.5Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(C(C=O)O[Si](C)(C)C)C=C1O1806.9Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,2TMS,isomer #2C[Si](C)(C)OC1=CC(C(C=O)O[Si](C)(C)C)=CC=C1O1789.7Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,2TMS,isomer #3C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O)C(O)=C12087.8Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,2TMS,isomer #4C[Si](C)(C)OC1=CC=C(C(O)C=O)C=C1O[Si](C)(C)C1778.6Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,2TMS,isomer #5C[Si](C)(C)OC=C(O)C1=CC=C(O)C(O[Si](C)(C)C)=C11944.5Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,2TMS,isomer #6C[Si](C)(C)OC=C(O)C1=CC=C(O[Si](C)(C)C)C(O)=C11969.4Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(C(C=O)O[Si](C)(C)C)C=C1O[Si](C)(C)C1833.3Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,3TMS,isomer #2C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C12034.0Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,3TMS,isomer #3C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C12007.0Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,3TMS,isomer #4C[Si](C)(C)OC=C(O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11983.5Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,4TMS,isomer #1C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12060.3Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,4TMS,isomer #1C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11993.4Standard non polar33892256
3,4-Dihydroxymandelaldehyde,4TMS,isomer #1C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12023.7Standard polar33892256
3,4-Dihydroxymandelaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C=O)C1=CC=C(O)C(O)=C12055.7Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(C(O)C=O)=CC=C1O1985.0Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)C=O)C=C1O2009.6Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC=C(O)C1=CC=C(O)C(O)=C12284.1Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C(C=O)O[Si](C)(C)C(C)(C)C)C=C1O2277.0Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(C(C=O)O[Si](C)(C)C(C)(C)C)=CC=C1O2268.7Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C12572.1Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)C=O)C=C1O[Si](C)(C)C(C)(C)C2264.6Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC=C(O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12476.1Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC=C(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12519.4Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C(C=O)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2525.3Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12773.6Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12752.8Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC=C(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12723.1Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12960.1Semi standard non polar33892256
3,4-Dihydroxymandelaldehyde,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12790.0Standard non polar33892256
3,4-Dihydroxymandelaldehyde,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12462.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxymandelaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-06ri-1900000000-d14339278a251a7d9df12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxymandelaldehyde GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-7079000000-441c5f66bee2b8f14be72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxymandelaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxymandelaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 10V, Positive-QTOFsplash10-014i-0900000000-01c8f9ca75c86beb71182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 20V, Positive-QTOFsplash10-0gb9-0900000000-30165da526b8042721a92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 40V, Positive-QTOFsplash10-0kn9-9800000000-24ef8505a6b8f892128d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 10V, Negative-QTOFsplash10-014i-0900000000-2ce2cd9a3f1a5d4737b32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 20V, Negative-QTOFsplash10-0aor-0900000000-a9b6cf257bb2c852ffd92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 40V, Negative-QTOFsplash10-0a4i-6900000000-1f2d65b1c1a32c4ea1fd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 10V, Negative-QTOFsplash10-014j-0900000000-876434025a3e5951556f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 20V, Negative-QTOFsplash10-00di-0900000000-667ec91845715350734f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 40V, Negative-QTOFsplash10-052f-9200000000-1663e47bc16a5fa465e42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 10V, Positive-QTOFsplash10-0fki-0900000000-d67f635e503103dc887e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 20V, Positive-QTOFsplash10-0r7i-4900000000-0f535b7035498a1a63032021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 40V, Positive-QTOFsplash10-0ue9-9200000000-344fc9120de4f34191d32021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030386
KNApSAcK IDNot Available
Chemspider ID133725
KEGG Compound IDC05577
BioCyc IDDIHYDROXYPHENYLGLYCOLALDEHYDE
BiGG ID46056
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151725
PDB IDNot Available
ChEBI ID27852
Food Biomarker OntologyNot Available
VMH ID34DHMALD
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
Norepinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Ammonia + Hydrogen peroxidedetails
Epinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
Norepinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Ammonia + Hydrogen peroxidedetails
Epinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH4
Uniprot ID:
P08319
Molecular weight:
40221.335
Reactions
3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular weight:
39723.945
Reactions
3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular weight:
39835.17
Reactions
3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:
ADH7
Uniprot ID:
P40394
Molecular weight:
41480.985
Reactions
3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails

Only showing the first 10 proteins. There are 13 proteins in total.