P. aeruginosa Metabolome Database: 3,4-dihydroxyphenylglycolaldehyde (PAMDB120522)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB120522

Identification

Name:

3,4-dihydroxyphenylglycolaldehyde

Description:

An aldehyde consisting of phenylacetaldehyde having three hydroxy substituents located at the α-, 3- and 4-positions

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

3,4-dihydroxymandelaldehyde
3,4-dihydroxymandelic aldehyde
3,4-Dihydroxyphenylglycolaldehyde
3,4-dihydroxyphenylglycolic aldehyde
α,3,4-trihydroxybenzeneacetaldehyde
α,3,4-trihydroxyphenylacetaldehyde
DHMAL
DHPGALD
DOPEGAL

Chemical Formula:

C₈H₈O₄

Average Molecular Weight:

168.149

Monoisotopic Molecular Weight:

168.04225

InChI Key:

YUGMCLJIWGEKCK-QMMMGPOBSA-N

InChI:

InChI=1S/C8H8O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-4,8,10-12H/t8-/m0/s1

CAS number:

13023-73-9

IUPAC Name:

2-(3,4-dihydroxyphenyl)-2-hydroxyacetaldehyde

Traditional IUPAC Name:

dhmal

SMILES:

C(=O)C(O)C1(C=CC(O)=C(O)C=1)

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of chemical entities known as phenylacetaldehydes. These are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Benzenoids

Sub Class

Benzene and substituted derivatives

Direct Parent

Phenylacetaldehydes

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:27852 )
aldehyde (CHEBI:27852 )
a small molecule (DIHYDROXYPHENYLGLYCOLALDEHYDE )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	11.0 mg/mL	ALOGPS
logP	0.2	ALOGPS
logP	0.13	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	9.2	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.74 m³·mol^-1	ChemAxon
Polarizability	15.68 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

3,4-dihydroxyphenylglycol + NAD+ → 3,4-dihydroxyphenylglycolaldehyde + NADH + Hydrogen ion

Pathways:

Tyrosine Metabolism pae00350

Spectra

Spectra:

Not Available

References

References:

Narayanan J, Hayakawa Y, Fan J, Kirk KL (2003)Convenient syntheses of biogenic aldehydes, 3,4-dihydroxyphenylacetaldehyde and 3,4-dihydroxyphenylglycolaldehyde. Bioorganic chemistry 31, Pubmed: 12729575
Burke WJ, Schmitt CA, Gillespie KN, Li SW (1996)Norepinephrine transmitter metabolite is a selective cell death messenger in differentiated rat pheochromocytoma cells. Brain research 722, Pubmed: 8813375
Kawamura M, Eisenhofer G, Kopin IJ, Kador PF, Lee YS, Tsai JY, Fujisawa S, Lizak MJ, Sinz A, Sato S (1999)Aldose reductase, a key enzyme in the oxidative deamination of norepinephrine in rats. Biochemical pharmacology 58, Pubmed: 10424772
Dina OA, Khasar SG, Alessandri-Haber N, Bogen O, Chen X, Green PG, Reichling DB, Messing RO, Levine JD (2008)Neurotoxic catecholamine metabolite in nociceptors contributes to painful peripheral neuropathy. The European journal of neuroscience 28, Pubmed: 18783367
Li SW, Lin TS, Minteer S, Burke WJ (2001)3,4-Dihydroxyphenylacetaldehyde and hydrogen peroxide generate a hydroxyl radical: possible role in Parkinson's disease pathogenesis. Brain research. Molecular brain research 93, Pubmed: 11532332
Burke WJ, Schmitt CA, Miller C, Li SW (1997)Norepinephrine transmitter metabolite induces apoptosis in differentiated rat pheochromocytoma cells. Brain research 760, Pubmed: 9237550
Burke WJ, Kristal BS, Yu BP, Li SW, Lin TS (1998)Norepinephrine transmitter metabolite generates free radicals and activates mitochondrial permeability transition: a mechanism for DOPEGAL-induced apoptosis. Brain research 787, Pubmed: 9518674
Burke WJ, Li SW, Schmitt CA, Xia P, Chung HD, Gillespie KN (1999)Accumulation of 3,4-dihydroxyphenylglycolaldehyde, the neurotoxic monoamine oxidase A metabolite of norepinephrine, in locus ceruleus cell bodies in Alzheimer's disease: mechanism of neuron death. Brain research 816, Pubmed: 9878889
Burke WJ, Li SW, Chung HD, Ruggiero DA, Kristal BS, Johnson EM, Lampe P, Kumar VB, Franko M, Williams EA, Zahm DS (2004)Neurotoxicity of MAO metabolites of catecholamine neurotransmitters: role in neurodegenerative diseases. Neurotoxicology 25, Pubmed: 14697885

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
METABOLIGHTS	MTBLC27852
HMDB	HMDB06242
CHEMSPIDER	133725
CHEBI	27852
PUBCHEM	151725
LIGAND-CPD	C05577

3,4-dihydroxyphenylglycolaldehyde (PAMDB120522)

Structure for 3,4-dihydroxyphenylglycolaldehyde (PAMDB120522)