Showing metabocard for 3,4-Dihydroxymandelic acid (BMDB0001866)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:48:23 UTC
Update Date2020-05-21 16:27:05 UTC
BMDB IDBMDB0001866
Secondary Accession Numbers
  • BMDB01866
Metabolite Identification
Common Name3,4-Dihydroxymandelic acid
Description3,4-3,4-3,4-dihydroxymandelic acid, also known as 3,4-dihydroxymandelic acid or 3,4-dihydroxymandelic acid, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-3,4-3,4-dihydroxymandelic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-3,4-3,4-dihydroxymandelic acid exists in all living organisms, ranging from bacteria to humans. 3,4-3,4-3,4-dihydroxymandelic acid participates in a number of enzymatic reactions, within cattle. In particular, 3,4-3,4-3,4-dihydroxymandelic acid can be biosynthesized from 3,4-dihydroxymandelaldehyde; which is mediated by the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In addition, 3,4-3,4-3,4-dihydroxymandelic acid and guaiacol can be converted into vanillylmandelic acid and pyrocatechol through the action of the enzyme catechol O-methyltransferase. In cattle, 3,4-3,4-dihydroxymandelic acid is involved in the metabolic pathway called the tyrosine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3,4-Dihydroxyphenyl)(hydroxy)acetic acidChEBI
3,4-DihydroxymandelateChEBI
3,4-Dihydroxyphenylglycolic acidChEBI
Dihydroxymandelic acidChEBI
DOMAChEBI
(3,4-Dihydroxyphenyl)(hydroxy)acetateGenerator
3,4-DihydroxyphenylglycolateGenerator
DihydroxymandelateGenerator
3,4 DihydroxymandelateHMDB
3,4 Dihydroxymandelic acidHMDB
3,4-Dihydroxymandelic acid, (S)-isomerHMDB
3,4-Dihydroxymandelic acid, ion(1-)HMDB
3,4-Dihydroxymandelic acid, monosodium saltHMDB
DHMAHMDB
3,4-Dihydroxymandelic acid, (+-)-isomerHMDB
Chemical FormulaC8H8O5
Average Molecular Weight184.1461
Monoisotopic Molecular Weight184.037173366
IUPAC Name2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid
Traditional Namedihydroxymandelic acid
CAS Registry Number775-01-9
SMILES
OC(C(O)=O)C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)
InChI KeyRGHMISIYKIHAJW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.72ALOGPS
logP0.29ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.98ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.67 m³·mol⁻¹ChemAxon
Polarizability16.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001866
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030383
KNApSAcK IDNot Available
Chemspider ID77371
KEGG Compound IDC05580
BioCyc IDCPD-11879
BiGG ID46062
Wikipedia Link3,4-Dihydroxymandelic_acid
METLIN ID696
PubChem Compound85782
PDB IDNot Available
ChEBI ID27637
References
Synthesis ReferenceJoray, Marcel; Breuninger, Manfred. Process for the preparation of phenolic compounds. PCT Int. Appl. (2007), 15pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Catechol O-methyltransferase
General function:
Involved in catechol O-methyltransferase activity
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol (By similarity).
Gene Name:
COMT
Uniprot ID:
A7MBI7
Molecular weight:
30485.0
Reactions
3,4-Dihydroxymandelic acid + Guaiacol → Vanillylmandelic acid + Pyrocatecholdetails