Showing metabocard for 3,4-Dihydroxybenzeneacetic acid (BMDB0001336)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:44:19 UTC
Update Date2020-05-21 16:27:05 UTC
BMDB IDBMDB0001336
Secondary Accession Numbers
  • BMDB01336
Metabolite Identification
Common Name3,4-Dihydroxybenzeneacetic acid
Description3,4-Dihydroxybenzeneacetic acid, also known as 3,4-dihydroxybenzeneacetic acid or 3,4-dihydroxybenzeneacetic acid, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-Dihydroxybenzeneacetic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 3,4-Dihydroxybenzeneacetic acid exists in all living organisms, ranging from bacteria to humans. 3,4-Dihydroxybenzeneacetic acid participates in a number of enzymatic reactions, within cattle. In particular, 3,4-Dihydroxybenzeneacetic acid can be biosynthesized from 3,4-dihydroxyphenylacetaldehyde; which is catalyzed by the enzyme 3,4-dihydroxyphenylacetaldehyde. In addition, 3,4-Dihydroxybenzeneacetic acid and guaiacol can be converted into homovanillic acid and pyrocatechol; which is mediated by the enzyme catechol O-methyltransferase. In cattle, 3,4-dihydroxybenzeneacetic acid is involved in the metabolic pathway called the tyrosine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(3,4-DIHYDROXYPHENYL)acetIC ACIDChEBI
3,4-Dihydroxyphenyl acetic acidChEBI
3,4-Dihydroxyphenylacetic acidChEBI
Dopacetic acidChEBI
HomoprotocatechuateKegg
2-(3,4-DIHYDROXYPHENYL)acetateGenerator
3,4-Dihydroxyphenyl acetateGenerator
3,4-DihydroxyphenylacetateGenerator
DopacetateGenerator
3,4-DihydroxybenzeneacetateGenerator
3,4 Dihydroxyphenylacetic acidHMDB
3,4-Dihydroxyphenylacetic acid, monosodium saltHMDB
(3,4-Dihydroxyphenyl)-acetic acidHMDB
(3,4-Dihydroxyphenyl)acetateHMDB
(3,4-Dihydroxyphenyl)acetic acidHMDB
3,4-DHPOPHMDB
3,4-Dihydroxy-benzeneacetic acidHMDB
3,4-Dihydroxy-phenylacetic acidHMDB
DHYHMDB
DihydroxyphenylacetateHMDB
Dihydroxyphenylacetic acidHMDB
HAAHMDB
Homogentisic acidHMDB
3',4'-Dihydroxyphenylacetic acidHMDB
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-(3,4-dihydroxyphenyl)acetic acid
Traditional Name3,4 dihydroxyphenylacetic acid
CAS Registry Number102-32-9
SMILES
OC(=O)CC1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
InChI KeyCFFZDZCDUFSOFZ-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
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point168 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4 mg/mLNot Available
LogP0.98SANGSTER (1994)
Predicted Properties
PropertyValueSource
logP0.93ALOGPS
logP1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.33 m³·mol⁻¹ChemAxon
Polarizability15.71 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
  • Brain
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001336
DrugBank IDDB01702
Phenol Explorer Compound ID572
FooDB IDFDB000316
KNApSAcK IDC00040996
Chemspider ID532
KEGG Compound IDC01161
BioCyc IDCPD-782
BiGG ID36946
Wikipedia LinkDOPAC
METLIN ID6170
PubChem Compound547
PDB IDNot Available
ChEBI ID41941
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-Dihydroxybenzeneacetic acid + Guaiacol → Homovanillic acid + Pyrocatecholdetails