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

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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
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-004i-0942000000-54f714e694a7c3daeaf4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0931000000-c4bb79d921fb42cf1b40View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9310000000-9490bd0ec921894341f4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-004i-0952000000-d45a1420d6ae61cb9169View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0942000000-54f714e694a7c3daeaf4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0931000000-c4bb79d921fb42cf1b40View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9310000000-9490bd0ec921894341f4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-0952000000-d45a1420d6ae61cb9169View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0931000000-3fab9c521f7f85372b94View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3900000000-9badffe195f5e0ba98e0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-4093000000-178e6eeb94df071e6c15View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0900000000-709dd9faccdbbb3dc088View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9100000000-cf69597350b36ab34199View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200000000-298c198dac69afd9b0a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-0900000000-ace1596cdfcf99646e9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-0900000000-e7f718ad00bdba667583View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-1900000000-d8334a99b44e227f0c59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-01b9-1900000000-72071b19a4bfa3da409dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-3e7377f36ca2547f4885View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-2900000000-60e1fc55d54131c2923eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fi0-9400000000-c63542b296bac95866e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-a59d2cab0d3d859760a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-1900000000-6f630370c11294562cb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9800000000-a45be46f3b52664dd4d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-a59d2cab0d3d859760a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-1900000000-6f630370c11294562cb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9800000000-a45be46f3b52664dd4d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-aec26fe78ab78ddd4021View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dj-2900000000-e59402b8b36f408fbe1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r6-9400000000-f36bad25ade880ae2e1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-579796710abc38249c3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0900000000-22f8a4f4efd0f10804b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zmi-9700000000-42b3de6bccbc10ad7b48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-579796710abc38249c3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0900000000-22f8a4f4efd0f10804b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zmi-9700000000-42b3de6bccbc10ad7b48View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
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