Showing metabocard for Vanylglycol (BMDB0001490)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:46:41 UTC
Update Date2020-05-21 16:27:04 UTC
BMDB IDBMDB0001490
Secondary Accession Numbers
  • BMDB01490
Metabolite Identification
Common NameVanylglycol
DescriptionVanylglycol, also known as MHPG or vanylglycol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Vanylglycol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Vanylglycol and pyrocatechol can be biosynthesized from 3,4-dihydroxyphenylglycol and guaiacol through its interaction with the enzyme catechol O-methyltransferase. In cattle, vanylglycol is involved in the metabolic pathway called the tyrosine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(4-Hydroxy-3-methoxyphenyl)-1,2-ethanediolHMDB
3-Methoxy-4-hydroxyphenethylene glycolHMDB
3-Methoxy-4-hydroxyphenyl glycolHMDB
4-Hydroxy-3-methoxy-b-phenylglycolHMDB
4-Hydroxy-3-methoxy-beta-phenylglycolHMDB
4-Hydroxy-3-methoxyphenyl glycolHMDB
HMPGHMDB
HydroxymethoxyphenylglycolHMDB, MeSH
MethoxyhydroxyphenylglycolHMDB, MeSH
MHPGHMDB, MeSH
MOPEGHMDB, MeSH
4 Hydroxy 3 methoxyphenylethyleneglycolMeSH, HMDB
4 Hydroxy 3 methoxyphenylglycolMeSH, HMDB
4-Hydroxy-3-methoxyphenylethyleneglycolMeSH, HMDB
Methoxyhydroxyphenylglycol, (-)-isomerMeSH, HMDB
4 Hydroxy 3 methoxyphenylethylene glycolMeSH, HMDB
4-Hydroxy-3-methoxyphenylglycolMeSH, HMDB
Methoxyhydroxyphenylglycol, (+)-isomerMeSH, HMDB
4-Hydroxy-3-methoxyphenylethylene glycolMeSH, HMDB
Methoxyhydroxyphenylglycol, (+-)-isomerMeSH, HMDB
Chemical FormulaC9H12O4
Average Molecular Weight184.1892
Monoisotopic Molecular Weight184.073558872
IUPAC Name1-(4-hydroxy-3-methoxyphenyl)ethane-1,2-diol
Traditional Namemethoxyhydroxyphenylglycol
CAS Registry Number534-82-7
SMILES
COC1=CC(=CC=C1O)C(O)CO
InChI Identifier
InChI=1S/C9H12O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,10-12H,5H2,1H3
InChI KeyFBWPWWWZWKPJFL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-diol
  • Ether
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.13ALOGPS
logP0.11ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)9.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.28 m³·mol⁻¹ChemAxon
Polarizability18.64 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Brain
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0259702
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022651
KNApSAcK IDNot Available
Chemspider ID10348
KEGG Compound IDC05594
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceKessler J A; Gordon E K; Reid J L; Kopin I J Homovanillic acid and 3-methoxy-4-hydroxyphenylethyleneglycol production by the monkey spinal cord. Journal of neurochemistry (1976), 26(6), 1057-61.
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-Dihydroxyphenylglycol + Guaiacol → Vanylglycol + Pyrocatecholdetails