Record Information
Version1.0
Creation date2011-09-21 00:17:27 UTC
Update date2020-04-21 18:02:16 UTC
Primary IDFDB022651
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameVanylglycol
DescriptionVanylglycol (MHPG) is a O-methylated metabolite of normetanephrine. MHPG is formed by catechol-O-methyltransferase (COMT) from norepinephrine. Catecholamines play an important role in platelet activation and aggregation, epinephrine being the most potent one. Catecholamines are substantially increased during stress, exercise or smoking and could result in clinically important platelet activation if their action was not rapidly regulated. MHPG is found normally in urine, in plasma and cerebrospinal fluid. Alcohol consumption increases the level of HMPG in urine and CSF. Alcohol dehydrogenase has been shown to act on norepinephrine and produce HMPG. (PMID: 11958479, 9706478, 7735466, 2455302) [HMDB]. Vanylglycol is found in many foods, some of which are chervil, pummelo, peanut, and onion-family vegetables.
CAS Number534-82-7
Structure
Thumb
Synonyms
SynonymSource
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
(3-Methoxy-4-hydroxyphenyl)ethylene glycolhmdb
(4-Hydroxy-3-methoxyphenyl)ethylene glycolhmdb
4-Hydroxy-3-methoxyphenethylene glycolhmdb
Vanylglycolhmdb
Predicted Properties
PropertyValueSource
Water Solubility8.99 g/LALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H12O4
IUPAC name1-(4-hydroxy-3-methoxyphenyl)ethane-1,2-diol
InChI IdentifierInChI=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
Isomeric SMILESCOC1=CC(=CC=C1O)C(O)CO
Average Molecular Weight184.1892
Monoisotopic Molecular Weight184.073558872
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSVanylglycol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-2900000000-85ebe9a57a84ddca41b6Spectrum
Predicted GC-MSVanylglycol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-7149000000-54b71f18882477571debSpectrum
Predicted GC-MSVanylglycol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVanylglycol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVanylglycol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVanylglycol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVanylglycol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVanylglycol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVanylglycol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVanylglycol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVanylglycol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVanylglycol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVanylglycol, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVanylglycol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVanylglycol, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVanylglycol, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVanylglycol, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0uxr-0900000000-fb2c82b5598c8c9bab3aSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-0900000000-a449b185542d66dc0be8Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-006x-9600000000-316d1194b9b0ed76d178Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-f104dd3883189a74b622Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0900000000-040295df7423a417edabSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f72-3900000000-87310e73492350a05b5cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-01cbe4fce361c48afabfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05ur-1900000000-b4ac6a118c11eb31a6ffSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-4a1c057f8cdd445e7125Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004r-0900000000-df828b6c78ec969e404fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-4900000000-97f0c28e2ac7713a8fc5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9100000000-ed2fd3623e179bd8e27fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-0900000000-9b55b059e2dc27b7380fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-2900000000-44ed0b094433b8f04721Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053u-6900000000-4de993e85915570061f3Spectrum
NMRNot Available
ChemSpider ID10348
ChEMBL IDCHEMBL1322392
KEGG Compound IDC05594
Pubchem Compound ID10805
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01490
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMHPG
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference