3-methoxy-4-hydroxyphenylglycol (PAMDB120410)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120410
Identification
Name: 3-methoxy-4-hydroxyphenylglycol
Description:Vanylglycol (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 ).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • methoxyhydroxyphenylglycolvanylglycol
  • MHPG
  • MOPEG
  • methoxy-hydroxyphenyl glycol
  • 4-hydroxy-3-methoxyphenylglycolhydroxymethoxyphenylglycol
  • HMPG
Chemical Formula: C9H12O4
Average Molecular Weight: 184.191
Monoisotopic Molecular Weight: 184.07356
InChI Key: FBWPWWWZWKPJFL-QMMMGPOBSA-N
InChI:InChI=1S/C9H12O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,10-12H,5H2,1H3/t8-/m0/s1
CAS number: 534-82-7
IUPAC Name:1-(4-hydroxy-3-methoxyphenyl)ethane-1,2-diol
Traditional IUPAC Name: methoxyhydroxyphenylglycol
SMILES:COC1(=C(O)C=CC(C(O)CO)=C1)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
Kingdom Organic compounds
Super ClassBenzenoids
Class Phenols
Sub ClassMethoxyphenols
Direct Parent Methoxyphenols
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 Framework Aromatic homomonocyclic compounds
External Descriptors
  • phenols, methoxybenzene (CHEBI:1576)
  • a guaiacol (CPD-11497)
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.99 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.28 m3·mol-1ChemAxon
Polarizability18.64 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
3-methoxy-4-hydroxyphenylglycol + NAD+ → 3-methoxy-4-hydroxyphenylglycolaldehyde + NADH + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0uxr-0900000000-fb2c82b5598c8c9bab3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-0900000000-a449b185542d66dc0be8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-006x-9600000000-316d1194b9b0ed76d178View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-f104dd3883189a74b622View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0900000000-040295df7423a417edabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f72-3900000000-87310e73492350a05b5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-01cbe4fce361c48afabfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05ur-1900000000-b4ac6a118c11eb31a6ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-4a1c057f8cdd445e7125View in MoNA
1D NMR1H NMR SpectrumNot Available
References
References:
  • Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [9849813 ]
  • Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. [8884658 ]
  • Javors MA, Bowden CL, Maas JW: 3-methoxy-4-hydroxyphenylglycol, 5-hydroxyindoleacetic acid, and homovanillic acid in human cerebrospinal fluid. Storage and measurement by reversed-phase high-performance liquid chromatography and coulometric detection using 3-methoxy-4-hydroxyphenyllactic acid as an internal standard. J Chromatogr. 1984 Dec 12;336(2):259-69. [6085084 ]
  • Eriksson E, Westberg P, Alling C, Thuresson K, Modigh K: Cerebrospinal fluid levels of monoamine metabolites in panic disorder. Psychiatry Res. 1991 Mar;36(3):243-51. [1712114 ]
  • Sullivan GM, Oquendo MA, Huang YY, Mann JJ: Elevated cerebrospinal fluid 5-hydroxyindoleacetic acid levels in women with comorbid depression and panic disorder. Int J Neuropsychopharmacol. 2006 Oct;9(5):547-56. Epub 2005 Nov 1. [16259647 ]
  • von Holst H, Lindquist C, Sedvall G: Increased concentrations of the monoamine metabolites homovanillic acid and 5-hydroxyindoleacetic acid in lumbar and central CSF and of 3-methoxy-4-hydroxyphenylglycol in lumbar CSF after subarachnoid haemorrhage. Acta Neurochir (Wien). 1985;77(3-4):146-51. [2416192 ]
  • Harnryd C, Bjerkenstedt L, Grimm VE, Sedvall G: Reduction of MOPEG levels in cerebrospinal fluid of psychotic women after electroconvulsive treatment. Psychopharmacology (Berl). 1979 Aug 8;64(2):131-4. [115032 ]
  • Brautigam C, Wevers RA, Jansen RJ, Smeitink JA, de Rijk-van Andel JF, Gabreels FJ, Hoffmann GF: Biochemical hallmarks of tyrosine hydroxylase deficiency. Clin Chem. 1998 Sep;44(9):1897-904. [9732974 ]
  • Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [6198473 ]
  • Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. [16288991 ]
  • Frankenhaeuser M, Lundberg U, Rauste von Wright M, von Wright J, Sedvall G: Urinary monoamine metabolites as indices of mental stress in healthy males and females. Pharmacol Biochem Behav. 1986 Jun;24(6):1521-5. [2426718 ]
  • Leuzzi V, Di Sabato ML, Zollino M, Montanaro ML, Seri S: Early-onset encephalopathy and cortical myoclonus in a boy with MECP2 gene mutation. Neurology. 2004 Nov 23;63(10):1968-70. [15557528 ]
  • Wallin A, Blennow K, Edman A, Mansson JE: Decreased lumbar cerebrospinal fluid levels of monoamine metabolites in vascular dementia. Int Psychogeriatr. 1996 Fall;8(3):425-36. [9116178 ]
  • Kawamura M, Eisenhofer G, Kopin IJ, Kador PF, Lee YS, Fujisawa S, Sato S: Aldose reductase: an aldehyde scavenging enzyme in the intraneuronal metabolism of norepinephrine in human sympathetic ganglia. Auton Neurosci. 2002 Mar 18;96(2):131-9. [11958479 ]
  • Evangelou AM, Malamas MP, Vezyraki P, Karkabounas SC: Is epinephrine-induced platelet aggregation autoregulated by its metabolic degradation products in vivo? In Vivo. 1998 May-Jun;12(3):321-5. [9706478 ]
  • Rollag J, Liu T, Hage DS: Determination of 3-methoxy-4-hydroxyphenylethylene glycol in urine using reversed-phase liquid chromatography with column switching and electrochemical detection. J Chromatogr B Biomed Appl. 1995 Jan 20;663(2):193-200. [7735466 ]
  • Brewerton TD, Berrettini WH, Nurnberger JI Jr, Linnoila M: Analysis of seasonal fluctuations of CSF monoamine metabolites and neuropeptides in normal controls: findings with 5HIAA and HVA. Psychiatry Res. 1988 Mar;23(3):257-65. [2455302 ]
Synthesis Reference: Kessler 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) Download (PDF)
External Links:
ResourceLink
HMDBHMDB01490
CHEMSPIDER10348
LIGAND-CPDC05594
PUBCHEM10805