General Information of MET (ID: META01175)
Name Vanylglycol
Synonyms   Click to Show/Hide Synonyms of This Metabolite
Vanylglycol; MHPG; 534-82-7; 3-Methoxy-4-hydroxyphenylglycol; Hydroxymethoxyphenylglycol; MOPEG; METHOXYHYDROXYPHENYLGLYCOL; 1-(4-hydroxy-3-methoxyphenyl)ethane-1,2-diol; 1-(4-Hydroxy-3-methoxyphenyl)-1,2-ethanediol; 3-Methoxy-4-hydroxyphenylethyleneglycol; CHEBI:1576; HMPG; 4-Hydroxy-3-methoxyphenylglycol; (4-Hydroxy-3-methoxyphenyl)ethylene glycol; 4-Hydroxy-3-methoxyphenyl glycol
Source Aromatic homomonocyclic compounds
Structure Type   Methoxyphenols  (Click to Show/Hide the Complete Structure Type Hierarchy)
Benzenoids
Phenols
Methoxyphenols
PubChem CID
10805
HMDB ID
HMDB0001490
Formula
C9H12O4
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=10805"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C05594
ChEBI ID
846276
FooDB ID
FDB022651
ChemSpider ID
10348
METLIN ID
6274
Physicochemical Properties Molecular Weight 184.19 Topological Polar Surface Area 69.9
XlogP -0.7 Complexity 151
Heavy Atom Count 13 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Function
Vanylglycol, also known as MHPG or MOPEG, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Catecholamines play an important role in platelet activation and aggregation, epinephrine being the most potent one. vanylglycol and pyrocatechol can be biosynthesized from 3,4-dihydroxyphenylglycol and guaiacol; which is catalyzed by the enzyme catechol O-methyltransferase. Vanylglycol (MHPG) is a O-methylated metabolite of normetanephrine. In humans, vanylglycol is involved in the metabolic disorder called tyrosinemia, transient, of the newborn. Alcohol consumption increases the level of Vanylglycol in urine and CSF. Vanylglycol is found normally in urine, in plasma and cerebrospinal fluid. Outside of the human body, vanylglycol has been detected, but not quantified in, several different foods, such as blackcurrants, chinese bayberries, elderberries, oriental wheats, and poppies. This could make vanylglycol a potential biomarker for the consumption of these foods. Catecholamines are substantially increased during stress, exercise or smoking and could result in clinically important platelet activation if their action was not rapidly regulated. Vanylglycol has been found to be associated with several diseases such as multi-infarct dementia, epilepsy, hereditary spastic paraplegia, and schizophrenia; also vanylglycol has been linked to the inborn metabolic disorders including aromatic l-amino acid decarboxylase deficiency. Vanylglycol is formed by catechol-O-methyltransferase (COMT) from norepinephrine. Alcohol dehydrogenase has been shown to act on norepinephrine and produce HMPG.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      GPCR glutamate (GPCR-3)
            Glutamate receptor mGLU2 (mGluR2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of Grm2
                      Induced Change Vanylglycol concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of mGlu2/3 leads to the increase of vanylglycol levels compared with control group.
            Glutamate receptor mGLU3 (mGluR3) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of Grm3
                      Induced Change Vanylglycol concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of mGlu2/3 leads to the increase of vanylglycol levels compared with control group.
References
1 Decreased striatal dopamine in group II metabotropic glutamate receptor (mGlu2/mGlu3) double knockout mice. BMC Neurosci. 2013 Sep 22;14:102.

If you find any error in data or bug in web service, please kindly report it to Dr. Zhang and Dr. Mou.