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Showing metabocard for Vanylglycol (HMDB0001490)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:45 UTC
HMDB IDHMDB0001490
Secondary Accession Numbers
Metabolite Identification
Common NameVanylglycol
DescriptionVanylglycol, also known as 3-Methoxy-4-hydroxyphenylethyleneglycol (MHPG), 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. It is synthesized from endogenous epinephrine and norepinephrine in vivo. It is found in brain, blood, CSF, and urine, where its concentrations are used to measure catecholamine turnover. 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 is a O-methylated metabolite of normetanephrine. In humans, vanylglycol is involved in the metabolic disorder called tyrosinemia in newborns. 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.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001490 (Vanylglycol)

  Mrv1652305271900322D          

 13 13  0  0  0  0            999 V2000
   11.0364  -11.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0364  -12.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7508  -12.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4653  -12.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4653  -11.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7508  -10.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3219  -12.5376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7508  -13.3626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0364  -13.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1798  -10.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1798  -10.0626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8943  -11.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6088  -10.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for HMDB0001490 (Vanylglycol)

HMDB0001490
     RDKit          3D
Vanylglycol
 25 25  0  0  0  0  0  0  0  0999 V2000
    3.0348    0.2967    0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5029   -0.8974    0.2869 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1911   -1.0128   -0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3094    0.0751   -0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969   -0.0067   -0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8737    1.1591   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9806    0.9103    0.4868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1415    2.3591    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0717    2.7029   -0.6572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4199   -1.2223   -0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5687   -2.2948   -1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7445   -2.2060   -0.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6225   -3.2964   -0.7454 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0061    0.1200    1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409    1.0359    0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665    0.7077    1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7619    0.9689    0.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2941    1.3683   -1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4064    0.0432    0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611    2.1739    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8149    3.2567    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2827    2.4618   -1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4442   -1.2936   -1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931   -3.2619   -1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2690   -4.1476   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  5 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
M  END
Download

3D SDF for HMDB0001490 (Vanylglycol)

  Mrv1652305271900322D          

 13 13  0  0  0  0            999 V2000
   11.0364  -11.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0364  -12.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7508  -12.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4653  -12.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4653  -11.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7508  -10.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3219  -12.5376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7508  -13.3626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0364  -13.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1798  -10.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1798  -10.0626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8943  -11.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6088  -10.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001490

> <DATABASE_NAME>
hmdb

> <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_KEY>
FBWPWWWZWKPJFL-UHFFFAOYSA-N

> <FORMULA>
C9H12O4

> <MOLECULAR_WEIGHT>
184.1892

> <EXACT_MASS>
184.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
18.636009577166565

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-hydroxy-3-methoxyphenyl)ethane-1,2-diol

> <ALOGPS_LOGP>
-0.13

> <JCHEM_LOGP>
0.11432451933333344

> <ALOGPS_LOGS>
-1.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.741893489428545

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.909148631409135

> <JCHEM_PKA_STRONGEST_BASIC>
-2.97784960091455

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
47.2805

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methoxyhydroxyphenylglycol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0001490 (Vanylglycol)

HMDB0001490
     RDKit          3D
Vanylglycol
 25 25  0  0  0  0  0  0  0  0999 V2000
    3.0348    0.2967    0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5029   -0.8974    0.2869 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1911   -1.0128   -0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3094    0.0751   -0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969   -0.0067   -0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8737    1.1591   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9806    0.9103    0.4868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1415    2.3591    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0717    2.7029   -0.6572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4199   -1.2223   -0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5687   -2.2948   -1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7445   -2.2060   -0.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6225   -3.2964   -0.7454 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0061    0.1200    1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409    1.0359    0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665    0.7077    1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7619    0.9689    0.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2941    1.3683   -1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4064    0.0432    0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611    2.1739    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8149    3.2567    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2827    2.4618   -1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4442   -1.2936   -1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931   -3.2619   -1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2690   -4.1476   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  5 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
M  END
Download

PDB for HMDB0001490 (Vanylglycol)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      20.601 -21.094   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.601 -22.634   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.935 -23.404   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.269 -22.634   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.269 -21.094   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.935 -20.324   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      19.268 -23.404   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      21.935 -24.944   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      20.601 -25.714   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.602 -20.324   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      24.602 -18.784   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      25.936 -21.094   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      27.270 -20.324   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    2                                                            
CONECT    8    3    9                                                       
CONECT    9    8                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0001490 (Vanylglycol)

COMPND    HMDB0259702
HETATM    1  C1  UNL     1       2.385   2.121  -0.045  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.656   0.739   0.055  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.658  -0.221   0.025  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.345   0.150  -0.106  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.696  -0.767  -0.142  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.108  -0.412  -0.281  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.945  -1.103   0.598  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.377   1.059  -0.108  1.00  0.00           C  
HETATM    9  O3  UNL     1      -2.131   1.497   1.183  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.358  -2.100  -0.039  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.969  -2.498   0.095  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.967  -1.546   0.125  1.00  0.00           C  
HETATM   13  O4  UNL     1       3.306  -1.940   0.260  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.250   2.725   0.294  1.00  0.00           H  
HETATM   15  H2  UNL     1       1.548   2.341   0.669  1.00  0.00           H  
HETATM   16  H3  UNL     1       2.104   2.413  -1.059  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.093   1.197  -0.186  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.420  -0.675  -1.323  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.775  -0.608   0.778  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.853   1.683  -0.859  1.00  0.00           H  
HETATM   21  H8  UNL     1      -3.473   1.209  -0.300  1.00  0.00           H  
HETATM   22  H9  UNL     1      -2.374   2.457   1.211  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.087  -2.886  -0.056  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.254  -3.538   0.177  1.00  0.00           H  
HETATM   25  H12 UNL     1       4.061  -1.296   0.287  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5   17
CONECT    5    6   10   10
CONECT    6    7    8   18
CONECT    7   19
CONECT    8    9   20   21
CONECT    9   22
CONECT   10   11   23
CONECT   11   12   12   24
CONECT   12   13
CONECT   13   25
END
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SMILES for HMDB0001490 (Vanylglycol)

COC1=CC(=CC=C1O)C(O)CO
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INCHI for HMDB0001490 (Vanylglycol)

InChI=1S/C9H12O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,10-12H,5H2,1H3
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View in JSmolView Stereo Labels
Synonyms
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
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Brain
  • Platelet
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Multi-infarct dementia
  1. 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. [PubMed:9116178 ]
Cortical myoclonus
  1. 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. [PubMed:15557528 ]
Aromatic L-amino acid decarboxylase deficiency
  1. 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. [PubMed:16288991 ]
Cognitive disorders
  1. Hildebrand J, Bourgeois F, Buyse M, Przedborski S, Goldman S: Reproducibility of monoamine metabolite measurements in human cerebrospinal fluid. Acta Neurol Scand. 1990 May;81(5):427-30. [PubMed:1695809 ]
Schizophrenia
  1. 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. [PubMed:115032 ]
  2. Alfredsson G, Wiesel FA: Monoamine metabolites and amino acids in serum from schizophrenic patients before and during sulpiride treatment. Psychopharmacology (Berl). 1989;99(3):322-7. [PubMed:2480613 ]
  3. Pickar D, Breier A, Hsiao JK, Doran AR, Wolkowitz OM, Pato CN, Konicki PE, Potter WZ: Cerebrospinal fluid and plasma monoamine metabolites and their relation to psychosis. Implications for regional brain dysfunction in schizophrenia. Arch Gen Psychiatry. 1990 Jul;47(7):641-8. [PubMed:1694425 ]
  4. Bjerkenstedt L, Edman G, Hagenfeldt L, Sedvall G, Wiesel FA: Plasma amino acids in relation to cerebrospinal fluid monoamine metabolites in schizophrenic patients and healthy controls. Br J Psychiatry. 1985 Sep;147:276-82. [PubMed:2415198 ]
  5. Zumarraga M, Davila R, Basterreche N, Arrue A, Goienetxea B, Zamalloa MI, Erkoreka L, Bustamante S, Inchausti L, Gonzalez-Torres MA, Guimon J: Catechol O-methyltransferase and monoamine oxidase A genotypes, and plasma catecholamine metabolites in bipolar and schizophrenic patients. Neurochem Int. 2010 May-Jun;56(6-7):774-9. doi: 10.1016/j.neuint.2010.02.015. Epub 2010 Mar 4. [PubMed:20206656 ]
Epilepsy
  1. Botez MI, Young SN: Effects of anticonvulsant treatment and low levels of folate and thiamine on amine metabolites in cerebrospinal fluid. Brain. 1991 Feb;114 ( Pt 1A):333-48. [PubMed:1705463 ]
Panic disorder
  1. 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. [PubMed:1712114 ]
Olivopontocerebral atrophy
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Hereditary spastic paraplegia
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Friedreich's ataxia
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Major depressive disorder
  1. Sheline Y, Bardgett ME, Csernansky JG: Correlated reductions in cerebrospinal fluid 5-HIAA and MHPG concentrations after treatment with selective serotonin reuptake inhibitors. J Clin Psychopharmacol. 1997 Feb;17(1):11-4. [PubMed:9004051 ]
Sepiapterin reductase deficiency
  1. Verbeek MM, Willemsen MA, Wevers RA, Lagerwerf AJ, Abeling NG, Blau N, Thony B, Vargiami E, Zafeiriou DI: Two Greek siblings with sepiapterin reductase deficiency. Mol Genet Metab. 2008 Aug;94(4):403-9. doi: 10.1016/j.ymgme.2008.04.003. Epub 2008 May 27. [PubMed:18502672 ]
Parkinson's disease
  1. Dizdar N, Kagedal B, Lindvall B: Treatment of Parkinson's disease with NADH. Acta Neurol Scand. 1994 Nov;90(5):345-7. [PubMed:7887134 ]
Brunner Syndrome
  1. Brunner HG, Nelen MR, van Zandvoort P, Abeling NG, van Gennip AH, Wolters EC, Kuiper MA, Ropers HH, van Oost BA: X-linked borderline mental retardation with prominent behavioral disturbance: phenotype, genetic localization, and evidence for disturbed monoamine metabolism. Am J Hum Genet. 1993 Jun;52(6):1032-9. [PubMed:8503438 ]
Associated OMIM IDs
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000330
Good Scents 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 References

Enzymes

Enzyme Details
1. Catechol O-methyltransferase
General function:
Involved in magnesium ion binding
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.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
S-Adenosylmethionine + 3,4-Dihydroxyphenylglycol → S-Adenosylhomocysteine + Vanylglycoldetails