Showing NP-Card for Vanylglycol (NP0000930)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2025-02-11 15:41:45 UTC
NP-MRD IDNP0000930
Secondary Accession NumbersNone
Natural Product 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 NP0000930 (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 NP0000930 (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 NP0000930 (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>
NP0000930

> <DATABASE_NAME>
NP-MRD

> <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 NP0000930 (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 NP0000930 (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 NP0000930 (Vanylglycol)

COMPND    HMDB0001490
HETATM    1  C1  UNL     1       3.035   0.297   0.828  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.503  -0.897   0.287  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.191  -1.013  -0.127  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.309   0.075  -0.027  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.997  -0.007  -0.430  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.874   1.159  -0.325  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.981   0.910   0.487  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.142   2.359   0.161  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.072   2.703  -0.657  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.420  -1.222  -0.946  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.569  -2.295  -1.050  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.744  -2.206  -0.643  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.622  -3.296  -0.745  1.00  0.00           O  
HETATM   14  H1  UNL     1       4.006   0.120   1.334  1.00  0.00           H  
HETATM   15  H2  UNL     1       3.141   1.036   0.008  1.00  0.00           H  
HETATM   16  H3  UNL     1       2.367   0.708   1.640  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.762   0.969   0.411  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.294   1.368  -1.337  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.406   0.043   0.301  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.761   2.174   1.208  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.815   3.257   0.173  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.283   2.462  -1.599  1.00  0.00           H  
HETATM   23  H10 UNL     1      -2.444  -1.294  -1.263  1.00  0.00           H  
HETATM   24  H11 UNL     1      -0.893  -3.262  -1.457  1.00  0.00           H  
HETATM   25  H12 UNL     1       1.269  -4.148  -1.124  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 NP0000930 (Vanylglycol)

COC1=CC(=CC=C1O)C(O)CO
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INCHI for NP0000930 (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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Synonyms
Chemical FormulaC9H12O4
Average Mass184.1892 Da
Monoisotopic Mass184.07356 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-08View Spectrum
Species
Species of Origin
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
HMDB IDHMDB0001490
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030440
KNApSAcK IDNot Available
Chemspider ID10348
KEGG Compound IDC05594
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6274
PubChem Compound10805
PDB IDNot Available
ChEBI ID846276
Good Scents IDNot Available
References
General References