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Showing metabocard for Homoveratric acid (HMDB0000434)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:49 UTC
HMDB IDHMDB0000434
Secondary Accession Numbers
  • HMDB00434
Metabolite Identification
Common NameHomoveratric acid
DescriptionHomoveratric acid, also known as homoveratrumate, belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. Homoveratric acid is found, on average, in the highest concentration within olives (Olea europaea). Homoveratric acid has also been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make homoveratric acid a potential biomarker for the consumption of these foods. Homoveratric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Homoveratric acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000434 (Homoveratric acid)

3,4-Dimethoxyphenylacetic acid.mol
  Mrv1652305271900152D          

 14 14  0  0  0  0            999 V2000
    1.7862   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  2  0  0  0  0
  2  5  1  0  0  0  0
 11 12  1  0  0  0  0
  8 11  1  0  0  0  0
 13 14  1  0  0  0  0
  7 13  1  0  0  0  0
M  END
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3D MOL for HMDB0000434 (Homoveratric acid)

HMDB0000434
     RDKit          3D
Homoveratric acid
 26 26  0  0  0  0  0  0  0  0999 V2000
    3.3641    2.2493    0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7882    1.0146   -0.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565    0.6960    0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5849    1.6198    0.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7470    1.3335    0.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1949    0.0809    0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5849   -0.3388    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618   -0.0807   -0.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0917    0.4576   -1.4617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7914   -0.4447   -0.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3106   -0.8550    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0221   -0.5649   -0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9258   -1.4593   -0.7274 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6252   -2.7594   -1.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4239    2.3440    1.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4073    2.2433   -0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8450    3.0928   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9172    2.6147    0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439    2.0206    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6255   -1.4129    1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9836    0.2310    1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2481   -0.8169    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420   -1.8492   -0.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4372   -3.0929   -1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669   -2.8460   -1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6612   -3.4776   -0.2738 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12  3  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  7 20  1  0
  7 21  1  0
 10 22  1  0
 11 23  1  0
 14 24  1  0
 14 25  1  0
 14 26  1  0
M  END
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3D SDF for HMDB0000434 (Homoveratric acid)

3,4-Dimethoxyphenylacetic acid.mol
  Mrv1652305271900152D          

 14 14  0  0  0  0            999 V2000
    1.7862   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  2  0  0  0  0
  2  5  1  0  0  0  0
 11 12  1  0  0  0  0
  8 11  1  0  0  0  0
 13 14  1  0  0  0  0
  7 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000434

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(CC(O)=O)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O4/c1-13-8-4-3-7(6-10(11)12)5-9(8)14-2/h3-5H,6H2,1-2H3,(H,11,12)

> <INCHI_KEY>
WUAXWQRULBZETB-UHFFFAOYSA-N

> <FORMULA>
C10H12O4

> <MOLECULAR_WEIGHT>
196.1999

> <EXACT_MASS>
196.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.73541977781273

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dimethoxyphenyl)acetic acid

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.2956515739999999

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.861393687418164

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5925778261371315

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
50.292

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dimethoxyphenylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000434 (Homoveratric acid)

HMDB0000434
     RDKit          3D
Homoveratric acid
 26 26  0  0  0  0  0  0  0  0999 V2000
    3.3641    2.2493    0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7882    1.0146   -0.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565    0.6960    0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5849    1.6198    0.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7470    1.3335    0.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1949    0.0809    0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5849   -0.3388    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618   -0.0807   -0.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0917    0.4576   -1.4617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7914   -0.4447   -0.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3106   -0.8550    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0221   -0.5649   -0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9258   -1.4593   -0.7274 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6252   -2.7594   -1.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4239    2.3440    1.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4073    2.2433   -0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8450    3.0928   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9172    2.6147    0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439    2.0206    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6255   -1.4129    1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9836    0.2310    1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2481   -0.8169    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420   -1.8492   -0.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4372   -3.0929   -1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669   -2.8460   -1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6612   -3.4776   -0.2738 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12  3  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  7 20  1  0
  7 21  1  0
 10 22  1  0
 11 23  1  0
 14 24  1  0
 14 25  1  0
 14 26  1  0
M  END
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PDB for HMDB0000434 (Homoveratric acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3,4-Dimethoxyphenylacetic acid.mol                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       3.334  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.334   0.000   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.668  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.667  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.667  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.001  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.001   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.667   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.334   0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.668  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    6   10    2                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11   12    8                                                       
CONECT   12   11                                                            
CONECT   13   14    7                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for HMDB0000434 (Homoveratric acid)

COMPND    HMDB0000434
HETATM    1  C1  UNL     1       3.364   2.249   0.269  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.788   1.015  -0.040  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.456   0.696   0.160  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.585   1.620   0.698  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.747   1.334   0.909  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.195   0.081   0.563  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.585  -0.339   0.740  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.462  -0.081  -0.396  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.092   0.458  -1.462  1.00  0.00           O  
HETATM   10  O3  UNL     1      -4.791  -0.445  -0.317  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.311  -0.855   0.018  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.022  -0.565  -0.192  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.926  -1.459  -0.727  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.625  -2.759  -1.125  1.00  0.00           C  
HETATM   15  H1  UNL     1       3.424   2.344   1.370  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.407   2.243  -0.140  1.00  0.00           H  
HETATM   17  H3  UNL     1       2.845   3.093  -0.218  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.917   2.615   0.978  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.444   2.021   1.321  1.00  0.00           H  
HETATM   20  H6  UNL     1      -2.625  -1.413   1.076  1.00  0.00           H  
HETATM   21  H7  UNL     1      -2.984   0.231   1.631  1.00  0.00           H  
HETATM   22  H8  UNL     1      -5.248  -0.817   0.485  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.642  -1.849  -0.262  1.00  0.00           H  
HETATM   24  H10 UNL     1       2.437  -3.093  -1.821  1.00  0.00           H  
HETATM   25  H11 UNL     1       0.667  -2.846  -1.677  1.00  0.00           H  
HETATM   26  H12 UNL     1       1.661  -3.478  -0.274  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5   18
CONECT    5    6    6   19
CONECT    6    7   11
CONECT    7    8   20   21
CONECT    8    9    9   10
CONECT   10   22
CONECT   11   12   12   23
CONECT   12   13
CONECT   13   14
CONECT   14   24   25   26
END
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SMILES for HMDB0000434 (Homoveratric acid)

COC1=CC=C(CC(O)=O)C=C1OC
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INCHI for HMDB0000434 (Homoveratric acid)

InChI=1S/C10H12O4/c1-13-8-4-3-7(6-10(11)12)5-9(8)14-2/h3-5H,6H2,1-2H3,(H,11,12)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-(3,4-Dimethoxyphenyl)acetic acidChEBI
2-(3,4-Dimethoxyphenyl)ethanoic acidChEBI
3,4-Dimethoxybenzeneacetic acidChEBI
3,4-Dimethoxyphenylacetic acidChEBI
Homoveratrumic acidChEBI
2-(3,4-Dimethoxyphenyl)acetateGenerator
2-(3,4-Dimethoxyphenyl)ethanoateGenerator
3,4-DimethoxybenzeneacetateGenerator
3,4-DimethoxyphenylacetateGenerator
HomoveratrumateGenerator
HomoveratrateGenerator
(3,4-Dimethoxyphenyl)acetateHMDB
(3,4-Dimethoxyphenyl)acetic acidHMDB
Chemical FormulaC10H12O4
Average Molecular Weight196.1999
Monoisotopic Molecular Weight196.073558872
IUPAC Name2-(3,4-dimethoxyphenyl)acetic acid
Traditional Name3,4-dimethoxyphenylacetic acid
CAS Registry Number93-40-3
SMILES
COC1=CC=C(CC(O)=O)C=C1OC
InChI Identifier
InChI=1S/C10H12O4/c1-13-8-4-3-7(6-10(11)12)5-9(8)14-2/h3-5H,6H2,1-2H3,(H,11,12)
InChI KeyWUAXWQRULBZETB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassMethoxybenzenes
Direct ParentDimethoxybenzenes
Alternative Parents
Substituents
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point96 °CNot 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 Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID575
FooDB IDFDB000317
KNApSAcK IDNot Available
Chemspider ID6872
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5423
PubChem Compound7139
PDB IDNot Available
ChEBI ID86655
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAboulezz, A. F.; Quelet, R. Derivatives of veratrole. Synthesis of homoveratric acid and some substituted diphenylmethane and fluorenone derivatives. Journal of Chemistry of the United Arab Republic (1962), 5(2), 137-46.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hempel K, Ullrich H, Philippu G: Quantitative investigation on the urinary excretion and metabolism of 3,4-dimethoxyphenylethylamine in schizophrenics and normal individuals. Biol Psychiatry. 1982 Jan;17(1):49-59. [PubMed:7059639 ]
  2. PROENCA J, WENNER J: [ON THE EFFECT OF NIKETHAMIDE AND HOMOVERATRIC ACID DIMETHYLAMIDE ON RESPIRATION IN INFANTS]. Monatsschr Kinderheilkd. 1965 Apr;113:341-3. [PubMed:14311254 ]
  3. Friedhoff AJ, Park S, Schweitzer JW, Burdock EI, Armour M: Excretion of 3,4-dimethoxyphenethylamine (DMPEA) by acute schizophrenics and controls. Biol Psychiatry. 1977 Oct;12(5):643-54. [PubMed:588645 ]
  4. Charlton CG, Crowell B Jr: Effects of dopamine metabolites on locomotor activities and on the binding of dopamine: relevance to the side effects of L-dopa. Life Sci. 2000 Apr 21;66(22):2159-71. [PubMed:10834300 ]