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Showing metabocard for 3,4-Dimethoxybenzoic acid (HMDB0059763)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-02-26 19:02:50 UTC
Update Date2023-02-21 17:29:21 UTC
HMDB IDHMDB0059763
Secondary Accession Numbers
  • HMDB59763
Metabolite Identification
Common Name3,4-Dimethoxybenzoic acid
Description3,4-Dimethoxybenzoic acid, also known as 3,4-dimethylprotocatechuate or veratric acid, belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. 3,4-Dimethoxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,4-Dimethoxybenzoic acid has been detected, but not quantified in, corianders and olives. This could make 3,4-dimethoxybenzoic acid a potential biomarker for the consumption of these foods. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0059763 (3,4-Dimethoxybenzoic acid)

  Mrv0541 02241221492D          

 13 13  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
  4 13  1  0  0  0  0
M  END
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3D MOL for HMDB0059763 (3,4-Dimethoxybenzoic acid)

HMDB0059763
     RDKit          3D
3,4-Dimethoxybenzoic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
   -3.0047   -1.9660    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3451   -0.7666   -0.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9715   -0.5806    0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -1.5878    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2670   -1.3171    0.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541   -0.0609    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1827    0.1973    0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6891    1.3118   -0.0839 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594   -0.8235    0.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8641    0.9363   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5079    0.6866   -0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944    1.7128   -0.6228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9664    3.0076   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0062   -1.7038    0.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4732   -2.5566    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1847   -2.5896   -0.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4706   -2.5728    0.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9367   -2.1145    0.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9092   -1.3002    1.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2199    1.9465   -0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2512    3.3141   -0.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7900    3.7490   -0.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4206    3.0780   -1.8880 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  2  0
  7  9  1  0
  6 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  9 19  1  0
 10 20  1  0
 13 21  1  0
 13 22  1  0
 13 23  1  0
M  END
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3D SDF for HMDB0059763 (3,4-Dimethoxybenzoic acid)

  Mrv0541 02241221492D          

 13 13  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
  4 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059763

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C=C(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5H,1-2H3,(H,10,11)

> <INCHI_KEY>
DAUAQNGYDSHRET-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.918655543856794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4-dimethoxybenzoic acid

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
1.315486192666666

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.142664045876819

> <JCHEM_PKA_STRONGEST_BASIC>
-4.607325586072669

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
46.2406

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
veratric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0059763 (3,4-Dimethoxybenzoic acid)

HMDB0059763
     RDKit          3D
3,4-Dimethoxybenzoic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
   -3.0047   -1.9660    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3451   -0.7666   -0.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9715   -0.5806    0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -1.5878    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2670   -1.3171    0.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541   -0.0609    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1827    0.1973    0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6891    1.3118   -0.0839 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594   -0.8235    0.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8641    0.9363   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5079    0.6866   -0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944    1.7128   -0.6228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9664    3.0076   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0062   -1.7038    0.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4732   -2.5566    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1847   -2.5896   -0.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4706   -2.5728    0.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9367   -2.1145    0.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9092   -1.3002    1.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2199    1.9465   -0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2512    3.3141   -0.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7900    3.7490   -0.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4206    3.0780   -1.8880 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  2  0
  7  9  1  0
  6 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  9 19  1  0
 10 20  1  0
 13 21  1  0
 13 22  1  0
 13 23  1  0
M  END
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PDB for HMDB0059763 (3,4-Dimethoxybenzoic acid)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12    4                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0059763 (3,4-Dimethoxybenzoic acid)

COMPND    HMDB0059763
HETATM    1  C1  UNL     1      -3.005  -1.966   0.226  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.345  -0.767  -0.039  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.972  -0.581   0.027  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.096  -1.588   0.372  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.267  -1.317   0.415  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.754  -0.061   0.120  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.183   0.197   0.172  1.00  0.00           C  
HETATM    8  O2  UNL     1       3.689   1.312  -0.084  1.00  0.00           O  
HETATM    9  O3  UNL     1       4.059  -0.823   0.520  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.864   0.936  -0.223  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.508   0.687  -0.273  1.00  0.00           C  
HETATM   12  O4  UNL     1      -1.394   1.713  -0.623  1.00  0.00           O  
HETATM   13  C9  UNL     1      -0.966   3.008  -0.933  1.00  0.00           C  
HETATM   14  H1  UNL     1      -4.006  -1.704   0.654  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.473  -2.557   0.992  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.185  -2.590  -0.677  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.471  -2.573   0.604  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.937  -2.115   0.685  1.00  0.00           H  
HETATM   19  H6  UNL     1       3.909  -1.300   1.419  1.00  0.00           H  
HETATM   20  H7  UNL     1       1.220   1.947  -0.464  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.251   3.314  -0.125  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.790   3.749  -0.876  1.00  0.00           H  
HETATM   23  H10 UNL     1      -0.421   3.078  -1.888  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   17
CONECT    5    6    6   18
CONECT    6    7   10
CONECT    7    8    8    9
CONECT    9   19
CONECT   10   11   11   20
CONECT   11   12
CONECT   12   13
CONECT   13   21   22   23
END
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SMILES for HMDB0059763 (3,4-Dimethoxybenzoic acid)

COC1=C(OC)C=C(C=C1)C(O)=O
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INCHI for HMDB0059763 (3,4-Dimethoxybenzoic acid)

InChI=1S/C9H10O4/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5H,1-2H3,(H,10,11)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3,4-Dimethylprotocatechuic acidChEBI
Dimethylprotocatechuic acidChEBI
Veratric acidChEBI
Veratrumenoic acidChEBI
Veratrylic acidChEBI
3,4-DimethylprotocatechuateGenerator
DimethylprotocatechuateGenerator
VeratrateGenerator
VeratrumenoateGenerator
VeratrylateGenerator
3,4-DimethoxybenzoateGenerator
Veratric acid, potassium saltMeSH
Veratric acid, sodium saltMeSH
Veratric acid, sodium salt, (11)C-labeledMeSH
3,4-Dimethoxybenzoic acidHMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name3,4-dimethoxybenzoic acid
Traditional Nameveratric acid
CAS Registry NumberNot Available
SMILES
COC1=C(OC)C=C(C=C1)C(O)=O
InChI Identifier
InChI=1S/C9H10O4/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5H,1-2H3,(H,10,11)
InChI KeyDAUAQNGYDSHRET-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentP-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • P-methoxybenzoic acid or derivatives
  • M-methoxybenzoic acid or derivatives
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Benzoic acid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Alkyl aryl ether
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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 LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID419
FooDB IDFDB000222
KNApSAcK IDNot Available
Chemspider ID6854
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7121
PDB IDTWO
ChEBI ID296881
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shin SW, Jung E, Kim S, Lee KE, Youm JK, Park D: Antagonist effects of veratric acid against UVB-induced cell damages. Molecules. 2013 May 10;18(5):5405-19. doi: 10.3390/molecules18055405. [PubMed:23666007 ]
  2. Pham NH, Baldo BA, Manfredi M, Zerboni R: Fine structural specificity differences of trimethoprim allergenic determinants. Clin Exp Allergy. 1996 Oct;26(10):1155-60. [PubMed:8911701 ]