Showing metabocard for Vanillic acid (MMDBc0000107)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:36:08 UTC
Update Date2024-04-30 19:31:05 UTC
Metabolite IDMMDBc0000107
Metabolite Identification
Common NameVanillic acid
DescriptionVanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavouring and scent agent that produces a pleasant, creamy odour. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea, and vanilla-flavoured confectionary. Vanillic acid selectively and specifically inhibits 5'nucleotidase activity (PMID: 16899266 ). Vanillic acid is a microbial metabolite found in Amycolatopsis, Delftia, and Pseudomonas (PMID: 11152072 , 10543794 , 11728709 , 9579070 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fe2ad6416e8>


  Mrv1652309272007382D          

 12 12  0  0  0  0            999 V2000
10021.645810020.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10024.505310022.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.221710022.2093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10024.505310023.4479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.791210022.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.076810022.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.362310022.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.362210021.3839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.076710020.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.791210021.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.076710020.1464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.791110019.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  1  8  1  0  0  0  0
  5  2  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fe2ad6416e8>

HMDB0000484
     RDKit          3D
Vanillic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.6049   -1.3196    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2208    0.0384    0.1901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8851    0.4308    0.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1369   -0.5004   -0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477   -0.0880   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5390   -1.0451   -0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7219   -0.6560   -0.4172 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3012   -2.4090   -0.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6826    1.2668   -0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6785    2.2025   -0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299    1.7858    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6786    2.7118    0.2441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342   -1.8824   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4660   -1.7969    1.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6834   -1.3890   -0.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0864   -1.5527   -0.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8252   -3.0766    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7088    1.6061   -0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8840    3.2755    0.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6364    2.3980    0.3250 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  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 12 20  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fe2ad6416e8>


  Mrv1652309272007382D          

 12 12  0  0  0  0            999 V2000
10021.645810020.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10024.505310022.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.221710022.2093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10024.505310023.4479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.791210022.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.076810022.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.362310022.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.362210021.3839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.076710020.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.791210021.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.076710020.1464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.791110019.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  1  8  1  0  0  0  0
  5  2  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000107

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=CC(=CC=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)

> <INCHI_KEY>
WKOLLVMJNQIZCI-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.148

> <EXACT_MASS>
168.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.860742490127857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3-methoxybenzoic acid

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
1.1695921366666666

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.135539077333167

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.155416072405767

> <JCHEM_PKA_STRONGEST_BASIC>
-4.901377890748089

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
41.7583

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vanillic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007fe2ad6416e8>

HMDB0000484
     RDKit          3D
Vanillic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.6049   -1.3196    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2208    0.0384    0.1901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8851    0.4308    0.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1369   -0.5004   -0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477   -0.0880   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5390   -1.0451   -0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7219   -0.6560   -0.4172 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3012   -2.4090   -0.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6826    1.2668   -0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6785    2.2025   -0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299    1.7858    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6786    2.7118    0.2441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342   -1.8824   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4660   -1.7969    1.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6834   -1.3890   -0.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0864   -1.5527   -0.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8252   -3.0766    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7088    1.6061   -0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8840    3.2755    0.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6364    2.3980    0.3250 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  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 12 20  1  0
M  END
Download

PDB for #<Metabolite:0x00007fe2ad6416e8>

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8707.0728705.813   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8712.4108708.895   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8713.7478708.124   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8712.4108710.436   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8711.0778708.123   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8709.7438708.893   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8708.4108708.123   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8708.4098706.583   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8709.7438705.813   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8711.0778706.583   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8709.7438704.273   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8711.0778703.503   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    3    4    5                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    6   10    2                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9    1                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
Download

3D PDB for #<Metabolite:0x00007fe2ad6416e8>

COMPND    HMDB0000484
HETATM    1  C1  UNL     1      -2.605  -1.320   0.173  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.221   0.038   0.190  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.885   0.431   0.076  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.137  -0.500  -0.061  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.448  -0.088  -0.173  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.539  -1.045  -0.317  1.00  0.00           C  
HETATM    7  O2  UNL     1       3.722  -0.656  -0.417  1.00  0.00           O  
HETATM    8  O3  UNL     1       2.301  -2.409  -0.349  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.683   1.267  -0.141  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.679   2.203  -0.006  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.630   1.786   0.105  1.00  0.00           C  
HETATM   12  O4  UNL     1      -1.679   2.712   0.244  1.00  0.00           O  
HETATM   13  H1  UNL     1      -2.034  -1.882  -0.601  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.466  -1.797   1.164  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.683  -1.389  -0.121  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.086  -1.553  -0.082  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.825  -3.077   0.204  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.709   1.606  -0.228  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.884   3.275   0.017  1.00  0.00           H  
HETATM   20  H8  UNL     1      -2.636   2.398   0.325  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   16
CONECT    5    6    9    9
CONECT    6    7    7    8
CONECT    8   17
CONECT    9   10   18
CONECT   10   11   11   19
CONECT   11   12
CONECT   12   20
END
Download

SMILES for #<Metabolite:0x00007fe2ad6416e8>

COC1=CC(=CC=C1O)C(O)=O
Download

INCHI for #<Metabolite:0x00007fe2ad6416e8>

InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
Download
Synonyms
ValueSource
4-Hydroxy-3-methoxybenzoic acidChEBI
4-Hydroxy-3-methoxybenzoateKegg
VanillateGenerator
3-Methoxy-4-hydroxybenzoateHMDB
3-Methoxy-4-hydroxybenzoic acidHMDB
4-Hydroxy-3-methoxy-benzoateHMDB
4-Hydroxy-3-methoxy-benzoic acidHMDB
4-Hydroxy-m-anisateHMDB
4-Hydroxy-m-anisic acidHMDB
Acide vanilliqueHMDB
p-VanillateHMDB
p-Vanillic acidHMDB
Protocatechuic acid 3-methyl esterHMDB
Acid, 4-hydroxy-3-methoxybenzoicHMDB
p Hydroxy m methoxy benzoic acidHMDB
4 Hydroxy 3 methoxybenzoic acidHMDB
Acid, vanillicHMDB
Acid, p-hydroxy-m-methoxy-benzoicHMDB
p-Hydroxy-m-methoxy-benzoic acidHMDB
2-Methoxy-4-carboxyphenolHMDB
Methylprotocatechuic acidHMDB
VAHMDB
m-Methoxy-p-hydroxy-benzoic acidHMDB
Vanillic acidKEGG
Molecular FormulaC8H8O4
Average Mass168.148
Monoisotopic Mass168.042258738
IUPAC Name4-hydroxy-3-methoxybenzoic acid
Traditional Namevanillic acid
CAS Registry Number121-34-6
SMILES
COC1=CC(=CC=C1O)C(O)=O
InChI Identifier
InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
InChI KeyWKOLLVMJNQIZCI-UHFFFAOYSA-N