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Showing metabocard for Vanillic acid (HMDB0000484)

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enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:52 UTC
HMDB IDHMDB0000484
Secondary Accession Numbers
  • HMDB00484
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
Data?1676999692
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000484 (Vanillic acid)


  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
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3D MOL for HMDB0000484 (Vanillic acid)

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 HMDB0000484 (Vanillic acid)


  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>
HMDB0000484

> <DATABASE_NAME>
hmdb

> <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 HMDB0000484 (Vanillic acid)

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
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PDB for HMDB0000484 (Vanillic acid)

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
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3D PDB for HMDB0000484 (Vanillic acid)

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
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SMILES for HMDB0000484 (Vanillic acid)

COC1=CC(=CC=C1O)C(O)=O
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INCHI for HMDB0000484 (Vanillic acid)

InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
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View in JSmolView Stereo Labels
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
Chemical FormulaC8H8O4
Average Molecular Weight168.148
Monoisotopic Molecular Weight168.042258738
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentM-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • M-methoxybenzoic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • Benzoic acid
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point211.5 °CNot Available
Boiling Point353.43 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.5 mg/mL at 14 °CYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP1.43HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos136.22430932474
[M+H]+Not Available136.26http://allccs.zhulab.cn/database/detail?ID=AllCCS00000527
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.7 g/LALOGPS
logP1.7ALOGPS
logP1.17ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.76 m³·mol⁻¹ChemAxon
Polarizability15.86 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.54231661259
DarkChem[M-H]-136.88431661259
AllCCS[M+H]+135.70632859911
AllCCS[M-H]-131.55232859911
DeepCCS[M+H]+133.84130932474
DeepCCS[M-H]-130.01330932474
DeepCCS[M-2H]-167.44530932474
DeepCCS[M+Na]+142.98430932474
AllCCS[M+H]+135.732859911
AllCCS[M+H-H2O]+131.332859911
AllCCS[M+NH4]+139.832859911
AllCCS[M+Na]+141.032859911
AllCCS[M-H]-131.632859911
AllCCS[M+Na-2H]-132.632859911
AllCCS[M+HCOO]-133.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Vanillic acidCOC1=C(O)C=CC(=C1)C(O)=O2743.8Standard polar33892256
Vanillic acidCOC1=C(O)C=CC(=C1)C(O)=O1534.7Standard non polar33892256
Vanillic acidCOC1=C(O)C=CC(=C1)C(O)=O1574.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Vanillic acid,1TMS,isomer #1COC1=CC(C(=O)O)=CC=C1O[Si](C)(C)C1737.3Semi standard non polar33892256
Vanillic acid,1TMS,isomer #2COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O1665.0Semi standard non polar33892256
Vanillic acid,2TMS,isomer #1COC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1768.7Semi standard non polar33892256
Vanillic acid,1TBDMS,isomer #1COC1=CC(C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C1986.9Semi standard non polar33892256
Vanillic acid,1TBDMS,isomer #2COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O1925.7Semi standard non polar33892256
Vanillic acid,2TBDMS,isomer #1COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2233.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Vanillic acid GC-MS (2 TMS)splash10-0hp2-2691000000-8409d9c758b023c6576b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Vanillic acid EI-B (Non-derivatized)splash10-0gb9-2900000000-ccd8d4a214bc1a7f08c52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Vanillic acid GC-MS (Non-derivatized)splash10-0hp2-2691000000-8409d9c758b023c6576b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Vanillic acid GC-EI-TOF (Non-derivatized)splash10-0g0b-2981000000-a58243e35d1e3a64d2aa2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0g4i-1900000000-851f4a1738be8dd91d472016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-7390000000-18c5f822b380ea00aa262017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0gb9-6900000000-c13506201c3612fc7ca52015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-0gb9-0900000000-0aa6709c16899e2220862012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0a4i-0900000000-9aa2b9d4aa89e6ac12ab2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0a4i-0900000000-6d98ebfa89f4b8ee1e6b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid EI-B (HITACHI M-80) , Positive-QTOFsplash10-0gb9-2900000000-babed327a6e49c6f7d512012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-014i-0900000000-105f33777cee542cf6df2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-05fr-1900000000-a502792703fa2f2110352012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0a4l-5900000000-037ef32f4c68a5252b922012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0a4i-9800000000-ecd60ac022f5fee1d5ef2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-066u-9300000000-c63f7f792794f3c748a02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid ESI-TOF , Negative-QTOFsplash10-014i-0923211100-7e9f357f7429cff055242017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid ESI-TOF 20V, Negative-QTOFsplash10-014i-0923211100-7e9f357f7429cff055242017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid ESI-TOF , Negative-QTOFsplash10-0a4i-0429110000-57f8760ce65d48cdc01f2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid ESI-TOF 10V, Negative-QTOFsplash10-0a4i-0429110000-57f8760ce65d48cdc01f2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid ESI-TOF , Negative-QTOFsplash10-014i-0923211100-7e9f357f7429cff055242017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid ESI-TOF 20V, Negative-QTOFsplash10-0a4i-0900000000-8e112ffa4dcc7c08b0fd2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid ESI-TOF , Negative-QTOFsplash10-0a4i-0429110000-57f8760ce65d48cdc01f2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid ESI-TOF 10V, Negative-QTOFsplash10-0uxr-0900000000-29a2674dccd1fa478bd52017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-105f33777cee542cf6df2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillic acid LC-ESI-QQ , negative-QTOFsplash10-05fr-1900000000-c4ce596998934098267b2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillic acid 10V, Positive-QTOFsplash10-014i-0900000000-342964fa3647815dd1d22016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillic acid 20V, Positive-QTOFsplash10-0uxr-0900000000-f16c365899f9d95733d32016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillic acid 40V, Positive-QTOFsplash10-0zfs-5900000000-e5593db0a935e1534bc62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillic acid 10V, Negative-QTOFsplash10-014i-0900000000-6a1a2db582acd95348ea2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillic acid 20V, Negative-QTOFsplash10-0600-0900000000-eda6cfe601d63ed00f8d2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillic acid 40V, Negative-QTOFsplash10-0a4i-6900000000-b2c1e3f6b255e94a10af2016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 1D NMR13C NMR Spectrum (1D, 500 MHz, DMSO, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.8 (2.0-8.1) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.099-8.712 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.272 +/- 0.036 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.248 +/- 0.026 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.295 +/- 0.036 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.314 +/- 0.043 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.255 +/- 0.024 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.245 +/- 0.027 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.229 +/- 0.024 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.901 +/- 0.71 uMAdult (>18 years old)Male
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal		 details
FecesDetected and Quantified5.828 +/- 3.0925 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified6.423 +/- 13.857 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified6.542 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified6.661 +/- 4.996 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified2.878 (2.290-4.805) nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified11.2 +/- 3.2 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.43 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.0750-19.200 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified6.991 +/- 3.942 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified1.6 (0.6-3.3) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.596 +/- 0.131 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified0.855 +/- 0.512 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified1.0 (0.0-2.5) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.574 +/- 0.184 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)		 details
UrineDetected and Quantified3.45 +/- 1.002 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID414
FooDB IDFDB000846
KNApSAcK IDC00002682
Chemspider ID8155
KEGG Compound IDC06672
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVanillic acid
METLIN ID5471
PubChem Compound8468
PDB IDNot Available
ChEBI ID30816
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000172
Good Scents IDrw1051611
References
Synthesis ReferencePearl, Irwin A. Reactions of vanillin and its derived compounds. I. The reaction of vanillin with silver oxide. Journal of the American Chemical Society (1946), 68 429-32.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Muskiet FA, Groen A: Urinary excretion of conjugated homovanillic acid, 3,4-dihydroxyphenylacetic acid, p-hydroxyphenylacetic acid, and vanillic acid by persons on their usual diet and patients with neuroblastoma. Clin Chem. 1979 Jul;25(7):1281-4. [PubMed:455649 ]
  2. Ebinger G, Verheyden R: On the occurence of vanillic acid in human brain and cerebrospinal fluid. J Neurol. 1976 Apr 23;212(2):133-8. [PubMed:57225 ]
  3. Lee BL, New AL, Kok PW, Ong HY, Shi CY, Ong CN: Urinary trans,trans-muconic acid determined by liquid chromatography: application in biological monitoring of benzene exposure. Clin Chem. 1993 Sep;39(9):1788-92. [PubMed:8375048 ]
  4. Dhananjaya BL, Nataraju A, Rajesh R, Raghavendra Gowda CD, Sharath BK, Vishwanath BS, D'Souza CJ: Anticoagulant effect of Naja naja venom 5'nucleotidase: demonstration through the use of novel specific inhibitor, vanillic acid. Toxicon. 2006 Sep 15;48(4):411-21. Epub 2006 Jul 7. [PubMed:16899266 ]
  5. Achterholt S, Priefert H, Steinbuchel A: Identification of Amycolatopsis sp. strain HR167 genes, involved in the bioconversion of ferulic acid to vanillin. Appl Microbiol Biotechnol. 2000 Dec;54(6):799-807. [PubMed:11152072 ]
  6. Overhage J, Priefert H, Steinbuchel A: Biochemical and genetic analyses of ferulic acid catabolism in Pseudomonas sp. Strain HR199. Appl Environ Microbiol. 1999 Nov;65(11):4837-47. [PubMed:10543794 ]
  7. Plaggenborg R, Steinbuchel A, Priefert H: The coenzyme A-dependent, non-beta-oxidation pathway and not direct deacetylation is the major route for ferulic acid degradation in Delftia acidovorans. FEMS Microbiol Lett. 2001 Nov 27;205(1):9-16. doi: 10.1111/j.1574-6968.2001.tb10918.x. [PubMed:11728709 ]
  8. Venturi V, Zennaro F, Degrassi G, Okeke BC, Bruschi CV: Genetics of ferulic acid bioconversion to protocatechuic acid in plant-growth-promoting Pseudomonas putida WCS358. Microbiology. 1998 Apr;144 ( Pt 4):965-73. doi: 10.1099/00221287-144-4-965. [PubMed:9579070 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Vanillic acid → 6-(4-carboxy-2-methoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Vanillic acid → 3,4,5-trihydroxy-6-(4-hydroxy-3-methoxybenzoyloxy)oxane-2-carboxylic aciddetails
Enzyme Details
2. Glycine N-acyltransferase
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
Vanillic acid → Vanilloylglycinedetails
Enzyme Details
3. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Vanillic acid → Vanillic acid 4-O-sulfatedetails