General Information of MET (ID: META00782)
Name Vanillic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
3-Methoxy-4-hydroxybenzoate; 3-Methoxy-4-hydroxybenzoic acid; 4 Hydroxy 3 methoxybenzoic acid; 4-Hydroxy-3-methoxy-benzoate; 4-Hydroxy-3-methoxy-benzoic acid; 4-Hydroxy-3-methoxybenzoate; 4-Hydroxy-3-methoxybenzoic acid; 4-Hydroxy-m-anisate; 4-Hydroxy-m-anisic acid; Acid, 4-hydroxy-3-methoxybenzoic; Acid, p-hydroxy-m-methoxy-benzoic; Acid, vanillic; Acide vanillique; Protocatechuic acid 3-methyl ester; Vanillate; Vanillic acid; p Hydroxy m methoxy benzoic acid; p-Hydroxy-m-methoxy-benzoic acid; p-Vanillate; p-Vanillic acid
Source Food;Yeast Metabolite;Food additives;TCM Ingredients;Ferulic;acid;Microbial; Herbal Ingredients In-Vivo Metabolism
Structure Type   Benzoic acids and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Benzenoids
Benzene and substituted derivatives
Benzoic acids and derivatives
PubChem CID
8468
HMDB ID
HMDB0000484
Formula
C8H8O4
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C06672
ChEBI ID
30816
FooDB ID
FDB000846
ChemSpider ID
8155
METLIN ID
5471
Physicochemical Properties Molecular Weight 168.15 Topological Polar Surface Area 66.8
XlogP 1.4 Complexity 168
Heavy Atom Count 12 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Function
Vanillic 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. Vanillic acid is a microbial metabolite found in Amycolatopsis, Delftia, and Pseudomonas.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transcription factor (TF)
            R2R3-MYB (AN2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of AN2
                      Induced Change Vanillic acid concentration: increase (FC = 10.40)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the increase of vanillic acid levels compared with control group.
References
1 Comprehensive Influences of Overexpression of a MYB Transcriptor Regulating Anthocyanin Biosynthesis on Transcriptome and Metabolome of Tobacco Leaves. Int J Mol Sci. 2019 Oct 16;20(20):5123.

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