Details of Metabolite

General Information of MET (ID: META00238)
Name Vanillylmandelic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(4-Hydroxy-3-methoxyphenyl)glycolate; (4-Hydroxy-3-methoxyphenyl)glycolic acid; 2-Phenyllactic acid; 3-Methoxy-4-hydroxy-mandelic acid; 3-Methoxy-4-hydroxymandelate; 3-Methoxy-4-hydroxymandelic acid; 3-Methoxy-4-hydroxyphenylhydroxyacetate; 3-Methoxy-4-hydroxyphenylhydroxyacetic acid', 4'-Hydroxy-3'-methoxymandelate, 4'-Hydroxy-3'-methoxymandelic acid, '4-Hydroxy 3-methoxymandelic acid; 4-Hydroxy-3-methoxy-DL-mandelate; 4-Hydroxy-3-methoxy-DL-mandelic acid; 4-Hydroxy-3-methoxy-mandelate; 4-Hydroxy-3-methoxy-mandelic acid; 4-Hydroxy-3-methoxymandelate; 4-Hydroxy-3-methoxymandelic acid; Atrolactic acid; Atrolactic acid monosodium salt, (S)-isomer; Atrolactic acid, (+-)-isomer; DL-3-Methoxy-4-hydroxymandelate; DL-3-Methoxy-4-hydroxymandelic acid; DL-4-Hydroxy-3-methoxymandelate; DL-4-Hydroxy-3-methoxymandelic acid; DL-Vanillomandelate; DL-Vanillomandelic acid; DL-Vanillylmandelate; DL-Vanillylmandelic acid; HMMA; Hydroxymethoxymandelic acid; Hydroxymethylmandelic acid; Lopac-H-0131; VMA; VMA CPD; Vainillylmandelic acid; Vanillinmandelate; Vanillinmandelic acid; Vanillomandelate; Vanillomandelic acid; Vanillyl-mandelic acid; Vanillylmandelate; Vanillylmandellic acid; Vanillymandelic acid; Vanilmandelate; Vanilmandelic acid; Vanilylmandelic acid; Vanyl-mandelic acid; Vanylmandelic acid
Source Endogenous;Escherichia Coli Metabolite;Food
Structure Type   Methoxyphenols  (Click to Show/Hide the Complete Structure Type Hierarchy)
Benzenoids
Phenols
Methoxyphenols
PubChem CID
736172
HMDB ID
HMDB0000291
Formula
C9H10O5
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
C05584
ChEBI ID
1127735
FooDB ID
FDB021931
ChemSpider ID
643307
METLIN ID
697
Physicochemical Properties Molecular Weight 198.17 Topological Polar Surface Area 87
XlogP -0.2 Complexity 205
Heavy Atom Count 14 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Function
Vanillylmandelic acid is one of the products of the catabolism of catecholamines (epinephrine, norepinephrine and dopamine). High levels of vanillylmandelic acid can indicate an adrenal gland tumor (pheochromocytoma) or another type of tumor that produces catecholamines (WebMD). Vanillylmandelic acid is found to be associated with aromatic L-amino acid decarboxylase deficiency, which is an inborn error of metabolism.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Leukotriene-C4 hydrolase (GGT1) 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 Knockdown (siRNA) of GGT1
                      Induced Change Vanillylmandelic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Renal cell carcinoma [ICD-11: 2C90]
                      Details It is reported that knockdown of GGT1 leads to the increase of vanillylmandelic acid levels compared with control group.
References
1 Impairment of gamma-glutamyl transferase 1 activity in the metabolic pathogenesis of chromophobe renal cell carcinoma. Proc Natl Acad Sci U S A. 2018 Jul 3;115(27):E6274-E6282.

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