Details of Metabolite

General Information of MET (ID: META00163)
Name Homovanillic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(4-Hydroxy-3-methoxyphenyl)acetate; (4-Hydroxy-3-methoxyphenyl)acetic acid; 3 Methoxy 4 hydroxyphenylacetic acid; 3-Methoxy-4-hydroxy-phenylacetic acid; 3-Methoxy-4-hydroxyphenylacetate; 3-Methoxy-4-hydroxyphenylacetic acid; 4 Hydroxy 3 methoxyphenylacetic acid; 4-Hydroxy 3-methoxyphenylacetic acid; 4-Hydroxy-3-methoxybenzeneacetate; 4-Hydroxy-3-methoxybenzeneacetic acid; 4-Hydroxy-3-methoxyphenylacetic acid; Acid, 3-methoxy-4-hydroxyphenylacetic; Acid, 4-hydroxy-3-methoxyphenylacetic; HVA; Homovanilate; Homovanilic acid; Homovanillate; Homovanillic acid; Homovanillinic acid; Vanilacetate; Vanilacetic acid; Vanillacetate; Vanillacetic acid
Source Endogenous;Yeast Metabolite;Food;TCM Ingredients;Microbial
Structure Type   Methoxyphenols  (Click to Show/Hide the Complete Structure Type Hierarchy)
Benzenoids
Phenols
Methoxyphenols
PubChem CID
1738
HMDB ID
HMDB0000118
Formula
C9H10O4
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
C05582
ChEBI ID
545959
FooDB ID
FDB001783
ChemSpider ID
1675
METLIN ID
971
Physicochemical Properties Molecular Weight 182.17 Topological Polar Surface Area 66.8
XlogP 0.4 Complexity 181
Heavy Atom Count 13 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Function
Homovanillic acid is a dopamine metabolite occurring in human biofluids. A high proportion of patients with neuroblastoma excrete increased amounts of it in their urine. Homovanillic acid is a major catecholamine metabolite. It is used as a reagent to detect oxidative enzymes. Homovanillic acid is found to be associated with aromatic L-amino acid decarboxylase deficiency, celiac disease, growth hormone deficiency, and sepiapterin reductase deficiency, which are inborn errors of metabolism. Homovanillic acid is also a metabolite of Bifidobacterium and of flavonoids.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      GPCR glutamate (GPCR-3)
            Glutamate receptor mGLU2 (mGluR2) 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 Knockout of Grm2
                      Induced Change Homovanillic acid concentration: decrease (FC = 0.78)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of mGlu2/3 leads to the decrease of homovanillic acid levels compared with control group.
            Glutamate receptor mGLU3 (mGluR3) 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 Knockout of Grm3
                      Induced Change Homovanillic acid concentration: decrease (FC = 0.78)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of mGlu2/3 leads to the decrease of homovanillic acid levels compared with control group.
      GPCR rhodopsin (GPCR-1)
            Dopamine D4 receptor (D4R) 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 [2]
                      Introduced Variation Knockout of Drd4
                      Induced Change Homovanillic acid concentration: decrease (FC = 0.60)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of DRD4 leads to the decrease of homovanillic acid levels compared with control group.
      Neuropeptide Y (NPY)
            Neuropeptide Y (NPY) Click to Show/Hide the Full List of Regulating Pair(s):   2 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Antagonist ([D-Trp32]NPY) of Npy
                      Induced Change Homovanillic acid concentration: increase (FC = 2.20)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that antagonist [D-Trp32]NPY of Npy leads to the increase of homovanillic acid levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Overexpression of Npy
                      Induced Change Homovanillic acid concentration: increase (FC = 3.00)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of Npy leads to the increase of homovanillic acid levels compared with control group.
References
1 Decreased striatal dopamine in group II metabotropic glutamate receptor (mGlu2/mGlu3) double knockout mice. BMC Neurosci. 2013 Sep 22;14:102.
2 Dopamine D4 receptor knockout mice exhibit neurochemical changes consistent with decreased dopamine release. J Neurosci Methods. 2007 Nov 30;166(2):306-14.
3 Effects of neuropeptide Y (NPY) and [D-Trp32]NPY on monoamine and metabolite levels in dialysates from rat hypothalamus during feeding behavior. Neuropeptides. 1996 Aug;30(4):391-8.

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