Details of Metabolite

General Information of MET (ID: META00265)
Name Adenylsuccinic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
Adenylosuccinate; Adenylosuccinic acid; Adenylsuccinic acid; N-[9-(5-O-Phosphono-beta-D-ribofuranosyl)-9H-purin-6-yl]-L-aspartic acid; N6-(1,2-Dicarboxyethyl)AMP; Succinyladenosine monophosphoric acid
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food
Structure Type   Biphenyls and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Benzenoids
Benzene and substituted derivatives
Biphenyls and derivatives
PubChem CID
447145
HMDB ID
HMDB0000536
Formula
C14H18N5O11P
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
C03794
DrugBank ID
DB04418
FooDB ID
FDB022101
ChemSpider ID
394323
Physicochemical Properties Molecular Weight 463.29 Topological Polar Surface Area 247
XlogP -3.2 Complexity 725
Heavy Atom Count 31 Rotatable Bond Count 9
Hydrogen Bond Donor Count 7 Hydrogen Bond Acceptor Count 15
Function
Adenylsuccinic acid, also known as adenylosuccinate or aspartyl adenylate, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Adenylsuccinic acid is a strong basic compound (based on its pKa). Within humans, adenylsuccinic acid participates in a number of enzymatic reactions. In particular, adenylsuccinic acid can be converted into fumaric acid through its interaction with the enzyme adenylosuccinate lyase. In addition, adenylsuccinic acid can be biosynthesized from inosinic acid and L-aspartic acid which is catalyzed by the enzyme adenylosuccinate synthetase. Adenylosuccinate is an intermediate in the interconversion of the purine nucleotides inosine monophosphate (IMP) and adenosine monophosphate (AMP). GTP is used instead of adenosine triphosphate (ATP), so the reaction is not dependent on its products. The enzyme adenylosuccinate synthase carries out the reaction by the addition of aspartate to IMP and requires the input of energy from a phosphoanhydride bond in the form of guanosine triphosphate (GTP). Adenylsuccinic acid is a substrate of the enzyme adenylosuccinase (EC 4.3.2.2) in purine metabolism. The accumulation of adenylsuccinic acid in bodily fluids occurs due to a deficiency of adenylosuccinase.
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 Adenylsuccinic 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 adenylsuccinic acid levels compared with control group.
            Sulfatase sulf-1 (SULF1) 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 Knockdown (shRNA) of SULF1
                      Induced Change Adenylsuccinic acid concentration: decrease (FC = 0.51 / 0.52)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the decrease of adenylsuccinic acid levels compared with control group.
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) 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 [3]
                      Introduced Variation Knockout of TP53
                      Induced Change Adenylsuccinic acid concentration: decrease (Log2 FC=0.57)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the decrease of adenylsuccinic 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.
2 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
3 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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