Details of Metabolite

General Information of MET (ID: META00508)
Name Symmetric dimethylarginine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2S)-2-Amino-5-(n',n''-dimethylcarbamimidamido)pentanoic acid, (S)-2-Amino-5-(n',n''-dimethylguanidino)pentanoic acid, 'Guanidino-N(1),N(2)-dimethylarginine; N(3),N(4)-Dimethylarginine; N(g1),N(g2)-Dimethylarginine', N,N'-dimethylarginine, 'N(3),N(4)-Dimethyl-L-arginine; N5-((Methylamino)(methylimino)methyl)-L-ornithine', N(5)-(N,N'-dimethylamidino)-L-ornithine, N(5)-(N,N'-dimethylcarbamimidoyl)-L-ornithine, 'N(5)-[Bis(methylamino)methylene]-L-ornithine', N(g),N'(g)-dimethyl-L-arginine, N(g),N'(g)-dimethylarginine, 'SDMA', (2S)-2-Amino-5-(n',n''-dimethylcarbamimidamido)pentanoate, (S)-2-Amino-5-(n',n''-dimethylguanidino)pentanoate, N5-(N,N'-dimethylamidino)-L-ornithine, 'N5-[Bis(methylamino)methylene]-L-ornithine', NG,N'G-dimethyl-L-arginine, NG,N'G-dimethylarginine, NG,NG'-dimethylarginine, Omega-N(g),n'(g)-dimethylarginine, 'SDMA arginine
Source Endogenous;Food;Drug;Toxins/Pollutant
Structure Type   Amino acids, peptides, and analogues  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Amino acids, peptides, and analogues
PubChem CID
169148
HMDB ID
HMDB0003334
Formula
C8H18N4O2
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
DrugBank ID
DB02302
ChEBI ID
25682
FooDB ID
FDB000509
ChemSpider ID
147942
METLIN ID
6891
Physicochemical Properties Molecular Weight 202.25 Topological Polar Surface Area 99.7
XlogP -3.7 Complexity 206
Heavy Atom Count 14 Rotatable Bond Count 7
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 4
Function
Symmetric dimethylarginine (SDMA) is an endogenously produced inhibitor of nitric oxide synthase (EC-Number 1.14.13.39). However, elevated levels of SDMA occur in patients with vascular disease, especially suffering end-stage renal disease. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Amino acid/polyamine transporter (AAPT)
            Solute carrier family 7 member 1 (SLC7A1) 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 SLC7A1
                      Induced Change Symmetric dimethylarginine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLC7A1 leads to the decrease of symmetric dimethylarginine levels compared with control group.
      GPCR secretin (GPCR-2)
            Glucagon receptor (GCGR) 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 Gcgr
                      Induced Change Symmetric dimethylarginine concentration: increase (FC = 1.7)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Type 2 diabetes mellitus [ICD-11: 5A11]
                      Details It is reported that knockout of GCGR leads to the increase of symmetric dimethylarginine levels compared with control group.
References
1 Interaction of the cardiovascular risk marker asymmetric dimethylarginine (ADMA) with the human cationic amino acid transporter 1 (CAT1). J Mol Cell Cardiol. 2012 Sep;53(3):392-400.
2 Polyomic profiling reveals significant hepatic metabolic alterations in glucagon-receptor (GCGR) knockout mice: implications on anti-glucagon therapies for diabetes. BMC Genomics. 2011 Jun 1;12:281.

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