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Bovine Rumen Metabolome Database



Showing metabocard for Dimethyl-L-arginine (RMDB01539)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-07-24 14:29:17
Accession Number RMDB01539
Common Name Dimethyl-L-arginine
Description Asymmetric dimethylarginine (ADMA) is a naturally occurring chemical found in blood plasma. It is a metabolic by-product of continual protein modification processes in the cytoplasm of all human cells. It is closely related to L-arginine, a conditionally-essential amino acid. ADMA interferes with L-arginine in the production of nitric oxide, a key chemical to endothelial and hence cardiovascular health. Asymmetric dimethylarginine is created in protein methylation, a common mechanism of post-translational protein modification. This reaction is catalyzed by an enzyme set called S-adenosylmethionine protein N-methyltransferases (protein methylases I and II). The methyl groups transferred to create ADMA are derived from the methyl group donor S-adenosylmethionine, an intermediate in the metabolism of homocysteine. (Homocysteine is an important blood chemical, because it is also a marker of cardiovascular disease). After synthesis, ADMA migrates into the extracellular space and thence into blood plasma. Asymmetric dimethylarginine is measured using high performance liquid chromatography.
Synonyms
  1. 2-amino-5-(amino-dimethylamino-methylidene)amino-pentanoate
  2. 2-amino-5-(amino-dimethylamino-methylidene)amino-pentanoic acid
  3. ADMA
  4. NG,NG-Dimethyl-L-arginine
  5. NG,NG-dimethylarginine
  6. NG-dimethylarginine
  7. Asymmetric dimethylarginine
Chemical IUPAC Name (2S)-2-amino-5-[(amino-dimethylamino-methylidene)amino]pentanoic acid
Chemical Formula C8H18N4O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Amino Acids
Sub Class
  • NA
Family
  • Mammalian_Metabolite
Species
  • primary amine; primary aliphatic amine (alkylamine); carboxylic acid; guanidine; alpha-aminoacid
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application
Source
  • Endogenous
Average Molecular Weight 202.254
Monoisotopic Molecular Weight 202.142975
Isomeric SMILES CN(C)C(=N)NCCC[C@H](N)C(O)=O
Canonical SMILES CN(C)C(=N)NCCCC(N)C(O)=O
KEGG Compound ID C03626 Link Image
BioCyc ID CPD-596 Link Image
BiGG ID Not Available
Wikipedia Link Asymmetric dimethylarginine Link Image
METLIN ID 6309 Link Image
PubChem Compound 123831 Link Image
PubChem Substance 6410 Link Image
ChEBI ID 17929 Link Image
CAS Registry Number 102783-24-4
InChI Identifier InChI=1/C8H18N4O2/c1-12(2)8(10)11-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14)/t6-/m0/s1
Synthesis Reference Not Available
Melting Point (Experimental) 195-197 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1.52 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -3.15 [Predicted by ALOGPS]; -2.6 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID 7NSE Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from LogP)
Biofluid Location
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 0.33 +/- 0.14 uM
Age N/A
Sex Female
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image