(2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid

• ChemBase ID: 1460
• Molecular Formular: C8H18N4O2
• Molecular Mass: 202.25412
• Monoisotopic Mass: 202.14297584
• SMILES: CN(C)/C(=N/CCC[C@H](N)C(=O)O)/N
• Canonical SMILES: OC(=O)[C@H](CCC/N=C(/N(C)C)\N)N
• InChI: InChI=1S/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
• InChIKey: YDGMGEXADBMOMJ-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid
• IUPAC Traditional name: N,N-dimethylarginine
• Synonyms: ADMA; Asymmetric dimethylarginine; Dimethyl-l-arginine; Guanidino-n,n-dimethylarginine; Lopac-D-4268; N(5)-((Dimethylamino)iminomethyl)-L-ornithine; N(5)-[(dimethylamino)(imino)methyl]-L-ornithine; N(G1),N(G1)-Dimethylarginine; N(g),N(g)-dimethyl-l-arginine; N(g),N(g)-dimethylarginine; N(g)-dimethylarginine; N(omega),N(omega)-dimethyl-l-arginine; NG,NG-dimethyl-l-arginine; N,N-dimethylarginine

Database IDs

• CAS Number: 102783-24-4
• PubChem SID: 46508091; 160964919
• PubChem CID: 123831

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.5392625
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -5.5796237
• LogD (pH = 7.4): -4.3525457
• Log P: -2.672998
• Molar Refractivity: 53.6996 cm^3
• Polarizability: 20.554567 Å^3
• Polar Surface Area: 104.94 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.13
• LOG S: -1.48
• Solubility (Water): 6.77e+00 g/l

DETAILS

DrugBank - DB01686

• Drug Groups: experimental
• 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. [Wikipedia]
• Pharmacology: Asymmetric dimethylarginine (ADMA), an endogenous inhibitor of nitric oxide synthase, is formed by methylation of arginine residues in proteins and released after proteolysis. In this reaction, S-adenosylmethionine is methyldonor and S-adenosylhomocysteine the demethylated product. ADMA and homocysteine are thus biochemically linked. Both plasma homocysteine and ADMA concentrations are increased in patients with renal dysfunction, probably as a result of an impairment in their metabolic, but not urinary, clearance. Hyperhomocysteinemia has been associated with an increased risk of cardiovascular disease in end-stage renal disease, especially in patients without malnutrition and inflammation. Also, plasma ADMA levels have been associated with cardiovascular disease in renal failure patients. Both homocysteine and ADMA are thought to mediate their adverse vascular effects by impairing endothelial, nitric oxide-dependent function resulting in decreased vasodilatation, increased smooth muscle cell proliferation, platelet dysfunction and increased monocyte adhesion.
• Affected Organisms: Humans and other mammals
• References: van Guldener C, Nanayakkara PW, Stehouwer CD: Review: Homocysteine and asymmetric dimethylarginine (ADMA): biochemically linked but differently related to vascular disease in chronic kidney disease. Clin Chem Lab Med. 2007 Oct 15;. [Pubmed]
• External Links: Wikipedia

REFERENCES

• van Guldener C, Nanayakkara PW, Stehouwer CD: Review: Homocysteine and asymmetric dimethylarginine (ADMA): biochemically linked but differently related to vascular disease in chronic kidney disease. Clin Chem Lab Med. 2007 Oct 15;. Pubmed