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Asymmetric dimethylarginine

Asymmetric dimethylarginine structure

Asymmetric dimethylarginine 

structure
  • CAS No:

    30315-93-6

  • Formula:

    C8H18N4O2

  • Chemical Name:

    Asymmetric dimethylarginine

  • Synonyms:

    L-Ornithine,N5-[(dimethylamino)iminomethyl]-;Ornithine,N5-(N,N-dimethylamidino)-,L-;N5-[(Dimethylamino)iminomethyl]-L-ornithine;NG,NG-Dimethylarginine;Dimethyl-L-arginine;L-NG,NG-Dimethylarginine;Asymmetric dimethylarginine;ADMA;(S)-2-Amino-5-(3,3-dimethylguanidino)pentanoic acid;(2S)-2-Amino-5-[[amino(dimethylamino)methylidene]amino]pentanoic acid;32747-09-4

Description

Asymmetric dimethylarginine is an endogenous inhibitor of nitric oxide synthase (NOS), and functions as a marker of endothelial dysfunction in a number of pathological states.


Solid


N(omega),N(omega)-dimethyl-L-arginine is a L-arginine derivative having two methyl groups both attached to the primary amino moiety of the guanidino group. It has a role as an EC 1.14.13.39 (nitric oxide synthase) inhibitor. It is a non-proteinogenic L-alpha-amino acid, a member of guanidines, a L-arginine derivative and a dimethylarginine. It is a conjugate base of a N(omega),N(omega)-dimethyl-L-argininium(1+).|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 which 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 Basic Attributes

202.258

202.25

2925290090

Characteristics

105

-3.6

Solid

1.239g/cm3

195 - 197 °C

179.115°C

143.5 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|141 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine]|143.9 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|157.2 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

Drug Information

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.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

asymmetric dimethylarginine

Computed Properties

Molecular Weight:202.25
XLogP3:-3.6
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:202.14297583
Monoisotopic Mass:202.14297583
Topological Polar Surface Area:105
Heavy Atom Count:14
Complexity:215
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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