dimethylarginine (ADMA)

Info Variations

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Name: dimethylarginine (ADMA)
Description: An L-arginine derivative having two methyl groups both attached to the primary amino moiety of the guanidino group. Asymmetric dimethylarginine (ADMA) is a naturally occurring chemical found in blo... od 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. (CHEBI:17929; HMDB0001539; DrugBank ID:DB01686)

Age group comparisons
PMID	Age/Age interval, Gender	Value (unit of measurement)	Method	Sample

Linear regression
PMID	Age/Age interval, Gender	Value (unit of measurement)	Method	Sample
23838602	Age [17–85], Gender ⚥	-0.005 (β)	UHPLC/MS/MS	serum + plasma

log2 ratio/log2(FC)
PMID	Age/Age interval, Gender	Value (unit of measurement)	Method	Sample

Synonym:

NG,NG-Dimethyl-L-arginine; NG-dimethylarginine; N5-((dimethylamino)iminomethyl)-L-ornithine; guanidino-N,N-dimethylarginine;asymmetric dimethylarginine
Chemical Formula:

C8H18N4O2
Exact Mass g/mol:

202.1430000
Systematic name:

N5-[(dimethylamino)(imino)methyl]-L-ornithine; N5-(N,N-dimethylcarbamimidoyl)-L-ornithine; (2S)-2-amino-5-{[(dimethylamino)(imino)methyl]amino}pentanoic acid;(2S)-2-amino-5-[[amino(dimethylamino)methylidene]amino]pentanoic acid; (2S)-2-amino-5-(N',N'-dimethylcarbamimidamido)pentanoic acid
SMILES:

CN(C)C(=NCCC[C@@H](C(=O)O)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
InChI Key:

YDGMGEXADBMOMJ-LURJTMIESA-N
CAS number:

30315-93-6; 63937-30-4

Metabolite location:

Human organism, Body part, Human body biofluids, Biofluid tissues, Blood, Plasma, Serum, Cerebrospinal fluid, Urine, Organ, Kidney, Liver, Tissue, Cellular (general class), Subcellular, Cytoplasm, Mitochondria, Excreta material
Metabolite source:

Homo sapiens, endogenous metabolite

Linear regression

Method: UHPLC/MS/MS

Sample: serum + plasma

PMID: 23838602

β = -0.005 (y = βx + α)

p-value < 0.05