N(omega),N(omega)-dimethyl-L-arginine (CHEBI:17929)

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ChEBI Name	N^ω,N^ω-dimethyl-L-arginine

ChEBI ID	CHEBI:17929

ChEBI ASCII Name	N(omega),N(omega)-dimethyl-L-arginine

Definition	A L-arginine derivative having two methyl groups both attached to the primary amino moiety of the guanidino group.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:41833, CHEBI:7432, CHEBI:12680, CHEBI:21908, CHEBI:25683

Supplier Information

Download	Molfile XML SDF

Formula

C8H18N4O2

Net Charge

Average Mass

202.25428

Monoisotopic Mass

202.14298

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

SMILES

CN(C)C(=N)NCCC[C@H](N)C(O)=O

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	EC 1.14.13.39 (nitric oxide synthase) inhibitor An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).

ChEBI Ontology
Outgoing	N^ω,N^ω-dimethyl-L-arginine (CHEBI:17929) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908) N^ω,N^ω-dimethyl-L-arginine (CHEBI:17929) is a L-arginine derivative (CHEBI:83965) N^ω,N^ω-dimethyl-L-arginine (CHEBI:17929) is a dimethylarginine (CHEBI:86468) N^ω,N^ω-dimethyl-L-arginine (CHEBI:17929) is a guanidines (CHEBI:24436) N^ω,N^ω-dimethyl-L-arginine (CHEBI:17929) is a non-proteinogenic L-α-amino acid (CHEBI:83822) N^ω,N^ω-dimethyl-L-arginine (CHEBI:17929) is conjugate base of N^ω,N^ω-dimethyl-L-argininium(1+) (CHEBI:58326)

Incoming	N^ω,N^ω-dimethyl-L-argininium(1+) (CHEBI:58326) is conjugate acid of N^ω,N^ω-dimethyl-L-arginine (CHEBI:17929) N^ω,N^ω-dimethyl-L-arginine residue (CHEBI:61896) is substituent group from N^ω,N^ω-dimethyl-L-arginine (CHEBI:17929)

IUPAC Names

(2S)-2-amino-5-(N',N'-dimethylcarbamimidamido)pentanoic acid

(2S)-2-amino-5-{[(dimethylamino)(imino)methyl]amino}pentanoic acid

N⁵-(N,N-dimethylcarbamimidoyl)-L-ornithine

N⁵-[(dimethylamino)(imino)methyl]-L-ornithine

Synonyms	Sources
ADMA	HMDB
asymmetric dimethylarginine	ChEBI
guanidino-N,N-dimethylarginine	ChemIDplus
N,N-dimethylarginine	ChemIDplus
N⁵-((dimethylamino)iminomethyl)-L-ornithine	ChemIDplus
NG,NG-Dimethyl-L-arginine	KEGG COMPOUND
NG,NG-DIMETHYL-L-ARGININE	PDBeChem
NG,NG-Dimethyl-L-arginine	KEGG COMPOUND
N^G,N^G-dimethylarginine	ChemIDplus
N^G-dimethylarginine	ChemIDplus
N^G1,N^G1-dimethylarginine	ChemIDplus

Last Modified

30 October 2015