N(omega),N'(omega)-dimethyl-L-arginine (CHEBI:25682)

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

ChEBI ID	CHEBI:25682

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

Definition	A L-arginine derivative having two methyl groups at the N^ω- and N'^ω-positions

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

Secondary ChEBI IDs	CHEBI:39780

Supplier Information

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Formula

C8H18N4O2

Net Charge

Average Mass

202.25410

Monoisotopic Mass

202.14298

InChI

InChI=1S/C8H18N4O2/c1-10-8(11-2)12-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H,13,14)(H2,10,11,12)/t6-/m0/s1

InChIKey

HVPFXCBJHIIJGS-LURJTMIESA-N

SMILES

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

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:25682) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908) N^ω,N'^ω-dimethyl-L-arginine (CHEBI:25682) is a L-arginine derivative (CHEBI:83965) N^ω,N'^ω-dimethyl-L-arginine (CHEBI:25682) is a dimethylarginine (CHEBI:86468) N^ω,N'^ω-dimethyl-L-arginine (CHEBI:25682) is a guanidines (CHEBI:24436) N^ω,N'^ω-dimethyl-L-arginine (CHEBI:25682) is a non-proteinogenic L-α-amino acid (CHEBI:83822) N^ω,N'^ω-dimethyl-L-arginine (CHEBI:25682) is conjugate base of N^ω,N^'ω-dimethyl-L-argininium(1+) (CHEBI:197308) N^ω,N'^ω-dimethyl-L-arginine (CHEBI:25682) is tautomer of N^ω,N'^ω-dimethyl-L-arginine zwitterion (CHEBI:61914)

Incoming	N^ω,N^'ω-dimethyl-L-argininium(1+) (CHEBI:197308) is conjugate acid of N^ω,N'^ω-dimethyl-L-arginine (CHEBI:25682) N^ω,N'^ω-dimethyl-L-argininyl residue (CHEBI:61916) is substituent group from N^ω,N'^ω-dimethyl-L-arginine (CHEBI:25682) N^ω,N'^ω-dimethyl-L-arginine zwitterion (CHEBI:61914) is tautomer of N^ω,N'^ω-dimethyl-L-arginine (CHEBI:25682)

IUPAC Name

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

Synonyms	Sources
(2S)-2-amino-5-(N',N''-dimethylcarbamimidamido)pentanoic acid	IUPAC
(S)-2-amino-5-(N',N''-dimethylguanidino)pentanoic acid	ChEBI
Guanidino-N(1),N(2)-dimethylarginine	ChemIDplus
N(G1),N(G2)-Dimethylarginine	ChemIDplus
N,N'-Dimethylarginine	ChemIDplus
N³,N⁴-dimethyl-L-arginine	ChEBI
N³,N⁴-dimethylarginine	ChEBI
N5-((methylamino)(methylimino)methyl)-L-ornithine	ChemIDplus
N⁵-(N,N'-dimethylamidino)-L-ornithine	ChEBI
N⁵-(N,N'-dimethylcarbamimidoyl)-L-ornithine	ChEBI
N⁵-[bis(methylamino)methylene]-L-ornithine	ChEBI
N^G,N'^G-dimethyl-L-arginine	ChEBI
N^G,N'^G-dimethylarginine	ChEBI
SDMA	HMDB
symmetric dimethylarginine	ChEBI

Last Modified

25 November 2019