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

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CHEBI:25682 - N^ω,N'^ω-dimethyl-L-arginine

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ChEBI ID	CHEBI:25682
ChEBI Name	N^ω,N'^ω-dimethyl-L-arginine
Stars
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
Secondary ChEBI ID	CHEBI:39780
Last Modified	25 November 2019
Downloads	Molfile

Formula	C8H18N4O2
Net Charge	0
Average Mass	202.258
Monoisotopic Mass	202.14298
SMILES	C/N=C(/NC)NCCC[C@H](N)C(=O)O
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

Roles Classification

Chemical Roles:	Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid). Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:	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 Relation(s)
	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 Relation(s)
	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	Source
(2S)-2-amino-5-(N',N''-dimethylcarbamimidamido)pentanoic acid	IUPAC
N,N'-Dimethylarginine	ChemIDplus
N(G1),N(G2)-Dimethylarginine	ChemIDplus
(S)-2-amino-5-(N',N''-dimethylguanidino)pentanoic acid	ChEBI
Guanidino-N(1),N(2)-dimethylarginine	ChemIDplus
N5-((methylamino)(methylimino)methyl)-L-ornithine	ChemIDplus

Manual Xrefs	Databases
2MR	PDBeChem
DB02302	DrugBank
HMDB0003334	HMDB

Registry Numbers	Sources
Beilstein:7973080	Beilstein
Reaxys:7973080	Reaxys
CAS:30344-00-4	ChemIDplus

Citations