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CHEBI:17929 - Nω,Nω-dimethyl-L-arginine

Default Structure
ChEBI IDCHEBI:17929
ChEBI NameNω,Nω-dimethyl-L-arginine
Stars
ASCII NameN(omega),N(omega)-dimethyl-L-arginine
DefinitionA L-arginine derivative having two methyl groups both attached to the primary amino moiety of the guanidino group.
Secondary ChEBI IDsCHEBI:7432, CHEBI:12680, CHEBI:21908, CHEBI:25683, CHEBI:41833
Last Modified30 October 2015
DownloadsMolfile
FormulaC8H18N4O2
Net Charge0
Average Mass202.258
Monoisotopic Mass202.14298
SMILESCN(C)C(=N)NCCC[C@H](N)C(=O)O
InChIInChI=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
InChIKeyYDGMGEXADBMOMJ-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)
Nω,Nω-dimethyl-L-arginine (CHEBI:17929) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
Nω,Nω-dimethyl-L-arginine (CHEBI:17929) is a L-arginine derivative (CHEBI:83965)
Nω,Nω-dimethyl-L-arginine (CHEBI:17929) is a dimethylarginine (CHEBI:86468)
Nω,Nω-dimethyl-L-arginine (CHEBI:17929) is a guanidines (CHEBI:24436)
Nω,Nω-dimethyl-L-arginine (CHEBI:17929) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
Nω,Nω-dimethyl-L-arginine (CHEBI:17929) is conjugate base of Nω,Nω-dimethyl-L-argininium(1+) (CHEBI:58326)
Incoming Relation(s)
Nω,Nω-dimethyl-L-argininium(1+) (CHEBI:58326) is conjugate acid of Nω,Nω-dimethyl-L-arginine (CHEBI:17929)
Nω,Nω-dimethyl-L-arginine residue (CHEBI:61896) is substituent group from Nω,Nω-dimethyl-L-arginine (CHEBI:17929)
IUPAC Names 
(2S)-2-amino-5-{[(dimethylamino)(imino)methyl]amino}pentanoic acid
(2S)-2-amino-5-(N',N'-dimethylcarbamimidamido)pentanoic acid
N5-[(dimethylamino)(imino)methyl]-L-ornithine
N5-(N,N-dimethylcarbamimidoyl)-L-ornithine
Synonyms  Source
ADMAHMDB
asymmetric dimethylarginineChEBI
N,N-dimethylarginineChemIDplus
N5-((dimethylamino)iminomethyl)-L-ornithineChemIDplus
NG1,NG1-dimethylarginineChemIDplus
NG-dimethylarginineChemIDplus
Manual XrefsDatabases
C03626KEGG COMPOUND
DA2PDBeChem
DB01686DrugBank
Registry NumbersSources
Beilstein:2261521Beilstein
CAS:30315-93-6ChemIDplus
CAS:30315-93-6KEGG COMPOUND