Chemical Component Summary

NameN-OMEGA-NITRO-L-ARGININE
SynonymsNNA
Identifiers(2S)-2-amino-5-[(N-nitrocarbamimidoyl)amino]pentanoic acid
FormulaC6 H13 N5 O4
Molecular Weight219.199
TypeL-PEPTIDE LINKING
Isomeric SMILES[H]/N=C(\NCCC[C@@H](C(=O)O)N)/N[N+](=O)[O-]
InChIInChI=1S/C6H13N5O4/c7-4(5(12)13)2-1-3-9-6(8)10-11(14)15/h4H,1-3,7H2,(H,12,13)(H3,8,9,10)/t4-/m0/s1
InChIKeyMRAUNPAHJZDYCK-BYPYZUCNSA-N

Chemical Details

Formal Charge0
Atom Count28
Chiral Atom Count1
Bond Count27
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB04223 
NameNitroarginine
Groups
  • investigational
  • experimental
DescriptionAn inhibitor of nitric oxide synthetase which has been shown to prevent glutamate toxicity. Nitroarginine has been experimentally tested for its ability to prevent ammonia toxicity and ammonia-induced alterations in brain energy and ammonia metabolites. (Neurochem Res 1995:200(4):451-6)
Synonyms
  • N(gamma)-nitro-L-arginine
  • Ngamma-Nitro-L-arginine
  • Nitroarginine
  • omega-Nitroarginine
  • L-NNA
Categories
  • Amino Acids
  • Amino Acids, Basic
  • Amino Acids, Diamino
  • Amino Acids, Peptides, and Proteins
  • Arginine
CAS number2149-70-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Nitric oxide synthase, endothelialMGNLKSVAQEPGPPCGLGLGLGLGLCGKQGPATPAPEPSRAPASLLPPAP...unknown
Nitric oxide synthase, brainMEDHMFGVQQIQPNVISVRLFKRKVGGLGFLVKERVSKPPVIISDLIRGG...unknown
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL227744
PubChem 135409365, 135453301, 28360916, 440005
ChEMBL CHEMBL227744
ChEBI CHEBI:27960