Structure via PubChem · Public domain (PubChem)
nitroarginine
Sign in to saveAlso known as compound 2 [PMID: 9667974], Nω-nitro-L-arginine, N5-(nitroamidino)-L-ornithine, (+)-NG-nitroarginine, NG-nitro-L-arginine, L-NG-nitroarginine, L-NNA, L-NOARG
Nitroarginine, or '''Nω-nitro--arginine, also known as L-NOARG''', is a nitro derivative of the amino acid arginine. It is an inhibitor of nitric oxide synthase and hence a vasoconstrictor. As such, it finds widespread use as a biochemical tool in the study of nitric oxide and its biological effects.
Chemical data
- Formula
- C6H13N5O4
- Molecular weight
- 219.2 g/mol
- IUPAC name
- (2S)-2-amino-5-[[amino(nitramido)methylidene]amino]pentanoic acid
- SMILES
- C(C[C@@H](C(=O)O)N)CN=C(N)N[N+](=O)[O-]
- InChIKey
- MRAUNPAHJZDYCK-BYPYZUCNSA-N
- XLogP
- -3.6
- Polar surface area
- 160 Ų
- H-bond donors
- 4
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 1
- Molecule type
- Small molecule
- Indications
- neoplasm
via ChEMBL · EBI
Research
17,084 papers- Nitroarginine inhibits endothelium-derived relaxation.Japanese journal of pharmacology · 1990
- Microalbuminuria in Rats Treated with D-Nitroarginine Methyl Ether.Bulletin of experimental biology and medicine · 2024
- Scintillation proximity assay to measure nitroarginine and tetrahydrobiopterin binding to heme domain of neuronal nitric oxide synthase.Methods in enzymology · 1999
- Equilibria, kinetics and mechanism for the degradation of the cytotoxic compound L-N(G)-nitroarginine.Drug development and industrial pharmacy · 2018
- Mobile proton triggered radical fragmentation of nitroarginine containing peptides.Journal of the American Society for Mass Spectrometry · 2014
via PubMed
Wikidata facts
- Mass
- 219.097
Show 5 more facts
- chemical formula
- C₆H₁₃N₅O₄
- isomeric SMILES
- C(C[C@@H](C(=O)O)N)CN=C(N)N[N+](=O)[O-]
- canonical SMILES
- C(CC(C(=O)O)N)CN=C(N)N[N+](=O)[O-]
- subject has role
- enzyme inhibitor
- found in taxon
- Phoma
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Nitroarginine, or '''Nω-nitro--arginine, also known as L-NOARG''', is a nitro derivative of the amino acid arginine. It is an inhibitor of nitric oxide synthase and hence a vasoconstrictor. As such, it finds widespread use as a biochemical tool in the study of nitric oxide and its biological effects.
Nitroarginine has been used in research studying coronary constriction, and it was found that, in the presence of midazolam vasodilatation was unaffected by nitroarginine. Due to the presence of all three isoforms of nitric oxide synthase in striatal tissue in the forebrain, research has also been conducted on how its inhibition might affect monoamine transport and dopamine half-life in the striatal extracellular space.
Excerpted from Wikipedia’s “nitroarginine” article, available under the CC BY-SA 4.0 licence.