Compound: 2149-70-4
SMILES: O=[N+]([O-])NC(=N)NCCC[C@H](N)C(=O)O
InChIKey: MRAUNPAHJZDYCK-BYPYZUCNSA-N
Synonyms: 2149-70-4, NITROARGININE, Nomega-Nitro-L-arginine, N(G)-Nitro-L-arginine, N(G)-Nitroarginine, omega-Nitroarginine, L-NG-nitroarginine, NG-nitroarginine, Ngamma-Nitro-L-arginine, NOLA, 7O8V7H6P2J, NSC-53662, N omega Nitro L Arginine, (2S)-2-amino-5-[[amino(nitramido)methylidene]amino]pentanoic acid, NG Nitroarginine, omega Nitroarginine, NO2Arg, NOARG, NG Nitro L Arginine, N(omega)-Nitroarginine, N omega-Nitro-L-Arginine, omega-Nitro-L-Arginine, N, (2S)-2-amino-5-((amino(nitramido)methylidene)amino)pentanoic acid, RefChem:854315, (2S)-2-amino-5-((N'-nitrocarbamimidoyl)amino)pentanoic acid, (2S)-2-amino-5-(((E)-N'-nitrocarbamimidoyl)amino)pentanoic acid, (2S)-2-amino-5-(((Z)-N'-nitrocarbamimidoyl)amino)pentanoic acid, (2S)-5-((amino(nitramido)methylidene)amino)-2-azaniumylpentanoate, 218-418-9, H-Arg(NO2)-OH, NG-Nitro-L-arginine, L-NNA, N-Nitro-L-arginine, N-OMEGA-NITRO-L-ARGININE, (S)-2-Amino-5-(3-nitroguanidino)pentanoic acid, MFCD00007033, N (g)-NITRO-L-ARGININE, .omega.-Nitroarginine, NSC 53662, N(omega)-Nitro-L-arginine, N.omega.-Nitro-L-arginine, L-Arginine, .omega.-nitro-, N~5~-(N-nitrocarbamimidoyl)-L-ornithine, N5-[Imino(nitroamino)methyl]-L-ornithine, Ornithine, N(5)-(nitroamidino)-, L-, Norvaline, 5-(2-nitroguanidino)-, (+)-, L-Ornithine, N5-(imino(nitroamino)methyl)-, L-Ornithine, N5-[imino(nitroamino)methyl]-, L-ornithine, N~5~-[imino(nitroamino)methyl]-, M03121, NG-NO2-L-Arg, NRG, C6H13N5O4, N|O-Nitro-L-arginine, (2S)-2-amino-5-[[amino(nitramido)methylene]amino]pentanoic acid, nw-nitro-l-arginine, Arginine, N(G)-nitro-, Arginine, .omega.-nitro-, (+)-NG-Nitroarginine, DTXSID2042696, arg(no2), N~5~-[imino(nitroamino)methyl]-L-ornithine, N?-Nitro-L-arginine, hDDAH inhibitor, 2g, NG -nitro-L-arginine, N G-Nitro-L-arginine, Tocris-0664, Arginine, omega-nitro-, H-Arg(NO2), Spectrum2_001478, Spectrum3_001083, Spectrum4_001236, Spectrum5_001019, N(G)-Methyl-L-arginine, L-NOARG; L-NNA, .omega.-Nitro-L-arginine, N(gamma)-nitro-L-arginine, [N(g)-nitro-L-arginine], N(sup G)-Nitro-L-arginine, UNII-7O8V7H6P2J, Lopac0_000818, BSPBio_002726, KBioGR_001732, Arginine, omega-nitro-, L-, DivK1c_001016, DivK1c_001033, SCHEMBL345312, SPECTRUM1502155, SPBio_001435, L-ARGININE, NG-NITRO-, GTPL8759, orb1298139, Arginine, .omega.-nitro-, L-, SCHEMBL26076123, SCHEMBL29357371, CHEBI:27960, HMS503K13, HMS503O07, KBio1_001016, KBio1_001033, KBio3_001946, NINDS_001016, NINDS_001033, Arginine, N(G)-nitro-, (L)-, BDBM235692, HMS1921L10, HMS3262D17, Arginine, N(G)-nitro-, (+)-, ALBB-015801, EINECS 218-418-9, Tox21_500818, AC8432, CCG-39196, EBC-12589, HSCI1_000287, STL466167, ZINC19796052, compound 2 [PMID: 9667974], AKOS005175145, DB04223, LP00818, SDCCGSBI-0050795.P003, IDI1_001016, IDI1_001033, NCGC00024716-01, NCGC00024716-02, NCGC00024716-03, NCGC00024716-04, NCGC00024716-05, NCGC00024716-09, NCGC00261503-01, DS-13295, SY036177, AI3-62168, ORNITHINE, N5-(NITROAMIDINO)-, L-, CS-0003088, EU-0100818, N0660, C03417, EN300-204408, N 5501, SR-01000597670, Q7041453, SR-01000597670-1, BRD-K89223384-001-04-5, BRD-K89223384-001-05-2, (2S)-2-amino-5-(N'-nitrocarbamimidamido)pentanoic acid, Z2768168371
Theoretical properties:
molecular_formula: C6H13N5O4
molecular_weight: 219.20 g/mol
exact_mass: 219.09675391 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 6
heavy_atom_count: 15
topological_polar_surface_area: 160 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: N(gamma)-nitro-L-arginine is an L-arginine derivative that is L-arginine in which the terminal nitrogen of the guanidyl group is replaced by a nitro group. It is a member of guanidines, a N-nitro compound, a non-proteinogenic L-alpha-amino acid and a L-arginine derivative.
chebi: An <small>L</small>-arginine derivative that is <small>L</small>-arginine in which the terminal nitrogen of the guanidyl group is replaced by a nitro group.
chembl: NITROARGININE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 1.0.
wikipedia: Nitroarginine, or Nω-nitro-l-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.