(2S)-2-amino-5-(1-nitrocarbamimidamido)pentanoic acid

• ChemBase ID: 3836
• Molecular Formular: C6H13N5O4
• Molecular Mass: 219.19852
• Monoisotopic Mass: 219.09675392
• SMILES: N[C@@H](CCCNC(=N)N[N+](=O)[O-])C(=O)O
• Canonical SMILES: N=C(N[N+](=O)[O-])NCCC[C@@H](C(=O)O)N
• InChI: InChI=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
• InChIKey: MRAUNPAHJZDYCK-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-(1-nitrocarbamimidamido)pentanoic acid; (2S)-2-amino-5-(3-nitrocarbamimidamido)pentanoic acid
• IUPAC Traditional name: nitroarginine; (2S)-2-amino-5-(3-nitrocarbamimidamido)pentanoic acid
• Synonyms: Nω-Nitro-L-arginine; N?-Nitro-L-arginine; Nitro-l-arginine; NNA; NRG; Ngamma-nitro-l-arginine; L-NNA; N(g)-nitro-l-arginine; N(g)-nitroarginine; N-omega-nitro-l-arginine; N-nitro-l-arginine; N5-(Nitroamidino)-L-2,5-diaminopentanoic acid; NG-NO2-L-Arg; NG-nitro-l-arginine; Nomega-nitro-l-arginine; Nitroarginine; N~5~-[imino(nitroamino)methyl]-L-ornithine; N^G-NO2-L-Arg; N^5-(Nitroamidino)-L-2,5-diaminopentanoic acid; N-ω-NITRO-L-ARGININE; N5-(nitroamidino)-L-Ornithine; (+)-NG-Nitroarginine; NG-nitro-L-Arginine, L-NG-Nitroarginine; L-NOARG; NG-Nitroarginine; NOLA; NSC 53662; Nω-Nitro-L-arginine; ω-Nitro-L-arginine; ω-Nitroarginine

Database IDs

• CAS Number: 2149-70-4
• EC Number: 218-418-9
• MDL Number: MFCD00007033
• Beilstein Number: 1728914
• PubChem SID: 160967273; 46508354; 24278010
• PubChem CID: 440005
• Wikipedia Title: Nitroarginine

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8305252
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -4.135254
• LogD (pH = 7.4): -3.3700526
• Log P: -3.369066
• Molar Refractivity: 60.9094 cm^3
• Polarizability: 18.928207 Å^3
• Polar Surface Area: 157.05 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.79
• LOG S: -2.4
• Solubility (Water): 8.74e-01 g/l

PROPERTIES

Physical Property

• Melting Point: 255-260 °C; 257 °C (dec.)(lit.); 257°C (decomposes)
• Optical Rotation: [α]20/D +24±1°, c = 4% in 2 M HCl; [α]23/D +23°, c = 2 in 2 M HCl

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: RM2982100
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846)mouse ... Nos2(18126)rat ... Grin2a(24409), Nos1(24598)

Product Information

• Purity: ≥98% (TLC); ≥99.0% (NT); 99%
• Ignition Residue: ≤0.05%
• Linear Formula: O2NNHC(=NH)NH(CH2)3CH(NH2)CO2H
• Empirical Formula (Hill Notation): C6H13N5O4

DETAILS

MP Biomedicals - 02102503

Crystalline

DrugBank - DB04223

• Drug Groups: experimental
• Description: An 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)

Sigma Aldrich - N5501

Biochem/physiol Actions
Irreversible inhibitor of constitutive nitric oxide synthase (nNOS) and a reversible inhibitor of inducible nitric oxide synthase (iNOS).
包装
1 g in poly tube
5, 25 g in poly bottle

Sigma Aldrich - 72750

Biochem/physiol Actions
Irreversible inhibitor of constitutive nitric oxide synthase (nNOS) and a reversible inhibitor of inducible nitric oxide synthase (iNOS).
Other Notes
Nitric oxide synthase inhibitor1