(2R)-2-{[(tert-butoxy)carbonyl]amino}-5-(3-nitrocarbamimidamido)pentanoic acid

• ChemBase ID: 38714
• Molecular Formular: C11H21N5O6
• Molecular Mass: 319.31434
• Monoisotopic Mass: 319.14918342
• SMILES: N(C(=N)NCCC[C@H](C(=O)O)NC(=O)OC(C)(C)C)[N+](=O)[O-]
• Canonical SMILES: N=C(N[N+](=O)[O-])NCCC[C@H](C(=O)O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C11H21N5O6/c1-11(2,3)22-10(19)14-7(8(17)18)5-4-6-13-9(12)15-16(20)21/h7H,4-6H2,1-3H3,(H,14,19)(H,17,18)(H3,12,13,15)/t7-/m1/s1
• InChIKey: OZSSOVRIEPAIMP-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[(tert-butoxy)carbonyl]amino}-5-(3-nitrocarbamimidamido)pentanoic acid
• IUPAC Traditional name: (2R)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitrocarbamimidamido)pentanoic acid
• Synonyms: N2-[(1,1-Dimethylethoxy)carbonyl]-N5-[imino(nitroamino)methyl]-D-ornithine; Na-Boc-Nw-nitro-D-arginine; Boc-D-Arg(NO2)-OH; Nα-Boc-Nω-nitro-D-arginine; Boc-Nw-nitro-D-arginine

Database IDs

• CAS Number: 50913-12-7
• MDL Number: MFCD00038091
• PubChem SID: 161002021
• PubChem CID: 7021876

CALCULATED PROPERTIES

• Acid pKa: 3.660495
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.2733893
• LogD (pH = 7.4): -2.5259495
• Log P: -1.1886077
• Molar Refractivity: 85.7824 cm^3
• Polarizability: 28.554045 Å^3
• Polar Surface Area: 169.36 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

DETAILS

Toronto Research Chemicals - B658020

Nα-Boc-Nω-nitro-D-arginine is used in the synthesis of selective inactivators of human plasma kallikrein via chloromethyl ketone formation. Nα-Boc-Nω-nitro-D-arginine also produced modest inhibition of the effects acetylcholine in rabbit aorta.

REFERENCES

• Kettner, C. et al.: Biochemistry, 17, 4778 (1978)
• Moore, P.K. et al.: Br. J. Pharmacol., 99, 408 (1978)