(2S)-2-amino-5-[(Z)-2-hydroxycarbamimidamido]pentanoic acid; acetic acid

• ChemBase ID: 170699
• Molecular Formular: C8H18N4O5
• Molecular Mass: 250.25232
• Monoisotopic Mass: 250.1277197
• SMILES: C(=N\O)(\NCCC[C@H](N)C(=O)O)/N.CC(=O)O
• Canonical SMILES: CC(=O)O.O/N=C(\NCCC[C@@H](C(=O)O)N)/N
• InChI: InChI=1S/C6H14N4O3.C2H4O2/c7-4(5(11)12)2-1-3-9-6(8)10-13;1-2(3)4/h4,13H,1-3,7H2,(H,11,12)(H3,8,9,10);1H3,(H,3,4)/t4-;/m0./s1
• InChIKey: VYMCYRPQICLHKC-WCCKRBBISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-[(Z)-2-hydroxycarbamimidamido]pentanoic acid; acetic acid
• IUPAC Traditional name: (2S)-2-amino-5-[(Z)-2-hydroxycarbamimidamido]pentanoic acid; acetic acid
• Synonyms: N5-[(Hydroxyamino)iminomethyl]-D-ornithine Acetate; NG-Hydroxy-L-arginine; NOHA; Nω-Hydroxy-L-arginine Monoacetate

Database IDs

• CAS Number: 53598-01-9
• PubChem SID: 164226609
• PubChem CID: 11957565

CALCULATED PROPERTIES

• Acid pKa: 2.1966174
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -5.570274
• LogD (pH = 7.4): -4.0604973
• Log P: -3.853694
• Molar Refractivity: 45.2728 cm^3
• Polarizability: 17.660032 Å^3
• Polar Surface Area: 133.96 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H943750

A possible intermediate in the biosynthesis of nitric oxide from Arginine. Also shown to elicit arterial vasorelaxation.

REFERENCES

• Lyengar, R., et al.: Proc. Natl. Acad. Sci. U.S.A., 84, 6369 (1987)
• Knowles, R.G., et al.: Proc. Natl. Acad. Sci. U.S.A., 86, 5159 (1987)
• Wallace, G.C., et al.: J. Med. Chem., 34, 1748 (1991)