2-amino-4-(carbamimidamidooxy)butanoic acid; sulfuric acid

• ChemBase ID: 163588
• Molecular Formular: C5H14N4O7S
• Molecular Mass: 274.25226
• Monoisotopic Mass: 274.05831981
• SMILES: NC(=N)NOCCC(N)C(=O)O.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.NC(=N)NOCCC(C(=O)O)N
• InChI: InChI=1S/C5H12N4O3.H2O4S/c6-3(4(10)11)1-2-12-9-5(7)8;1-5(2,3)4/h3H,1-2,6H2,(H,10,11)(H4,7,8,9);(H2,1,2,3,4)
• InChIKey: MVIPJKVMOKFIEV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-(carbamimidamidooxy)butanoic acid; sulfuric acid
• IUPAC Traditional name: canavanine; sulfuric acid
• Synonyms: O-[(Aminoiminomethyl)amino]-L-homoserine Sulfate; 2-Amino-4-(guanidinooxy)butyric Acid Sulfate; Canavanine Sulfate; L-Canavanine Sulphate

Database IDs

• CAS Number: 2219-31-0
• PubChem SID: 162257723
• PubChem CID: 24212197

CALCULATED PROPERTIES

• Acid pKa: 2.103241
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -6.407742
• LogD (pH = 7.4): -5.1360126
• Log P: -3.7018805
• Molar Refractivity: 61.2436 cm^3
• Polarizability: 15.848996 Å^3
• Polar Surface Area: 134.45 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C175500

A Nitric Oxide Synthase inhibitor.

REFERENCES

• Knowles, et al.: Biochem. J., 298, 249 (1994)
• Dokita, et al.: Eur. J. Pharm., 269, 269 (1994)