3-amino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide

• ChemBase ID: 159788
• Molecular Formular: C6H7ClN6O
• Molecular Mass: 214.61238
• Monoisotopic Mass: 214.03698655
• SMILES: c1(cnc(c(n1)C(=O)NC(=N)N)N)Cl
• Canonical SMILES: Nc1ncc(nc1C(=O)NC(=N)N)Cl
• InChI: InChI=1S/C6H7ClN6O/c7-2-1-11-4(8)3(12-2)5(14)13-6(9)10/h1H,(H2,8,11)(H4,9,10,13,14)
• InChIKey: PTIMHPOSZRUADS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-amino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide
• IUPAC Traditional name: 3-amino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide
• Synonyms: 5-Deaminoamiloride; N-Amidino-3-amino-6-chloropyrazinecarboxamide; 3-Amino-N-(aminoiminomethyl)-6-chloro-2-pyrazinecarboxamide; 5-H-Amiloride

Database IDs

• CAS Number: 1203-87-8
• PubChem SID: 162253923
• PubChem CID: 159363

CALCULATED PROPERTIES

• Acid pKa: 10.917899
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.5070967
• LogD (pH = 7.4): -0.26524138
• Log P: -0.26096404
• Molar Refractivity: 62.1673 cm^3
• Polarizability: 18.385298 Å^3
• Polar Surface Area: 130.77 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A578690

An inactive Amiloride analogue

REFERENCES

• Besterman, J., et al.: J. Biol. Chem., 264, 2324 (1989)
• Venanzi, C., et al.: J. Med. Chem., 35, 1643 (1989)
• Yamamoto, T., et al.: Chem. Pharm. Bull., 45, 1282 (1989)