[1-phosphono-2-(pyridin-3-yl)ethyl]phosphonic acid

• ChemBase ID: 166013
• Molecular Formular: C7H11NO6P2
• Molecular Mass: 267.112862
• Monoisotopic Mass: 267.00616034
• SMILES: c1cncc(c1)CC(P(=O)(O)O)P(=O)(O)O
• Canonical SMILES: OP(=O)(C(P(=O)(O)O)Cc1cccnc1)O
• InChI: InChI=1S/C7H11NO6P2/c9-15(10,11)7(16(12,13)14)4-6-2-1-3-8-5-6/h1-3,5,7H,4H2,(H2,9,10,11)(H2,12,13,14)
• InChIKey: KZMOFWIRXNQJET-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [1-phosphono-2-(pyridin-3-yl)ethyl]phosphonic acid
• IUPAC Traditional name: 1-phosphono-2-(pyridin-3-yl)ethylphosphonic acid
• Synonyms: P,P'-[2-(3-Pyridinyl)ethylidene]bisphosphonic Acid; [2-(3-Pyridinyl)ethylidene]bisphosphonic Acid; Deoxy Risedronic Acid

Database IDs

• CAS Number: 75755-10-1
• PubChem SID: 162260146
• PubChem CID: 10468166

CALCULATED PROPERTIES

• Acid pKa: 1.2030034
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -6.1964455
• LogD (pH = 7.4): -6.3997684
• Log P: -3.6415365
• Molar Refractivity: 55.1581 cm^3
• Polarizability: 21.855965 Å^3
• Polar Surface Area: 127.95 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D253800

Deoxy Risedronic Acid is the deoxy analogue of pyridinyl biphosphonate bone resorption inhibitor Risedronic Acid (R521500). Deoxy Risedronic Acid can be conjugated to create fluorescent bisphosphonate probes to visualize osteoclast resorption in vitro.

REFERENCES

• Kashemirov, B. et al.: Bioconj. Chem., 19, 2308 (2008)
• Sietsema, W.K. et al.: Drug Exp. Clin. Res., 15, 389 (2008)
• Szabo, C.M. et al.: J. Med. Chem., 45, 2894 (2008)