formic acid; {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 169590
• Molecular Formular: C10H14F2N3O9P
• Molecular Mass: 389.2034274
• Monoisotopic Mass: 389.04357211
• SMILES: [C@@H]1(C([C@@H](O[C@@H]1COP(=O)(O)O)n1c(=O)nc(cc1)N)(F)F)O.C(=O)O
• Canonical SMILES: Nc1ccn(c(=O)n1)[C@@H]1O[C@@H]([C@H](C1(F)F)O)COP(=O)(O)O.OC=O
• InChI: InChI=1S/C9H12F2N3O7P.CH2O2/c10-9(11)6(15)4(3-20-22(17,18)19)21-7(9)14-2-1-5(12)13-8(14)16;2-1-3/h1-2,4,6-7,15H,3H2,(H2,12,13,16)(H2,17,18,19);1H,(H,2,3)/t4-,6-,7-;/m1./s1
• InChIKey: IWMDNZSCVDTYEH-OSZBKLCCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: formic acid; {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxyphosphonic acid; formic acid
• Synonyms: 2'-Deoxy-2',2'-difluoro-5'-cytidylic Acid Formate; Gemcitabine Monophosphate Formate Salt

Database IDs

• CAS Number: 116371-67-6
• PubChem SID: 162263722
• PubChem CID: 71317046

CALCULATED PROPERTIES

• Acid pKa: 1.2203383
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -4.0331926
• LogD (pH = 7.4): -5.128387
• Log P: -1.5901057
• Molar Refractivity: 64.1232 cm^3
• Polarizability: 25.219913 Å^3
• Polar Surface Area: 154.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 151-153°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - G305010

Gemcitabine derivative. An antineoplastic agent.

REFERENCES

• Balzarini, J., et al.: Biochem. Pharmacol., 37, 897 (1988)
• Abbruzzese, J., et al.: Investig. New Drugs, 7, 195 (1988)
• Balzarini, J., et al.: J. Biol. Chem., 264, 6127 (1988)
• Chu, C., et al.: Antimicrob. Agents Chemother., 39, 979 (1988)