{[hydroxy({[(2E,6E)-3-(2H3)methyl-7,11-dimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid

• ChemBase ID: 168869
• Molecular Formular: C15H28O7P2
• Molecular Mass: 382.326142
• Monoisotopic Mass: 382.1310265
• SMILES: C(=C\COP(=O)(OP(=O)(O)O)O)(/CC/C=C(/CCC=C(C)C)\C)\C
• Canonical SMILES: C/C(=C\COP(=O)(OP(=O)(O)O)O)/CC/C=C(/CCC=C(C)C)\C
• InChI: InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+
• InChIKey: VWFJDQUYCIWHTN-YFVJMOTDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[hydroxy({[(2E,6E)-3-(^2H₃)methyl-7,11-dimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid
• IUPAC Traditional name: {hydroxy[(2E,6E)-3-(^2H₃)methyl-7,11-dimethyldodeca-2,6,10-trien-1-yl]oxyphosphoryl}oxyphosphonic acid
• Synonyms: Diphosphoric Acid P-[(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl-d3] Ester Ammonium Salt; (E,E)-Diphosphoric Acid Mono(3,7,11-trimethyl-2,6,10-dodecatrienyl-d3) Ester Triammonium Salt; Farnesyl Pyrophosphate-d3 Triammonium Salt

Database IDs

• PubChem SID: 162263001
• PubChem CID: 71316712

CALCULATED PROPERTIES

• Acid pKa: 1.7672187
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.78978175
• LogD (pH = 7.4): -1.4174509
• Log P: 3.616733
• Molar Refractivity: 96.7305 cm^3
• Polarizability: 37.048374 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F102472

Labelled Farnesyl Pyrophosphate. Isoprenoid from the intracellular mevalonate pathway used for prenylation of several low molecular mass G proteins, including Ras.

REFERENCES

• Correll, C., et al.: J. Biol. Chem., 269, 17390 (1994)
• Moura, I., et al.: Antimicrob. Agents Chemother., 45, 2553 (1994)
• Gana-Weisz, M., et al.: Clin. Cancer Res., 8, 555 (1994)