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

• ChemBase ID: 155166
• Molecular Formular: C15H28O7P2
• Molecular Mass: 382.326142
• Monoisotopic Mass: 382.1310265
• SMILES: CC(=CCC/C(=C/CC/C(=C/COP(=O)(O)OP(=O)(O)O)/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)
• InChIKey: VWFJDQUYCIWHTN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({hydroxy[(3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy]phosphoryl}oxy)phosphonic acid; {[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid
• IUPAC Traditional name: farnesyl diphosphate
• Synonyms: 3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl pyrophosphate ammonium salt; FPP; Farnesyl pyrophosphate ammonium salt; Diphosphoric Acid P-[(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl] Ester Ammonium Salt; (E,E)-Diphosphoric Acid Mono(3,7,11-trimethyl-2,6,10-dodecatrienyl) Ester Triammonium Salt; Farnesyl Pyrophosphate Triammonium Salt

Database IDs

• CAS Number: 13058-04-3; 116057-57-9
• MDL Number: MFCD00189688
• PubChem SID: 162249304; 24894923
• PubChem CID: 445713

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

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: methanol:ammonia solution; Pale Yellow Low Melting Solid
• Flash Point: 16 °C; 60.8 °F

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 1230
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301 + H311 + H331-H315-H319-H370
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P305 + P351 + P338-P311
• RID/ADR: UN 1230 3/PG 2
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: rat ... Fnta(25318)

Product Information

• Purity: ≥95% (TLC)
• Packaging: vial of 200 μg
• Empirical Formula (Hill Notation): C15H37N3O7P2

DETAILS

Sigma Aldrich - F6892

Biochem/physiol Actions
Isoprenoid from the intracellular mevalonate pathway used for prenylation of several low molecular mass G proteins, including Ras.
Packaging
1 vial in poly bottle
5 vials in poly bottle
Physical form
Solution in methanol: 10mM aqueous NH4OH (7:3)Actual concentration given on label

Toronto Research Chemicals - F102470

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)