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

• ChemBase ID: 154867
• Molecular Formular: C15H31NO7P2
• Molecular Mass: 399.356662
• Monoisotopic Mass: 399.1575756
• SMILES: CC(=CCC/C(=C/CC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)/C)C.N
• Canonical SMILES: C/C(=C\COP(=O)(OP(=O)(O)O)O)/CC/C=C(/CCC=C(C)C)\C.N
• InChI: InChI=1S/C15H28O7P2.H3N/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);1H3/b14-9+,15-11+
• InChIKey: CPYJTMLHKIWGDF-NDHHSALASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid amine
• IUPAC Traditional name: amine farnesyl diphosphate
• Synonyms: (E,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl pyrophosphate ammonium salt; Farnesyl diphosphate ammonium salt; trans,trans-Farnesyl pyrophosphate ammonium salt

Database IDs

• Beilstein Number: 2482197
• PubChem SID: 162249005
• PubChem CID: 16219347

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

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95.0% (HPLC)
• Empirical Formula (Hill Notation): C15H28O7P2 · xNH3

DETAILS

Sigma Aldrich - 44270

Biochem/physiol Actions
Farnesyl pyrophosphate is a key intermediate in the biosynthesis of more complex sesquiterpenoids, higher terpenoids, and steroids1 and different biological functions have been discovered for FPP and the corresponding alcohol farnesol2,3,4,5,6,7. FPP plays an important role in the posttranslational processing of Ras proteins. Mutated forms of Ras are associated with human cancer and are therefore investigated in cancer research5,6.