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F6892

Sigma-Aldrich

Farnesyl pyrophosphate ammonium salt

methanol:ammonia solution, ≥95% (TLC)

Synonyme(s) :

3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl pyrophosphate ammonium salt, FPP

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About This Item

Formule empirique (notation de Hill):
C15H37N3O7P2
Numéro CAS:
13058-04-3
Poids moléculaire :
433.42
Numéro MDL:
MFCD00189688
Code UNSPSC :
12352204
ID de substance PubChem :
24894923
Nomenclature NACRES :
NA.83

Niveau de qualité

100

Pureté

≥95% (TLC)

Forme

methanol:ammonia solution

Conditionnement

vial of 200 μg

Température de stockage

−20°C

Chaîne SMILES 

C\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O

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+

Clé InChI

VWFJDQUYCIWHTN-YFVJMOTDSA-N

Informations sur le gène

rat ... Fnta(25318)

Description générale

Farnesyl pyrophosphate is a 15-carbon isoprenoid synthesized from geranyl pyrophosphate (GPP) by the action of enzyme farnesyl pyrophosphate synthase (FPPS).

Application

Farnesyl pyrophosphate ammonium salt has been used:
  • as a prenylation agonist in human osteogenic sarcoma cells in collagen-based cell invasion assays
  • in the prenylation of the hepatocyte growth factor (HGF) in human umbilical vein endothelial cells (HUVECs)
  • as a substrate in prenyltransferases assay in diatom Haslea ostrearia

Actions biochimiques/physiologiques

Farnesyl pyrophosphate (FPP) is the precursor for the biosynthesis of cholesterol, ubiquinone and dolicol. It is part of the intracellular mevalonate pathway. FPP is essential for cell survival and is used for prenylation of several low molecular mass G proteins, including Ras. Inhibition of prenylation results in loss of oncogenic potential of Ras proteins. Inhibition of prenylation may serve as therapeutic potential for management of synaptic plasticity and Alzheimer′s disease.

Forme physique

Solution in methanol: 10mM aqueous NH4OH (7:3)
Actual concentration given on label

Pictogrammes

FlameSkull and crossbonesHealth hazard
GHS02,GHS06,GHS08

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 1

Organes cibles

Eyes,Central nervous system

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

60.8 °F

Point d'éclair (°C)

16 °C

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Consulter la Bibliothèque de documents

Protein prenylation and synaptic plasticity: implications for Alzheimer?s disease
Hottman DA and Li L
Molecular Neurobiology, 50(1), 177-185 (2014)
John M Sanders et al.
Journal of medicinal chemistry, 48(8), 2957-2963 (2005-04-15)
We report the design, synthesis and testing of a series of novel bisphosphonates, pyridinium-1-yl-hydroxy-bisphosphonates, based on the results of comparative molecular similarity indices analysis and pharmacophore modeling studies of farnesyl diphosphate synthase (FPPS) inhibition, human Vgamma2Vdelta2 T cell activation and
Structural characterization of substrate and inhibitor binding to farnesyl pyrophosphate synthase from Pseudomonas aeruginosa
Schmidberger JW, et al.
Acta Crystallographica Section D, Biological Crystallography, 71(3), 721-731 (2015)
Protein prenylation: enzymes, therapeutics, and biotechnology applications
Palsuledesai CC and Distefano MD
ACS Chemical Biology, 10(1), 51-62 (2014)
Chantal Brämer et al.
Biotechnology progress, 35(4), e2812-e2812 (2019-04-02)
The natural production of patchouli oil in developing countries cannot meet the increasing demand any more. This leads to socioecological consequences, such as the use of arable land, which is actually intended for food. Hence, the world market price increased
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