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Merck
CN

F6892

Farnesyl pyrophosphate ammonium salt

methanol:ammonia solution, ≥95% (TLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C15H37N3O7P2
CAS Number:
13058-04-3
Molecular Weight:
433.42
NACRES:
NA.83
PubChem Substance ID:
24894923
UNSPSC Code:
12352204
MDL number:
MFCD00189688

Key Documents

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Product Name

Farnesyl pyrophosphate ammonium salt, methanol:ammonia solution, ≥95% (TLC)

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+

SMILES string

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

InChI key

VWFJDQUYCIWHTN-YFVJMOTDSA-N

assay

≥95% (TLC)

form

methanol:ammonia solution

packaging

vial of 200 μg

storage temp.

−20°C

Quality Level

100

Gene Information

rat ... Fnta(25318)

Related Categories

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

Biochem/physiol Actions

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.

General description

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

Physical form

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

signalword

Danger

Hazard Classifications

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

target_organs

Eyes,Central nervous system

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

60.8 °F

flash_point_c

16 °C

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCX1846
MKCV8524
MKCV8393
MKCT0819
MKCV1899

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Protein prenylation and synaptic plasticity: implications for Alzheimer?s disease
Hottman DA and Li L
Molecular Neurobiology, 50(1), 177-185 (2014)
Matrix metalloproteinase-1 contribution to sarcoma cell invasion
Garamszegi N, et al.
Journal of Cellular and Molecular Medicine, 16(6), 1331-1341 (2012)
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)
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
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