Farnesyl pyrophosphate

Names

[ Name ]:
Farnesyl pyrophosphate

[Synonym ]:
MFCD00189688
FARNESYLPYROPHOSPHATE
(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl trihydrogen diphosphate triammoniate
Farnesyl pyrophosphate ammonium salt
Diphosphoric acid, (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl ester, triammonium salt
3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl pyrophosphate ammonium salt FPP

Biological Activity

[Description]:

Farnesyl pyrophosphate, a 15-carbon isoprenoid, is a metabolic intermediate of the mevalonate (MVA) pathway. Farnesyl pyrophosphate is a TRPM2 (TRP Channel) agonist, activates TRPM2 opening for ion influx. Farnesyl pyrophosphate is a key branch substrate for cholesterol synthesis, ubiquinones synthesis, protein farnesylation decoration, and geranyl-geranyl pyrophosphate (GGPP) synthesis[1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel

Research Areas >> Neurological Disease

[In Vitro]

Farnesyl pyrophosphate 作为一种确定的危险信号，可触发急性细胞死亡，导致中风中的神经元丢失。Farnesyl pyrophosphate 含有疏水性 15 碳异戊二烯基链和带大量电荷的焦磷酸头部，导致急性细胞死亡，与其下游代谢途径无关。从机制上讲，细胞外钙流入和阳离子通道瞬时受体电位 melastatin 2 (TRPM2) 在 Farnesyl pyrophosphate 诱导的细胞死亡中发挥重要作用。Farnesyl pyrophosphate 酸激活 TRPM2 开放离子流入[1]。

[In Vivo]

就大脑中动脉闭塞（MCAO）构建的小鼠模型而言，Farnesyl pyrophosphate 在脑内蓄积，表明 Farnesyl pyrophosphate 和TRPM2危险信号轴在缺血性损伤中的作用。Farnesyl pyrophosphate/TRPM2 信号轴和 MVA 通路在脑缺血和潜在的神经退行性疾病中发挥重要作用[1]。

[References]

[1]. Jing Chen, et al. Farnesyl pyrophosphate is a new danger signal inducing acute cell death. PLoS Biol. 2021 Apr 26;19(4):e3001134.

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₅H₃₇N₃O₇P₂

[ Molecular Weight ]:
433.418

[ Flash Point ]:
16 °C - closed cup (lit.)

[ Exact Mass ]:
433.210663

[ PSA ]:
142.63000

[ LogP ]:
5.60360

[ Storage condition ]:
20°C

Safety Information

[ Symbol ]:

GHS02, GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H301 + H311 + H331-H315-H319-H370

[ Precautionary Statements ]:
P210-P260-P280-P301 + P310 + P330-P302 + P352 + P312-P370 + P378

[ Hazard Codes ]:
F;T

[ Risk Phrases ]:
11-23/24/25-39/23/24/25

[ Safety Phrases ]:
7-16-36/37-45

[ RIDADR ]:
UN 1230 3/PG 2

[ HS Code ]:
2905290000

Customs

[ HS Code ]: 2905290000

[ Summary ]:
2905290000 unsaturated monohydric alcohols。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Articles

Lovastatin and perillyl alcohol inhibit glioma cell invasion, migration, and proliferation--impact of Ras-/Rho-prenylation.

Pharmacol. Res. 91 , 69-77, (2015)

Alterations in small GTPase mediated signal transduction pathways have emerged as a central step in the molecular pathogenesis of glioblastoma (GBM), the most common malignant brain tumor in adults. F...

A genetic and pharmacological analysis of isoprenoid pathway by LC-MS/MS in fission yeast.

PLoS ONE 7(11) , e49004, (2012)

Currently, statins are the only drugs acting on the mammalian isoprenoid pathway. The mammalian genes in this pathway are not easily amenable to genetic manipulation. Thus, it is difficult to study th...

In vitro and in vivo anticancer effects of mevalonate pathway modulation on human cancer cells.

Br. J. Cancer 111(8) , 1562-71, (2014)

The increasing usage of statins (the 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors) has revealed a number of unexpected beneficial effects, including a reduction in cancer risk.We investi...