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LM1904

Avanti

17:0-20:4 PI(4,5)P2

Avanti Research™ - A Croda Brand

Synonym(s):

1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1′-myo-inositol-4′,5′-bisphosphate) (ammonium salt)

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About This Item

Empirical Formula (Hill Notation):
C46H92N3O19P3
CAS Number:
1246304-70-0
Molecular Weight:
1084.15
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

17:0-20:4 PI(4,5)P2, Avanti Research™ - A Croda Brand LM1904, powder

application(s)

lipidomics
metabolomics

shipped in

dry ice

InChI

1S/C46H83O19P3.3H3N/c1-3-5-7-9-11-13-15-17-19-20-21-23-25-27-29-31-33-35-40(48)62-38(36-60-39(47)34-32-30-28-26-24-22-18-16-14-12-10-8-6-4-2)37-61-68(58,59)65-44-41(49)42(50)45(63-66(52,53)54)46(43(44)51)64-67(55,56)57;;;/h11,13,17,19,21,23,27,29,38,41-46

InChI key

OKMXNUJCHZSHOL-TZFFBZLFSA-N

SMILES string

[H][C@@](COP([O-])(O[C@H]1[C@H](O)[C@@H](OP(O)([O-])=O)[C@H](OP([O-])(O)=O)[C@@H](O)[C@H]1O)=O)(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)COC(CCCCCCCCCCCCCCCC)=O.[NH4+].[NH4+].[NH4+]

form

powder

manufacturer/tradename

Avanti Research™ - A Croda Brand LM1904

packaging

1 ea of 1 × (with stopper and crimp cap (LM1904-1EA))

storage temp.

−20°C

Application

17:0-20:4 PI(4,5)P2 or 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1′-myo-inositol-4′,5′-bisphosphate) has been used:
  • as an internal standard in liquid chromatography tandem mass spectroscopy (LC-MS/MS) experiments
  • as a lipid standard in ultra-performance liquid chromatography-tandem mass spectrometry (UPLC/MS)
  • as a standard to measure phosphatidylinositol (4,5)P2 from fibroblasts and brain samples by MS

Biochem/physiol Actions

Phosphatidylinositol 4,5-bisphosphate (PI(4,5)P2) is critical for the phosphoinositide signaling. It acts as a primary messenger and can also as a precursor for many secondary messengers involved. PI(4,5)P2 serves as a substrate for phosphoinositide 3-kinase (PI3K) to form phosphatidylinositol 3,4,5-trisphosphate (PI3,4,5P3).

Packaging

2 mL Amber Serum Vial with Stopper and Crimp Cap (LM1904-1EA)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

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Prasenjit Manna et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 35(4), 1253-1275 (2015-02-28)
Phosphatidylinositol-3,4,5-triphosphate (PtdIns(3,4,5)P₃) is one of the most important phosphoinositides and is capable of activating a wide range of proteins through its interaction with their specific binding domains. Localization and activation of these effector proteins regulate a number of cellular functions
Avishek Ghosh et al.
Bioscience reports, 39(10) (2019-10-28)
Phosphatidylinositol-5-phosphate (PI5P) is a low abundance lipid proposed to have functions in cell migration, DNA damage responses, receptor trafficking and insulin signalling in metazoans. However, studies of PI5P function are limited by the lack of scalable techniques to quantify its
Anthony M Battram et al.
The Journal of biological chemistry, 292(5), 1691-1704 (2016-12-03)
The class I PI3K family of lipid kinases plays an important role in integrin αIIbβ3 function, thereby supporting thrombus growth and consolidation. Here, we identify Ras/Rap1GAP Rasa3 (GAP1IP4BP) as a major phosphatidylinositol 3,4,5-trisphosphate-binding protein in human platelets and a key
Maria Saliakoura et al.
Oncogene, 39(14), 2948-2960 (2020-02-09)
Enhanced prostaglandin production promotes the development and progression of cancer. Prostaglandins are generated from arachidonic acid (AA) by the action of cyclooxygenase (COX) isoenzymes. However, how cancer cells are able to maintain an elevated supply of AA for prostaglandin production
Oscar Vivas et al.
Cell reports, 27(9), 2636-2648 (2019-05-30)
There is increasing evidence that the lysosome is involved in the pathogenesis of a variety of neurodegenerative disorders. Thus, mechanisms that link lysosome dysfunction to the disruption of neuronal homeostasis offer opportunities to understand the molecular underpinnings of neurodegeneration and
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