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Merck

LM1906

Avanti

17:0-20:4 PI(3,4,5)P3

Avanti Research™ - A Croda Brand

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C46H96N4O22P4
CAS Number:
1246304-72-2
Molecular Weight:
1181.16
UNSPSC Code:
51191904
NACRES:
NA.25

Key Documents

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Product Name

17:0-20:4 PI(3,4,5)P3, Avanti Research™ - A Croda Brand LM1906, powder

InChI

1S/C46H84O22P4.4H3N/c1-3-5-7-9-11-13-15-17-19-20-21-23-25-27-29-31-33-35-40(48)64-38(36-62-39(47)34-32-30-28-26-24-22-18-16-14-12-10-8-6-4-2)37-63-72(60,61)68-43-41(49)44(65-69(51,52)53)46(67-71(57,58)59)45(42(43)50)66-70(54,55)56;;;;/h11,13,17,19,21,23,2

InChI key

FSWQCDGXUXSIRI-VHLOILQVSA-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](OP(O)([O-])=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+].[NH4+]

form

powder

manufacturer/tradename

Avanti Research™ - A Croda Brand LM1906

packaging

1 ea of 1 × (with stopper and crimp cap (LM1906-1EA))

application(s)

lipidomics
metabolomics

shipped in

dry ice

storage temp.

−20°C

Application

17:0-20:4 PI(3,4,5)P3 or 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1′-myo-inositol-3′,4′,5′-trisphosphate) has been used:
  • as a lipid standard in ultra-performance liquid chromatography-tandem mass spectrometry (UPLC/MS)
  • as an internal standard in lipid extraction from Drosophila larval tissues
  • as an internal standard in liquid chromatography tandem mass spectroscopic (LC-MS/MS) analysis of methylated phosphatidylinositol phosphates (PIPs)

Biochem/physiol Actions

Phosphatidylinositol-3,4,5-triphosphate (PI(3,4,5)P3) is involved in protein activation. It is a critical signaling molecule for several cellular processes and acts as a secondary messenger. PI(3,4,5)P3 is also implicated in human pathogenesis.

General description

Phosphatidylinositol-3,4,5-triphosphate (PI(3,4,5)P3) is localized to the plasma membrane, intracellular sites and the nucleus.

Packaging

2 mL Amber Serum Vial with Stopper and Crimp Cap (LM1906-1EA)

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
Yvonne Lindsay et al.
Journal of cell science, 119(Pt 24), 5160-5168 (2006-12-13)
Phosphatidylinositol (3,4,5) trisphosphate [PtdIns(3,4,5)P3] is a lipid second messenger, produced by Type I phosphoinositide 3-kinases (PI 3-kinases), which mediates intracellular responses to many growth factors. Although PI 3-kinases are implicated in events at both the plasma membrane and intracellular sites
Sanjeev Sharma et al.
Cell reports, 27(7), 1979-1990 (2019-05-16)
Phosphatidylinositol 3,4,5-trisphosphate (PIP3) generation at the plasma membrane is a key event during activation of receptor tyrosine kinases such as the insulin receptor required for normal growth and metabolism. We report that in Drosophila, phosphatidylinositol 5 phosphate 4-kinase (PIP4K) is
Ulrike Bruning et al.
Cell metabolism, 28(6), 866-880 (2018-08-28)
The role of fatty acid synthesis in endothelial cells (ECs) remains incompletely characterized. We report that fatty acid synthase knockdown (FASNKD) in ECs impedes vessel sprouting by reducing proliferation. Endothelial loss of FASN impaired angiogenesis in vivo, while FASN blockade reduced
Taki Nishimura et al.
Molecular cell, 75(5), 1043-1057 (2019-08-14)
The plasma membrane (PM) is composed of a complex lipid mixture that forms heterogeneous membrane environments. Yet, how small-scale lipid organization controls physiological events at the PM remains largely unknown. Here, we show that ORP-related Osh lipid exchange proteins are
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