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850186P

Avanti

08:0 PI(3,4,5)P3

1,2-dioctanoyl-sn-glycero-3-phospho-(1′-myo-inositol-3′,4′,5′-trisphosphate) (ammonium salt), powder

Synonym(s):

PIP3[3′,4′,5′](8:0/8:0); 110667

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About This Item

Empirical Formula (Hill Notation):
C25H62N4O22P4
CAS Number:
852043-38-0
Molecular Weight:
894.67
UNSPSC Code:
51191904
NACRES:
NA.25

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 100 μg (with stopper and crimp cap (850186P-100ug))
pkg of 1 × 500 μg (with stopper and crimp cap (850186P-500ug))

manufacturer/tradename

Avanti Polar Lipids 850186P

lipid type

phospholipids
cardiolipins

shipped in

dry ice

storage temp.

−20°C

Inchi Code

1S/C25H50O22P4.4H3N/c1-3-5-7-9-11-13-18(26)41-15-17(43-19(27)14-12-10-8-6-4-2)16-42-51(39,40)47-22-20(28)23(44-48(30,31)32)25(46-50(36,37)38)24(21(22)29)45-49(33,34)35;;;;/h17,20-25,28-29H,3-16H2,1-2H3,(H,39,40)(H2,30,31,32)(H2,33,34,35)(H2,36,37,38);4*1H3/t17-,20?,21?,22-,23+,24?,25?;;;;/m1..../s1

InChI key

PUTXTEPMJCMBOI-GFEMPGNRSA-N

SMILES string

[H][C@@](COP(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-])=O)(OC(CCCCCCC)=O)COC(CCCCCCC)=O.[NH4+].[NH4+].[NH4+].[NH4+]

General description

Inositol phospholipid species are membrane-bound signaling molecules that have been implicated in almost all aspects of cellular physiology, including cellular growth, metabolism, proliferation, and survival.
Phosphatidylinositol 3,4,5-trisphosphate (PI(3,4,5)P3) is a less abundant lipid.

Application

08:0 PI(3,4,5)P3 may be used as a control compound for assessing phosphoinositide 3-kinase activity.

Biochem/physiol Actions

Phosphatidylinositol 3,4,5-trisphosphate (PI(3,4,5)P3), a lipid second messenger can modulate synaptic activity.

Packaging

2 mL Amber Serum Vial with Stopper and Crimp Cap (850186P-100ug)
2 mL Amber Serum Vial with Stopper and Crimp Cap (850186P-500ug)

Storage Class Code

11 - Combustible Solids

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

MAK307

Malachite Green Phosphate Assay Kit

Thang Manh Khuong et al.
Neuron, 77(6), 1097-1108 (2013-03-26)
PI(3,4,5)P3 is a low-abundance lipid thought to play a role in the regulation of synaptic activity; however, the mechanism remains obscure. We have constructed novel split Venus-based probes and used superresolution imaging to localize PI(3,4,5)P3 at Drosophila larval neuromuscular synapses. We find
Rays H Y Jiang et al.
Cell host & microbe, 11(2), 99-100 (2012-02-22)
Survival of blood stage malaria parasites requires extensive host cell remodeling, which is facilitated by secretion of parasite proteins via a dedicated protein export pathway. In a recent Cell paper, Bhattacharjee et al., (2012) describe PI(3)P binding as one of the
Sulochanadevi Baskaran et al.
Molecular cell, 47(3), 339-348 (2012-06-19)
Macroautophagy is essential to cell survival during starvation and proceeds by the growth of a double-membraned phagophore, which engulfs cytosol and other substrates. The synthesis and recognition of the lipid phosphatidylinositol 3-phosphate, PI(3)P, is essential for autophagy. The key autophagic
Gerald R V Hammond et al.
Science (New York, N.Y.), 337(6095), 727-730 (2012-06-23)
The quantitatively minor phospholipid phosphatidylinositol (4,5)-bisphosphate [PI(4,5)P(2)] fulfills many cellular functions in the plasma membrane (PM), whereas its synthetic precursor, phosphatidylinositol 4-phosphate (PI4P), has no assigned PM roles apart from PI(4,5)P(2) synthesis. We used a combination of pharmacological and chemical

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