L-α-phosphatidylinositol-4,5-bisphosphate (Brain, Porcine) (ammonium salt) - ≥99% , CAS No.383907-42-4

CAS: 383907-42-4 Cat. No.: L130330 Molecular Weight: 1096.385 PubChem CID: 46891799

GRADE & PURITY ≥99%

Synonyms

triazanium;[(2S,4R)-2,3,5-trihydroxy-6-[hydroxy(oxido)phosphoryl]oxy-4-[[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]oxy-3-octadecanoyloxypropoxy]-oxidophosphoryl]oxycyclohexyl] hydrogen phosphate | Trisammonium (2R)-2-{[(5Z,8Z,11Z,14Z)-icosa-5,8,1

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Phosphatidylinositol 4,5-bisphosphate (PIP2) is synthesized from the precursor phosphatidylinositol 4-phosphate(PI4P). PIP2 is a phosphoinositide with three negative charges

Brain PI(4,5)P2 has been used:
• in the preparation of Folch liposome

• in the preparation of giant unilamellar vesicles and multilamellar lipid sheets

• as a substrate for rubidium flux assay

• in the biochemical reaction assay mixture for various lipid kinases like Phosphatidylinositol-3-kinase gamma (PI3Kγ), Phosphatidylinositol-3-kinase beta (PI3Kβ), Phosphatidylinositol-3-kinase gamma (PI3Kα)

Specifications

Synonyms

triazanium;[(2S, 4R)-2, 3, 5-trihydroxy-6-[hydroxy(oxido)phosphoryl]oxy-4-[[(2R)-2-[(5Z, 8Z, 11Z, 14Z)-icosa-5, 8, 11, 14-tetraenoyl]oxy-3-octadecanoyloxypropoxy]-oxidophosphoryl]oxycyclohexyl] hydrogen phosphate | Trisammonium (2R)-2-{[(5Z, 8Z, 11Z, 14Z)-icosa-5, 8, 1

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Phosphatidylinositol 4, 5-bisphosphate (PIP2) is a signaling phospholipid, present in the plasma membrane. It acts as a precursor for inositide 3 phosphate, diacylglycerol. PIP2 is a gating ligand for most of the ion channels. It functions as an activatory

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OC1C(C(C(C(C1O)OP(=O)(O)[O-])OP(=O)(O)[O-])O)O)OC(=O)CCCC=CCC=CCC=CCC=CCCCCC.[NH4+].[NH4+].[NH4+]
• IUPAC Name: triazanium;[(2S,4R)-2,3,5-trihydroxy-6-[hydroxy(oxido)phosphoryl]oxy-4-[[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]oxy-3-octadecanoyloxypropoxy]-oxidophosphoryl]oxycyclohexyl] hydrogen phosphate
• InChIKey: GAIOWTITBYPFJE-JVILRMJCSA-N
• INCHI: 1S/C47H85O19P3.3H3N/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(49)63-39(37-61-40(48)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2)38-62-69(59,60)66-45-42(50)43(51)46(64-67(53,54)55)47(44(45)52)65-68(56,57)58;;;/h11,13,17,19,22,24,28,30,39,42-47,50-52H,3-10,12,14-16,18,20-21,23,25-27,29,31-38H2,1-2H3,(H,59,60)(H2,53,54,55)(H2,56,57,58);3*1H3/b13-11-,19-17-,24-22-,30-28-;;;/t39-,42?,43+,44?,45-,46?,47?;;;/m1.../s1
• Isomeric SMILES: CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])O[C@@H]1C([C@@H](C(C(C1O)OP(=O)(O)[O-])OP(=O)(O)[O-])O)O)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC.[NH4+].[NH4+].[NH4+]
• PubChem CID: 46891799
• Molecular Weight: 1096.385

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Glycerophospholipids
      • Subclass Glycerophosphoinositol phosphates
        • Level5 Phosphatidylinositol phosphates
          • Level6 Phosphatidylinositol-4,5-bisphosphates

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Glycerophospholipids
• Subclass: Glycerophosphoinositol phosphates
• Intermediate Tree Nodes: Phosphatidylinositol phosphates
• Direct Parent: Phosphatidylinositol-4,5-bisphosphates
• Alternative Parents: Phosphatidylinositols Inositol phosphates Fatty acid esters Dialkyl phosphates Cyclohexanols Dicarboxylic acids and derivatives Carboxylic acid esters Polyols Organic salts Organic oxides Organic nitrogen compounds Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Diacylglycerophosphoinositol-4,5-bisphosphate - Diacylglycerophosphoinositol - Glycerophosphoinositol - Inositol phosphate - Cyclohexanol - Fatty acid ester - Dialkyl phosphate - Cyclitol or derivatives - Dicarboxylic acid or derivatives - Organic phosphoric acid derivative - Phosphoric acid ester - Fatty acyl - Alkyl phosphate - Cyclic alcohol - Secondary alcohol - Carboxylic acid ester - Carboxylic acid derivative - Polyol - Carbonyl group - Organooxygen compound - Alcohol - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic salt - Aliphatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phosphatidylinositol-4,5-bisphosphates. These are phosphatidylinositol bisphosphates in which the two phosphate groups are at C-4 and C-5 of the inositol moiety.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y