[3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphonic acid

• ChemBase ID: 131283
• Molecular Formular: C39H69O8P
• Molecular Mass: 696.934121
• Monoisotopic Mass: 696.4730058
• SMILES: CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)O)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)COP(=O)(O)O
• InChI: InChI=1S/C39H69O8P/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-39(41)47-37(36-46-48(42,43)44)35-45-38(40)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h11,13,17-18,20,22,26,28,37H,3-10,12,14-16,19,21,23-25,27,29-36H2,1-2H3,(H2,42,43,44)/b13-11-,18-17-,22-20-,28-26-
• InChIKey: SPYWWYSOADUXOQ-BMPTZMRASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphonic acid
• IUPAC Traditional name: 3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid
• Synonyms: Ca2+-activated phospholipid-dependent serine-threonine kinase ζ isozyme human; PKCζ human; Protein Kinase Cζ isozyme human

Database IDs

• MDL Number: MFCD03458228
• PubChem SID: 162225561; 24898083
• PubChem CID: 16219812
• Enzyme Commission Number: IUBMB ); 2.7.1.37 ( BRENDA

CALCULATED PROPERTIES

• Acid pKa: 1.317406
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 9.782457
• LogD (pH = 7.4): 8.760826
• Log P: 12.210115
• Molar Refractivity: 201.4422 cm^3
• Polarizability: 77.96821 Å^3
• Polar Surface Area: 119.36 Å^2
• Rotatable Bonds: 36
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: buffered aqueous solution

Safety Information

• German water hazard class: 1
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -70°C

Pharmacology Properties

• Gene Information: human ... PRKCZ(5590)

Product Information

• Purity: ≥75% (SDS-PAGE)
• Shipped in: dry ice
• Recombinant: expressed in baculovirus infected insect cells
• Mol. Weight: mol wt 76-80 kDa by SDS-PAGE

DETAILS

Sigma Aldrich - P0194

Physical form
Solution in 20 mM HEPES, pH 7.5; 2 mM EDTA, 2 mM EGTA, 5 mM DTT, 250 mM NaCl, 0.05% Triton X-100, and 50% glycerol.
Biochem/physiol Actions
Protein Kinase C (PKC) is a serine/threonine kinase that is activated intracellularly by signal transduction pathways that produce DAG from phosphatidylinositol diphosphate (PIP2) and phosphatidylcholine (PC) through the action of various activated phospholipases. Phorbol esters also stimulate PKC. At least 11 PKC isozymes have been identified that differ in primary structure, tissue distribution, subcellular localization, response to extracellular signals, and substrate specificity. The isozymes can be grouped into three subfamilies. Members of the first family require Ca2+ and phospholipid and include PKCα, βI, βII, and γ. Members of the second family are phospholipid-dependent but Ca2+-independent, and include PKCδ, ε, η, and θ. Members of the third family are not activated by either DAG or phorbol esters and include PKCξ, μ, and ι.Phosphorylation appears to be an important mechanism of regulation of all PKCs. PKC plays a role in the regulation of cell transformation, growth, differentiation, ruffling, vesicle trafficking, apoptosis and gene expression.
Suitability
PKC ε can transfer 1100 nmole of phosphate to PKC ε substrate peptide per minute per mg of total protein at 30 °C.