Phosphatidylinositol 4,5-bisphosphate (YMDB00133)

Identification
YMDB IDYMDB00133
NamePhosphatidylinositol 4,5-bisphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPhosphatidylinositol 4,5-bisphosphate 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. Phosphatidylinositol 4,5-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Phosphatidylinositol 4,5-bisphosphoric acid
CAS number245126-95-8
WeightAverage: 1042.048
Monoisotopic: 1041.450664914
InChI KeyCNWINRVXAYPOMW-WJUYXORRSA-I
InChIInChI=1S/C47H85O19P3/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)/p-5/b13-11-,19-17-,24-22-,30-28-/t39?,42-,43+,44+,45-,46-,47-/m1/s1
IUPAC NameNot Available
Traditional IUPAC NameNot Available
Chemical FormulaC47H80O19P3
SMILES[H]O[C@]1([H])[C@]([H])(O[H])[C@@]([H])(OP([O-])([O-])=O)[C@]([H])(OP([O-])([O-])=O)[C@@]([H])(O[H])[C@]1([H])OP([O-])(=O)OC([H])([H])C([H])(OC(=O)C([H])([H])C([H])([H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositol phosphates
Direct ParentPhosphatidylinositol-4,5-bisphosphates
Alternative Parents
Substituents
  • Diacylglycerophosphoinositol-4,5-bisphosphate
  • Diacylglycerophosphoinositol
  • Glycerophosphoinositol
  • Inositol phosphate
  • Dialkyl phosphate
  • Fatty acid ester
  • Cyclohexanol
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Charge-5
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.029 g/LALOGPS
logP6.52ALOGPS
logP9.97ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)0.63ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area316.72 ŲChemAxon
Rotatable Bond Count44ChemAxon
Refractivity258.78 m³·mol⁻¹ChemAxon
Polarizability111.22 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Endoplasmic Reticulum, Plasma Membrane
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-9070000000-66701d72c4272a04ceedJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1090000000-b53ecfeb9e76f6796330JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-7190100000-9f2dbeb21f2249f0284dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9010000000-6aa1ee1dcc853b90b72bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9020000000-c68b1d6052f93ede331dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014s-6192000202-a03857e76f8d7446cb6eJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Talwalkar, R. T., Lester, R. L. (1973). "The response of diphosphoinositide and triphosphoinostitide to perturbations of the adenylate energy charge in cells of Saccharomyces cerevisiae." Biochim Biophys Acta 306:412-421.4353706
  • Uno, I., Fukami, K., Kato, H., Takenawa, T., Ishikawa, T. (1988). "Essential role for phosphatidylinositol 4,5-bisphosphate in yeast cell proliferation." Nature 333:188-190.2835684
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID24742074
Kegg IDNot Available
ChemSpider ID25057264
FOODB IDNot Available
WikipediaPhosphatidylinositol_4,5-bisphosphate
BioCyc IDNot Available

Enzymes

Protein Details
1. Probable phosphatidylinositol-3,4,5-trisphosphate 3-phosphatase TEP1
General function:
Involved in protein tyrosine/serine/threonine phosphatase activity
Specific function:
May act as a phosphoinositide 3-phosphatase by regulating PtdIns(3,4,5)P3 levels
Gene Name:
TEP1
Uniprot ID:
P53916
Molecular weight:
50151.5
Reactions
Phosphatidylinositol 3,4,5-trisphosphate + H(2)O → phosphatidylinositol 4,5-bisphosphate + phosphate.