PIP2(18:0/16:0) (CHEM039370)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 16:40:50 UTC
Update Date2016-11-09 01:22:04 UTC
Accession NumberCHEM039370
Identification
Common NamePIP2(18:0/16:0)
ClassSmall Molecule
DescriptionPIP2(18:0/16:0) is a phosphatidylinositol bisphosphate. Phosphatidylinositol bisphosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a bisphosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol bisphosphates are generated from phosphatidylinositols which are phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated. Phosphatidylinositols bisphosphates can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PIP2(18:0/16:0), in particular, consists of one chain of stearic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. The most important phosphatidylinositol bisphosphate in both quantitative and biological terms is phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. Phosphatidylinositols phosphates are usually present at low levels only in tissues, typically at about 1 to 3% of the concentration of phosphatidylinositol.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Octadecanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-myo-inositol-3',4'-bisphosphate)HMDB
1-Phosphatidyl-D-myo-inositol 4,5-bisphosphateHMDB
1-Stearoyl-2-palmitoyl-sn-glycero-3-phosphoinositol-bisphosphateHMDB
Phosphatidylinositol diphosphate(18:0/16:0)HMDB
Phosphatidylinositol diphosphate(34:0)HMDB
PIP2(34:0)HMDB
PIP2[3',4'](18:0/16:0)HMDB
{[(1S,3S)-3-({[(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2,4,5-trihydroxy-6-(phosphonooxy)cyclohexyl]oxy}phosphonateHMDB
Chemical FormulaC43H85O19P3
Average Molecular Mass999.045 g/mol
Monoisotopic Mass998.490 g/mol
CAS Registry NumberNot Available
IUPAC Name{[(4S,6S)-4-({[(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2,3,5-trihydroxy-6-(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Name[(4S,6S)-4-{[(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2,3,5-trihydroxy-6-(phosphonooxy)cyclohexyl]oxyphosphonic acid
SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)O[C@H]1C(O)C(O)C(OP(O)(O)=O)[C@@H](OP(O)(O)=O)C1O)OC(=O)CCCCCCCCCCCCCCC
InChI IdentifierInChI=1S/C43H85O19P3/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-36(44)57-33-35(59-37(45)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2)34-58-65(55,56)62-41-38(46)39(47)42(60-63(49,50)51)43(40(41)48)61-64(52,53)54/h35,38-43,46-48H,3-34H2,1-2H3,(H,55,56)(H2,49,50,51)(H2,52,53,54)/t35-,38?,39?,40?,41+,42?,43+/m1/s1
InChI KeyCIKAEWLGOIVQBP-NXVRDOABSA-N
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
  • Cyclohexanol
  • Fatty acid ester
  • Dialkyl phosphate
  • Monoalkyl phosphate
  • Cyclitol or derivatives
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Cyclic alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.054 g/LALOGPS
logP5.01ALOGPS
logP9.64ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)0.63ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area302.57 ŲChemAxon
Rotatable Bond Count44ChemAxon
Refractivity241.52 m³·mol⁻¹ChemAxon
Polarizability108.49 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-4000143029-bb036d8749a87aaeef81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aba-9000170053-f44b0131efc9f42506c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-4289801000-3aeb1987c04f42ff4065Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-0000600109-7537d906e815b7b3486cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004u-9082700701-9ae98651081b16ba75a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9130200000-19189b19cfd1c0b56d23Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0010059
FooDB IDFDB027242
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDPhosphatidylinositols
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24767936
ChEBI IDNot Available
PubChem Compound ID53480250
Kegg Compound IDC00626
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available