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Showing Compound PI(16:0/16:0) (FDB026968)

Record Information
Version1.0
Creation date2011-09-21 01:17:58 UTC
Update date2016-06-28 20:13:52 UTC
Primary IDFDB026968
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePI(16:0/16:0)
DescriptionPI(16:0/16:0)is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols 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.PI(16:0/16:0), in particular, consists of two hexadecanoyl chains at positions C-1 and C-2 to the C-2 atom. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol can be 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 by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and 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. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.0014 g/LALOGPS
logP6.79ALOGPS
logP8.99ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area209.51 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity210.57 m³·mol⁻¹ChemAxon
Polarizability95.19 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC41H79O13P
IUPAC name[(2R)-2,3-bis(hexadecanoyloxy)propoxy]({[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid
InChI IdentifierInChI=1S/C41H79O13P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(42)51-31-33(32-52-55(49,50)54-41-39(47)37(45)36(44)38(46)40(41)48)53-35(43)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33,36-41,44-48H,3-32H2,1-2H3,(H,49,50)/t33-,36?,37-,38?,39?,40?,41-/m1/s1
InChI KeyIBUKXRINTKQBRQ-NBURIUCMSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](O)C1O)OC(=O)CCCCCCCCCCCCCCC
Average Molecular Weight811.0319
Monoisotopic Molecular Weight810.525829126
Classification
Description Belongs to the class of organic compounds known as phosphatidylinositols. These are glycerophosphoinositols where the glycerol is esterified with two fatty acids.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositols
Direct ParentPhosphatidylinositols
Alternative Parents
Substituents
  • Diacylglycerophosphoinositol
  • Inositol phosphate
  • Cyclohexanol
  • Dialkyl phosphate
  • Fatty acid ester
  • Cyclitol or derivatives
  • Fatty acyl
  • Alkyl phosphate
  • Dicarboxylic acid or derivatives
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Cyclic alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

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Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPI(16:0/16:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPI(16:0/16:0), TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPI(16:0/16:0), TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPI(16:0/16:0), TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPI(16:0/16:0), TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPI(16:0/16:0), TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPI(16:0/16:0), TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ai0-0061090000-711cd894168f280349692016-09-19View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-eda839378c6d1ca1a21e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000000090-eda839378c6d1ca1a21e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-0075090010-214665ce7a0b6909c1b22021-09-22View Spectrum
NMRNot Available
ChemSpider ID24767663
ChEMBL IDNot Available
KEGG Compound IDC00626
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB09778
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLecithin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference