Showing metabocard for PI(16:0/18:2(9Z,12Z)) (BMDB0009784)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:50:15 UTC
Update Date2020-05-11 20:41:59 UTC
BMDB IDBMDB0009784
Secondary Accession Numbers
  • BMDB09784
Metabolite Identification
Common NamePI(16:0/18:2(9Z,12Z))
DescriptionPI(16:0/18:2(9Z,12Z))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(16:0/18:2(9Z,12Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9Z,12Z-octadecadienoyl to the C-2 atom. The inositol group that is part of every phosphatidylinositol lipid is covalently linked to the phosphate group that acts as a bridge to the lipid tail. In most organisms, the stereochemical form of this inositol is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial), although other forms can be found in certain plant phosphatidylinositols. 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-16:0-2-18:2-PhosphatidylinositolChEBI
1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1'-myo-inositol)ChEBI
1-Hexadecanoyl-2-linoleoyl-sn-glycero-3-phospho-D-myo-inositolChEBI
1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphoinositolChEBI
16:0-18:2-PIChEBI
Phosphatidylinositol(16:0/18:2)ChEBI
Phosphatidylinositol(16:0/18:2omega6)ChEBI
Phosphatidylinositol(34:2)ChEBI
PI(16:0/18:2)ChEBI
PI(16:0/18:2omega6)ChEBI
PI(34:2)ChEBI
PIno(16:0/18:2)ChEBI
PIno(16:0/18:2omega6)ChEBI
PIno(34:2)ChEBI
1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-D-myo-inositolHMDB
1-Palmitoyl-2-linoleoyl-gpiHMDB
1-Palmitoyl-2-linoleoyl-glycero-3-phospho-(1'-myo-inositol)HMDB
1-Palmitoyl-2-linoleoyl-glycero-3-phospho-(1’-myo-inositol)HMDB
1-Palmitoyl-2-linoleoyl-sn-glycero-3-phospho-D-myo-inositolHMDB
GPI(16:0/18:2(9Z,12Z))HMDB
GPI(16:0/18:2)HMDB
GPI(16:0/18:2n6)HMDB
GPI(16:0/18:2W6)HMDB
GPI(34:2)HMDB
PI(16:0/18:2n6)HMDB
PI(16:0/18:2W6)HMDB
Phosphatidylinositol(16:0/18:2(9Z,12Z))HMDB
Phosphatidylinositol(16:0/18:2n6)HMDB
Phosphatidylinositol(16:0/18:2W6)HMDB
PI(16:0/18:2(9Z,12Z))ChEBI
Chemical FormulaC43H79O13P
Average Molecular Weight835.066
Monoisotopic Molecular Weight834.525829602
IUPAC Name[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid
Traditional Name(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy([(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C43H79O13P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(45)55-35(34-54-57(51,52)56-43-41(49)39(47)38(46)40(48)42(43)50)33-53-36(44)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13,17-18,35,38-43,46-50H,3-10,12,14-16,19-34H2,1-2H3,(H,51,52)/b13-11-,18-17-/t35-,38-,39-,40+,41-,42-,43-/m1/s1
InChI KeyBSNJSZUDOMPYIR-CUKLWHKZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-phosphatidyl-1d-myo-inositols. These are lipids containing a myo-inositol attached to the phosphate group of a glycerol-3-phosphate moiety, and two acyl chains linked to the glycerol at the O1- and O2- positions, through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositols
Direct Parent1-phosphatidyl-1D-myo-inositols
Alternative Parents
Substituents
  • 1-phosphatidyl-1d-myo-inositol
  • Inositol phosphate
  • Cyclohexanol
  • Fatty acid ester
  • Dialkyl phosphate
  • Cyclitol or derivatives
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
  • 1-hexadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:73212 )
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.11ALOGPS
logP9.16ChemAxon
logS-5.9ALOGPS
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
Refractivity222 m³·mol⁻¹ChemAxon
Polarizability96.62 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000090-06d9513324fc7d303a96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000000090-06d9513324fc7d303a96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-012c-0075590010-8b3e4e9735b0a7e77d24View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Brain
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0009784
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28639235
KEGG Compound IDNot Available
BioCyc IDCPD-8321
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID73212
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available