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Showing Compound PI(18:0/16:0) (FDB026995)

Record Information
Version1.0
Creation date2011-09-21 01:18:22 UTC
Update date2016-06-28 20:13:54 UTC
Primary IDFDB026995
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePI(18:0/16:0)
DescriptionPI(18:0/16:0)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(18:0/16:0), in particular, consists of one octadecanoyl chain to the C-1 atom, and one hexadecanoyl 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
SynonymSource
PIno(18:0/16:0)Lipid Annotator, HMDB
1-stearoyl-2-palmitoyl-sn-glycero-3-phosphoinositolLipid Annotator, HMDB
Phosphatidylinositol(34:0)Lipid Annotator, HMDB
PI(18:0/16:0)Lipid Annotator
1-octadecanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-myo-inositol)Lipid Annotator, HMDB
PIno(34:0)Lipid Annotator, HMDB
Phosphatidylinositol(18:0/16:0)Lipid Annotator, HMDB
1-octadecanoyl-2-hexadecanoyl-sn-glycero-3-phosphoinositolLipid Annotator, HMDB
PI(34:0)Lipid Annotator, HMDB
1-Octadecanoyl-2-hexadecanoyl-sn-glycero-3-O-(1'-myo-inositol)HMDB
1-Stearoyl-2-palmitoyl-sn-glycero-3-oinositolHMDB
Atidylinositol(18:0/16:0)HMDB
Predicted Properties
PropertyValueSource
Water Solubility0.00076 g/LALOGPS
logP7.23ALOGPS
logP9.88ChemAxon
logS-6ALOGPS
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 Count40ChemAxon
Refractivity219.77 m³·mol⁻¹ChemAxon
Polarizability99.27 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC43H83O13P
IUPAC name[(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy]({[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid
InChI IdentifierInChI=1S/C43H83O13P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-36(44)53-33-35(34-54-57(51,52)56-43-41(49)39(47)38(46)40(48)42(43)50)55-37(45)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h35,38-43,46-50H,3-34H2,1-2H3,(H,51,52)/t35-,38?,39-,40?,41?,42?,43-/m1/s1
InChI KeyAWOYEONIQYBDHZ-HGTJTCKHSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](O)C1O)OC(=O)CCCCCCCCCCCCCCC
Average Molecular Weight839.0851
Monoisotopic Molecular Weight838.557129254
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:

Source:

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Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPI(18:0/16:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-e715bbdbc795f73021c72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000000090-e715bbdbc795f73021c72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aow-0075590010-c73668b051c2af2f307a2021-09-22View Spectrum
NMRNot Available
ChemSpider ID24767690
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 IDHMDB09805
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Phosphatidylserine synthase 1PTDSS1P48651
Phosphatidylserine synthase 2PTDSS2Q9BVG9
N-acetylglucosaminyl-phosphatidylinositol de-N-acetylasePIGLQ9Y2B2
Phosphatidylinositol N-acetylglucosaminyltransferase subunit QPIGQQ9BRB3
Phosphatidylinositol N-acetylglucosaminyltransferase subunit APIGAP37287
Phosphatidylinositol N-acetylglucosaminyltransferase subunit HPIGHQ14442
Phosphatidylinositol N-acetylglucosaminyltransferase subunit CPIGCQ92535
GPI mannosyltransferase 1PIGMQ9H3S5
Phosphatidylinositol-glycan biosynthesis class W proteinPIGWQ7Z7B1
Phosphatidylinositol-glycan biosynthesis class X proteinPIGXQ8TBF5
GPI mannosyltransferase 4PIGZQ86VD9
GPI mannosyltransferase 3PIGBQ92521
Phosphatidylinositol-glycan biosynthesis class F proteinPIGFQ07326
GPI ethanolamine phosphate transferase 2PIGGQ5H8A4
GPI ethanolamine phosphate transferase 1PIGNO95427
GPI ethanolamine phosphate transferase 3PIGOQ8TEQ8
GPI transamidase component PIG-SPIGSQ96S52
GPI transamidase component PIG-TPIGTQ969N2
Phosphatidylinositol glycan anchor biosynthesis class U proteinPIGUQ9H490
GPI mannosyltransferase 2PIGVQ9NUD9
Phosphatidylinositol N-acetylglucosaminyltransferase subunit YPIGYQ3MUY2
Phosphatidylserine decarboxylase proenzymePISDQ9UG56
Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2INPPL1O15357
Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 1INPP5DQ92835
Phosphatidylinositol 3,4,5-trisphosphate 3-phosphatase TPTE2TPTE2Q6XPS3
Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit delta isoformPIK3CDO00329
Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta isoformPIK3CBP42338
Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha isoformPIK3CAP42336
Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma isoformPIK3CGP48736
Phospholipase A1 member APLA1AQ53H76
PI-PLC X domain-containing protein 2PLCXD2Q0VAA5
PI-PLC X domain-containing protein 1PLCXD1Q9NUJ7
PI-PLC X domain-containing protein 3PLCXD3Q63HM9
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference