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Showing Compound PIP3(18:0/18:1(11Z)) (FDB027335)

Record Information
Version1.0
Creation date2011-09-21 01:22:55 UTC
Update date2015-07-21 06:59:05 UTC
Primary IDFDB027335
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePIP3(18:0/18:1(11Z))
DescriptionPIP3(18:0/18:1(11Z)) is a phosphatidylinositol trisphosphate. Phosphatidylinositol trisphosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a trisphosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol trisphosphates 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 trisphosphates 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. PIP3(18:0/18:1(11Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the vaccenic acid moiety is derived from butter fat and animal fat. The most important phosphatidylinositol trisphosphate in both quantitative and biological terms is phosphatidylinositol 3,4,5-triphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signalling 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. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP4.71ALOGPS
logP10.04ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)0.38ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-7ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area349.1 ŲChemAxon
Rotatable Bond Count47ChemAxon
Refractivity262.71 m³·mol⁻¹ChemAxon
Polarizability117.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC45H88O22P4
IUPAC name{[(3s,5S)-2,4-dihydroxy-3-({hydroxy[(2R)-2-(octadec-11-enoyloxy)-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)-5,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
InChI IdentifierInChI=1S/C45H88O22P4/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(46)61-35-37(63-39(47)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)36-62-71(59,60)67-42-40(48)43(64-68(50,51)52)45(66-70(56,57)58)44(41(42)49)65-69(53,54)55/h14,16,37,40-45,48-49H,3-13,15,17-36H2,1-2H3,(H,59,60)(H2,50,51,52)(H2,53,54,55)(H2,56,57,58)/t37-,40?,41?,42-,43+,44?,45?/m1/s1
InChI KeyHWWWNKQSEYZFCK-IZURPXOXSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)O[C@@]1([H])C(O)C(OP(O)(O)=O)C(OP(O)(O)=O)[C@@]([H])(OP(O)(O)=O)C1O)OC(=O)CCCCCCCCCC=CCCCCCC
Average Molecular Weight1105.0621
Monoisotopic Molecular Weight1104.471770548
Classification
Description Belongs to the class of organic compounds known as phosphatidylinositol-3,4,5-trisphosphates. These are phosphatidylinositol bisphosphates in which the inositol moiety is substituted by a phosphate group at the C-3, C-4, and C-5 positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositol phosphates
Direct ParentPhosphatidylinositol-3,4,5-trisphosphates
Alternative Parents
Substituents
  • Diacylglycerophosphoinositol-3,4,5-trisphosphate
  • Diacylglycerophosphoinositol
  • Glycerophosphoinositol
  • Inositol phosphate
  • Dialkyl phosphate
  • Monoalkyl 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
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
SpectraNot Available
ChemSpider ID24768029
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 IDHMDB10152
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
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference