PIP(16:0/18:0) (CHEM039240)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 16:04:19 UTC
Update Date2016-11-09 01:22:02 UTC
Accession NumberCHEM039240
Identification
Common NamePIP(16:0/18:0)
ClassSmall Molecule
DescriptionPIP(16:0/18:0) is a phosphatidylinositol phosphate. Phosphatidylinositol phosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a phosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol phosphates 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 phosphates 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. PIP(16:0/18:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of stearic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the stearic acid moiety is derived from animal fats, coco butter and sesame oil. The most important phosphatidylinositol phosphate in both quantitative and biological terms is phosphatidylinositol 4-phosphate. 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. [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1'-myo-inositol-3'-phosphate)Lipid Annotator, HMDB
1-palmitoyl-2-stearoyl-sn-glycero-3-phosphoinositol-phosphateLipid Annotator, HMDB
PIP(34:0)Lipid Annotator, HMDB
Phosphatidylinositol Phosphate(34:0)Lipid Annotator, HMDB
PIP(16:0/18:0)Lipid Annotator
Phosphatidylinositol Phosphate(16:0/18:0)Lipid Annotator, HMDB
1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphoinositol-phosphateLipid Annotator, HMDB
PIP[3'](16:0/18:0)Lipid Annotator, HMDB
{[(1R,3S)-3-({[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2,4,5,6-tetrahydroxycyclohexyl]oxy}phosphonateGenerator, HMDB
Chemical FormulaC43H84O16P2
Average Molecular Mass919.065 g/mol
Monoisotopic Mass918.523 g/mol
CAS Registry NumberNot Available
IUPAC Name{[(1R,3S)-3-({[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2,4,5,6-tetrahydroxycyclohexyl]oxy}phosphonic acid
Traditional Name[(1R,3S)-3-{[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2,4,5,6-tetrahydroxycyclohexyl]oxyphosphonic acid
SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(O)(O)=O)C1O)OC(=O)CCCCCCCCCCCCCCCCC
InChI IdentifierInChI=1S/C43H84O16P2/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(45)57-35(33-55-36(44)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)34-56-61(53,54)59-43-40(48)38(46)39(47)42(41(43)49)58-60(50,51)52/h35,38-43,46-49H,3-34H2,1-2H3,(H,53,54)(H2,50,51,52)/t35-,38?,39?,40?,41?,42-,43+/m1/s1
InChI KeyWRYRQEZJZJDDMR-CILQWCOCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycerophosphoinositol phosphates. These are lipids containing a common glycerophosphate skeleton linked to at least one fatty acyl chain and an inositol-5-phosphate moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositol phosphates
Direct ParentGlycerophosphoinositol phosphates
Alternative Parents
Substituents
  • Glycerophosphoinositol phosphate
  • 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
  • Secondary alcohol
  • Carboxylic acid ester
  • 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 Solubility0.0073 g/LALOGPS
logP6.03ALOGPS
logP9.76ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)1.08ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area256.04 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity230.64 m³·mol⁻¹ChemAxon
Polarizability103.83 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0004001009-64af0fa0b39a3a77a0a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05q0-5096004001-ea183cbe57fb41a30074Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9045000010-9b5df8694f102e435a67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-4001064049-ac67144921fafddea114Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054o-9011050241-3f34d4bf26183112c388Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00bd-2039401000-271bccb8a60f89fac62fSpectrum
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 IDHMDB0009923
FooDB IDFDB027112
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24767806
ChEBI IDNot Available
PubChem Compound ID131750481
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available