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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-13 10:00:32 UTC
Update Date2022-11-30 20:01:45 UTC
HMDB IDHMDB0278447
Secondary Accession NumbersNone
Metabolite Identification
Common NamePIP(16:0/PGJ2)
DescriptionPIP(16:0/PGJ2) is an oxidized phosphatidylinositol phosphate (PIP). As other PIPs, oxidized 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. Phosphatidylinositol phosphates can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PIP(16:0/PGJ2), in particular, consists of one chain of hexadecanoyl at the C-1 position and one chain of Prostaglandin J2 at the C-2 position. 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. Phosphatidylinositol phosphates are usually present at low levels only in tissues, typically at about 1 to 3% of the concentration of phosphatidylinositol.
Structure
Thumb
Synonyms
ValueSource
{[(1S,6R,12Z,15S,19R,20R,21R,22R,23S,24R)-6-[(hexadecanoyloxy)methyl]-3,20,22,23,24-pentahydroxy-19-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,8,18-trioxo-2,4,7-trioxa-3-phosphabicyclo[13.6.3]tetracosa-12,16-dien-21-yl]oxy}phosphonateGenerator
Chemical FormulaC45H78O18P2
Average Molecular Weight969.049
Monoisotopic Molecular Weight968.466339668
IUPAC Name{[(1S,6R,12Z,15S,19R,20R,21R,22R,23S,24R)-6-[(hexadecanoyloxy)methyl]-3,20,22,23,24-pentahydroxy-19-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,8,18-trioxo-2,4,7-trioxa-3lambda5-phosphabicyclo[13.6.3]tetracosa-12,16-dien-21-yl]oxy}phosphonic acid
Traditional Name[(1S,6R,12Z,15S,19R,20R,21R,22R,23S,24R)-6-[(hexadecanoyloxy)methyl]-3,20,22,23,24-pentahydroxy-19-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,8,18-trioxo-2,4,7-trioxa-3lambda5-phosphabicyclo[13.6.3]tetracosa-12,16-dien-21-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@@H]1COP(O)(=O)O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](C\C=C/CCCC(=O)O1)C=CC(=O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@H](O)[C@H]2OP(O)(O)=O
InChI Identifier
InChI=1S/C45H78O18P2/c1-3-5-7-8-9-10-11-12-13-14-15-16-21-25-38(48)59-31-35-32-60-65(57,58)63-45-43(53)42(52)40(50)33(23-20-17-18-22-26-39(49)61-35)27-30-37(47)36(29-28-34(46)24-19-6-4-2)41(51)44(45)62-64(54,55)56/h17,20,27-30,33-36,40-46,50-53H,3-16,18-19,21-26,31-32H2,1-2H3,(H,57,58)(H2,54,55,56)/b20-17-,29-28+,30-27?/t33-,34-,35+,36-,40+,41+,42-,43+,44+,45-/m0/s1
InChI KeyZIASMARBRNHDKM-FAJKXNSUSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effect
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.69ALOGPS
logP6.91ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)0.94ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area293.34 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity243.52 m³·mol⁻¹ChemAxon
Polarizability102 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+301.23232859911
AllCCS[M+H-H2O]+301.61732859911
AllCCS[M+Na]+300.71932859911
AllCCS[M+NH4]+300.83832859911
AllCCS[M-H]-304.51132859911
AllCCS[M+Na-2H]-310.86332859911
AllCCS[M+HCOO]-317.82132859911
DeepCCS[M+H]+304.71130932474
DeepCCS[M-H]-302.98730932474
DeepCCS[M-2H]-338.35530932474
DeepCCS[M+Na]+311.82330932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PIP(16:0/PGJ2) 10V, Negative-QTOFsplash10-014i-0000000009-5418e05aae6f98ac17182021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PIP(16:0/PGJ2) 20V, Negative-QTOFsplash10-014i-3010000209-c873d1596bc577c2a63f2021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PIP(16:0/PGJ2) 40V, Negative-QTOFsplash10-00os-4030009221-058bd5a18511068e81262021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PIP(16:0/PGJ2) 10V, Positive-QTOFsplash10-0gb9-0000000009-9fdb11b216c5a5337e652021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PIP(16:0/PGJ2) 20V, Positive-QTOFsplash10-0udi-1100000059-ec822591042ff3937bef2021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PIP(16:0/PGJ2) 40V, Positive-QTOFsplash10-03di-4600004900-2571c05bf079002e0f9e2021-10-19Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available