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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-13 12:23:59 UTC
Update Date2022-11-30 20:02:15 UTC
HMDB IDHMDB0279496
Secondary Accession NumbersNone
Metabolite Identification
Common NamePIP(20:0/5-iso PGF2VI)
DescriptionPIP(20:0/5-iso PGF2VI) 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(20:0/5-iso PGF2VI), in particular, consists of one chain of eicosanoyl at the C-1 position and one chain of 5-iso Prostaglandin F2alpha-VI 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,10Z,13R,14S,16R,17S,19R,20R,21S,22R)-3,14,16,18,20,21,22-heptahydroxy-17-[(3R)-3-hydroxyoct-1-en-1-yl]-6-[(icosanoyloxy)methyl]-3,8-dioxo-2,4,7-trioxa-3-phosphabicyclo[11.6.3]docos-10-en-19-yl]oxy}phosphonateGenerator
Chemical FormulaC47H86O19P2
Average Molecular Weight1017.134
Monoisotopic Molecular Weight1016.523854545
IUPAC Name{[(1S,6R,10Z,13R,14S,16R,17S,18R,19R,20R,21S,22R)-3,14,16,18,20,21,22-heptahydroxy-17-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-6-[(icosanoyloxy)methyl]-3,8-dioxo-2,4,7-trioxa-3lambda5-phosphabicyclo[11.6.3]docos-10-en-19-yl]oxy}phosphonic acid
Traditional Name[(1S,6R,10Z,13R,14S,16R,17S,18R,19R,20R,21S,22R)-3,14,16,18,20,21,22-heptahydroxy-17-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-6-[(icosanoyloxy)methyl]-3,8-dioxo-2,4,7-trioxa-3lambda5-phosphabicyclo[11.6.3]docos-10-en-19-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCC(=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/CC(=O)O1)[C@@H](O)C[C@@H](O)[C@H](\C=C/[C@H](O)CCCCC)[C@@H](O)[C@H]2OP(O)(O)=O
InChI Identifier
InChI=1S/C47H86O19P2/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-27-40(51)62-32-35-33-63-68(60,61)66-47-45(56)44(55)42(53)36(26-23-24-28-41(52)64-35)38(49)31-39(50)37(30-29-34(48)25-21-6-4-2)43(54)46(47)65-67(57,58)59/h23-24,29-30,34-39,42-50,53-56H,3-22,25-28,31-33H2,1-2H3,(H,60,61)(H2,57,58,59)/b24-23-,30-29-/t34-,35-,36-,37+,38+,39-,42-,43?,44+,45-,46-,47+/m1/s1
InChI KeyWNTJJGCZBSVBTI-AHLWAVODSA-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
logP3.67ALOGPS
logP5.89ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)0.96ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area316.73 ŲChemAxon
Rotatable Bond Count29ChemAxon
Refractivity254.14 m³·mol⁻¹ChemAxon
Polarizability110.51 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]+310.18932859911
AllCCS[M+H-H2O]+310.64132859911
AllCCS[M+Na]+309.60132859911
AllCCS[M+NH4]+309.73732859911
AllCCS[M-H]-316.33232859911
AllCCS[M+Na-2H]-321.9532859911
AllCCS[M+HCOO]-328.10932859911
DeepCCS[M+H]+302.21230932474
DeepCCS[M-H]-300.48930932474
DeepCCS[M-2H]-335.19730932474
DeepCCS[M+Na]+308.77530932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PIP(20:0/5-iso PGF2VI) 10V, Positive-QTOFsplash10-014j-9000000007-98629faebc627dd7e86d2021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PIP(20:0/5-iso PGF2VI) 20V, Positive-QTOFsplash10-00kb-4000000019-bf49aed3f22e6553f9c92021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PIP(20:0/5-iso PGF2VI) 40V, Positive-QTOFsplash10-0abi-7600006900-c1aed0a675718322a6de2021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PIP(20:0/5-iso PGF2VI) 10V, Negative-QTOFsplash10-014i-9000000001-6ae55904e5955518f84b2021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PIP(20:0/5-iso PGF2VI) 20V, Negative-QTOFsplash10-014i-9001000202-06440fe97ba5b5a27e9a2021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PIP(20:0/5-iso PGF2VI) 40V, Negative-QTOFsplash10-004r-3000009202-ce110c636ceb47a8fdcf2021-10-19Wishart 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