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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-13 12:11:43 UTC
Update Date2022-11-30 20:02:13 UTC
HMDB IDHMDB0279409
Secondary Accession NumbersNone
Metabolite Identification
Common NamePIP(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,16E)-OH(18R))
DescriptionPIP(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,16E)-OH(18R)) 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(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,16E)-OH(18R)), in particular, consists of one chain of 9Z,12Z,15Z-octadecatrienoyl at the C-1 position and one chain of 18-hydroxyleicosapentaenoyl 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
{[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-2-{[(5Z,8Z,11Z,14Z,16E,18R)-18-hydroxyicosa-5,8,11,14,16-pentaenoyl]oxy}-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonateGenerator
Chemical FormulaC47H76O17P2
Average Molecular Weight975.056
Monoisotopic Molecular Weight974.455774983
IUPAC Name{[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-2-{[(5Z,8Z,11Z,14Z,16E,18R)-18-hydroxyicosa-5,8,11,14,16-pentaenoyl]oxy}-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonic acid
Traditional Name[(1R,5S)-2,3,4,6-tetrahydroxy-5-{[hydroxy((2R)-2-{[(5Z,8Z,11Z,14Z,16E,18R)-18-hydroxyicosa-5,8,11,14,16-pentaenoyl]oxy}-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy)phosphoryl]oxy}cyclohexyl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(O)(O)=O)C1O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C=C/[C@H](O)CC
InChI Identifier
InChI=1S/C47H76O17P2/c1-3-5-6-7-8-9-10-11-12-16-19-22-25-28-31-34-40(49)60-36-39(37-61-66(58,59)64-47-44(53)42(51)43(52)46(45(47)54)63-65(55,56)57)62-41(50)35-32-29-26-23-20-17-14-13-15-18-21-24-27-30-33-38(48)4-2/h5-6,8-9,11-12,14-15,17-18,23-24,26-27,30,33,38-39,42-48,51-54H,3-4,7,10,13,16,19-22,25,28-29,31-32,34-37H2,1-2H3,(H,58,59)(H2,55,56,57)/b6-5-,9-8-,12-11-,17-14-,18-15-,26-23-,27-24-,33-30+/t38-,39-,42?,43?,44?,45?,46-,47+/m1/s1
InChI KeyYJWIXHQTIBPXNW-GVBBJQOASA-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
logP5.73ALOGPS
logP7.41ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)1.08ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area276.27 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity259.5 m³·mol⁻¹ChemAxon
Polarizability103.36 ųChemAxon
Number of Rings1ChemAxon
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]+309.37432859911
AllCCS[M+H-H2O]+309.75432859911
AllCCS[M+Na]+308.86732859911
AllCCS[M+NH4]+308.98532859911
AllCCS[M-H]-305.3932859911
AllCCS[M+Na-2H]-312.50832859911
AllCCS[M+HCOO]-320.25432859911
DeepCCS[M+H]+286.26730932474
DeepCCS[M-H]-284.53630932474
DeepCCS[M-2H]-318.5730932474
DeepCCS[M+Na]+292.34630932474

Predicted Kovats Retention Indices

Not Available
Spectra
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