Hmdb loader
Record Information
Version5.0
StatusPredicted
Creation Date2021-09-13 06:36:56 UTC
Update Date2022-11-30 20:00:58 UTC
HMDB IDHMDB0276885
Secondary Accession NumbersNone
Metabolite Identification
Common NamePI(18:3(9Z,12Z,15Z)/PGD2)
DescriptionPI(18:3(9Z,12Z,15Z)/PGD2) is an oxidized phosphatidylinositol (PI). Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PI(18:3(9Z,12Z,15Z)/PGD2), in particular, consists of one chain of 9Z,12Z,15Z-octadecatrienoyl at the C-1 position and one chain of Prostaglandin D2 at the C-2 position. The inositol group that is part of every phosphatidylinositol lipid is covalently linked to the phosphate group that acts as a bridge to the lipid tail. In most organisms, the stereochemical form of this inositol is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial), although other forms can be found in certain plant phosphatidylinositols. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be 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 by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol.
Structure
Thumb
Synonyms
ValueSource
[(1R,6R,12Z,15S,16S,19R,20R,21R,22R,23S,24R)-3,16,20,21,22,23,24-Heptahydroxy-19-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,8,18-trioxo-2,4,7-trioxa-3-phosphabicyclo[13.6.3]tetracos-12-en-6-yl]methyl (9Z,12Z)-octadeca-9,12,15-trienoic acidGenerator
Chemical FormulaC47H77O16P
Average Molecular Weight929.091
Monoisotopic Molecular Weight928.494923397
IUPAC Name[(1R,6R,12Z,15S,16S,19R,20R,21R,22R,23S,24R)-3,16,20,21,22,23,24-heptahydroxy-19-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,8,18-trioxo-2,4,7-trioxa-3lambda5-phosphabicyclo[13.6.3]tetracos-12-en-6-yl]methyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
Traditional Name[(1R,6R,12Z,15S,16S,19R,20R,21R,22R,23S,24R)-3,16,20,21,22,23,24-heptahydroxy-19-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3,8,18-trioxo-2,4,7-trioxa-3lambda5-phosphabicyclo[13.6.3]tetracos-12-en-6-yl]methyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
CAS Registry NumberNot Available
SMILES
CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](O)[C@@H](O)[C@H]2OP(O)(=O)OC[C@@H](COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCC\C=C/C[C@@H]([C@@H](O)CC1=O)[C@@H](O)[C@H](O)[C@H]2O
InChI Identifier
InChI=1S/C47H77O16P/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-23-27-40(51)60-32-35-33-61-64(58,59)63-47-45(56)43(54)37(30-29-34(48)25-21-6-4-2)39(50)31-38(49)36(42(53)44(55)46(47)57)26-22-19-20-24-28-41(52)62-35/h5,7,9-10,12-13,19,22,29-30,34-38,42-49,53-57H,3-4,6,8,11,14-18,20-21,23-28,31-33H2,1-2H3,(H,58,59)/b7-5-,10-9-,13-12-,22-19-,30-29+/t34-,35+,36-,37-,38-,42+,43+,44-,45+,46+,47+/m0/s1
InChI KeySIZQIKDHPVRAMP-FUXRRGJZSA-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
logP4.19ALOGPS
logP5.65ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area267.04 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity245.53 m³·mol⁻¹ChemAxon
Polarizability101.74 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]+297.53632859911
AllCCS[M+H-H2O]+297.87232859911
AllCCS[M+Na]+297.0832859911
AllCCS[M+NH4]+297.18732859911
AllCCS[M-H]-292.72132859911
AllCCS[M+Na-2H]-299.63832859911
AllCCS[M+HCOO]-307.20332859911
DeepCCS[M+H]+296.05530932474
DeepCCS[M-H]-294.13130932474
DeepCCS[M-2H]-328.08930932474
DeepCCS[M+Na]+302.2730932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PI(18:3(9Z,12Z,15Z)/PGD2) 10V, Positive-QTOFsplash10-01t9-2000000039-0a51e14be38c3f100a442021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PI(18:3(9Z,12Z,15Z)/PGD2) 20V, Positive-QTOFsplash10-03fv-9100000064-8b2444c02377911a8dee2021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PI(18:3(9Z,12Z,15Z)/PGD2) 40V, Positive-QTOFsplash10-00di-1930012000-56dbaf8a7ad88406380e2021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PI(18:3(9Z,12Z,15Z)/PGD2) 10V, Negative-QTOFsplash10-056r-0000000009-7ae9875d569adbd3fe1a2021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PI(18:3(9Z,12Z,15Z)/PGD2) 20V, Negative-QTOFsplash10-056r-0020001049-f61f09afa08eafdbfcdc2021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PI(18:3(9Z,12Z,15Z)/PGD2) 40V, Negative-QTOFsplash10-0a6r-9180017010-6c5974d4ef637fe143792021-10-19Wishart 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