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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-14 13:30:57 UTC
Update Date2022-03-06 23:35:02 UTC
HMDB IDHMDB0288684
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(24:0/18:3(9,11,15)-OH(13))
DescriptionPC(24:0/18:3(9,11,15)-OH(13)) is an oxidized phosphatidylcholine (PC or GPCho). Oxidized phosphatidylcholines are glycerophospholipids in which a phosphorylcholine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylcholines belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396 ). As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PC(24:0/18:3(9,11,15)-OH(13)), in particular, consists of one chain of one tetracosanoyl at the C-1 position and one chain of 13-hydroxyoctadecatrienoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PCs can be synthesized via three different routes. In one route, the oxidized PC is synthetized de novo following the same mechanisms as for PCs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidated acyl chains with an oxidated acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PC backbone, mainely through the action of LOX (PMID: 33329396 ).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC50H94NO9P
Average Molecular Weight884.274
Monoisotopic Molecular Weight883.666620609
IUPAC Name(2-{[(2R)-2-{[(9E,11E,15E)-13-hydroxyoctadeca-9,11,15-trienoyl]oxy}-3-(tetracosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-{[(9E,11E,15E)-13-hydroxyoctadeca-9,11,15-trienoyl]oxy}-3-(tetracosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C\C=C\C(O)C\C=C\CC
InChI Identifier
InChI=1S/C50H94NO9P/c1-6-8-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-27-30-33-37-41-49(53)57-45-48(46-59-61(55,56)58-44-43-51(3,4)5)60-50(54)42-38-34-31-28-25-26-29-32-36-40-47(52)39-35-9-7-2/h9,29,32,35-36,40,47-48,52H,6-8,10-28,30-31,33-34,37-39,41-46H2,1-5H3/b32-29+,35-9+,40-36+/t47?,48-/m1/s1
InChI KeyZQKKKHYPNRPPOU-KSEOIACKSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Not 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
logP6.15ALOGPS
logP10.24ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area131.42 ŲChemAxon
Rotatable Bond Count47ChemAxon
Refractivity266.74 m³·mol⁻¹ChemAxon
Polarizability111.99 ųChemAxon
Number of Rings0ChemAxon
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]+308.41332859911
AllCCS[M+H-H2O]+308.32832859911
AllCCS[M+Na]+308.48432859911
AllCCS[M+NH4]+308.47132859911
AllCCS[M-H]-298.29632859911
AllCCS[M+Na-2H]-302.77132859911
AllCCS[M+HCOO]-307.66632859911
DeepCCS[M+H]+299.70730932474
DeepCCS[M-H]-297.81230932474
DeepCCS[M-2H]-331.04930932474
DeepCCS[M+Na]+306.12930932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(24:0/18:3(9,11,15)-OH(13)) 10V, Negative-QTOFsplash10-014i-0000000009-1c9b52b63c6d2d775cd52021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(24:0/18:3(9,11,15)-OH(13)) 20V, Negative-QTOFsplash10-014i-0011000009-59d444b9199d669227b42021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(24:0/18:3(9,11,15)-OH(13)) 40V, Negative-QTOFsplash10-014l-0099000009-76b94bc9e8365a5fe4952021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(24:0/18:3(9,11,15)-OH(13)) 10V, Positive-QTOFsplash10-001i-0000000090-515c323690dc089d6b932021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(24:0/18:3(9,11,15)-OH(13)) 20V, Positive-QTOFsplash10-001i-0600000090-c7abc6c3e16aae0d759c2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(24:0/18:3(9,11,15)-OH(13)) 40V, Positive-QTOFsplash10-001i-1900031130-30fef7f2ea2527d7ea6b2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(24:0/18:3(9,11,15)-OH(13)) 10V, Positive-QTOFsplash10-0006-0000000090-f101def8ad08cf7b37032021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(24:0/18:3(9,11,15)-OH(13)) 20V, Positive-QTOFsplash10-0006-0000000090-500521f68914d222ac9a2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(24:0/18:3(9,11,15)-OH(13)) 40V, Positive-QTOFsplash10-0bu3-0200292840-8d66d4c57ffd5291c4062021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(24:0/18:3(9,11,15)-OH(13)) 10V, Positive-QTOFsplash10-0a4i-0000000009-b004933e0f2be8835f982021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(24:0/18:3(9,11,15)-OH(13)) 20V, Positive-QTOFsplash10-0a4i-0000000019-87cfeefb60411b1769c82021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(24:0/18:3(9,11,15)-OH(13)) 40V, Positive-QTOFsplash10-006t-0900143911-713c247c7570558376162021-10-21Wishart 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 References
  1. Hajeyah AA, Griffiths WJ, Wang Y, Finch AJ, O'Donnell VB: The Biosynthesis of Enzymatically Oxidized Lipids. Front Endocrinol (Lausanne). 2020 Nov 19;11:591819. doi: 10.3389/fendo.2020.591819. eCollection 2020. [PubMed:33329396 ]

Only showing the first 10 proteins. There are 78 proteins in total.

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
Gene Name:
LYPLA1
Uniprot ID:
O75608
Molecular weight:
24669.355
General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Has transacylase and calcium-independent phospholipase A2 activity. Catalyzes the formation of 1-O-acyl-N-acetylsphingosine and the concomitant release of a lyso-phospholipid (By similarity). May have weak lysophospholipase activity.
Gene Name:
PLA2G15
Uniprot ID:
Q8NCC3
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
General function:
Involved in phospholipase A2 activity
Specific function:
Not known; does not seem to have catalytic activity.
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
General function:
Involved in hydrolase activity
Specific function:
May hydrolyze fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has lysophospholipase activity (By similarity). Deacylates GAP43.
Gene Name:
LYPLA2
Uniprot ID:
O95372
Molecular weight:
24736.71

Transporters

General function:
Involved in ATP binding
Specific function:
Mediates ATP-dependent export of organic anions and drugs from the cytoplasm. Hydrolyzes ATP with low efficiency. Human MDR3 is not capable of conferring drug resistance. Mediates the translocation of phosphatidylcholine across the canalicular membrane of the hepatocyte
Gene Name:
ABCB4
Uniprot ID:
P21439
Molecular weight:
141521.8

Only showing the first 10 proteins. There are 78 proteins in total.