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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-14 05:49:01 UTC
Update Date2022-03-06 23:33:52 UTC
HMDB IDHMDB0285586
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(14:0/20:3(8Z,11Z,14Z)-O(5,6))
DescriptionPC(14:0/20:3(8Z,11Z,14Z)-O(5,6)) 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(14:0/20:3(8Z,11Z,14Z)-O(5,6)), in particular, consists of one chain of one tetradecanoyl at the C-1 position and one chain of 5,6-epoxyeicosatrienoyl 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 FormulaC42H76NO9P
Average Molecular Weight770.042
Monoisotopic Molecular Weight769.525770029
IUPAC Nametrimethyl(2-{[(2R)-2-[(4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trien-1-yl]oxiran-2-yl}butanoyl)oxy]-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)azanium
Traditional Nametrimethyl(2-{[(2R)-2-[(4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trien-1-yl]oxiran-2-yl}butanoyl)oxy]-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)azanium
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC1OC1C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C42H76NO9P/c1-6-8-10-12-14-16-18-20-21-23-25-27-30-39-40(52-39)31-29-33-42(45)51-38(37-50-53(46,47)49-35-34-43(3,4)5)36-48-41(44)32-28-26-24-22-19-17-15-13-11-9-7-2/h14,16,20-21,25,27,38-40H,6-13,15,17-19,22-24,26,28-37H2,1-5H3/b16-14-,21-20-,27-25-/t38-,39?,40?/m1/s1
InChI KeyJYPNXJQYEXPLII-KUGOMMNESA-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
logP4.94ALOGPS
logP6.62ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area123.72 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity227.94 m³·mol⁻¹ChemAxon
Polarizability91.42 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]+283.93432859911
AllCCS[M+H-H2O]+283.79232859911
AllCCS[M+Na]+284.0632859911
AllCCS[M+NH4]+284.03632859911
AllCCS[M-H]-274.37132859911
AllCCS[M+Na-2H]-279.27532859911
AllCCS[M+HCOO]-284.67432859911
DeepCCS[M+H]+268.53530932474
DeepCCS[M-H]-266.2130932474
DeepCCS[M-2H]-299.18530932474
DeepCCS[M+Na]+274.27630932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(14:0/20:3(8Z,11Z,14Z)-O(5,6)) 10V, Negative-QTOFsplash10-0udi-0000000090-5e053572644ddb6546482021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(14:0/20:3(8Z,11Z,14Z)-O(5,6)) 20V, Negative-QTOFsplash10-0udi-0011000090-30d9b88f43bfe6be70a32021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(14:0/20:3(8Z,11Z,14Z)-O(5,6)) 40V, Negative-QTOFsplash10-0vmi-0099000090-87116e31645da3a35d782021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(14:0/20:3(8Z,11Z,14Z)-O(5,6)) 10V, Positive-QTOFsplash10-00di-0000000900-743c3cf81dae872fd3cd2021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(14:0/20:3(8Z,11Z,14Z)-O(5,6)) 20V, Positive-QTOFsplash10-00e9-0600000900-2bc8d786c124399a5c372021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(14:0/20:3(8Z,11Z,14Z)-O(5,6)) 40V, Positive-QTOFsplash10-001i-1900230300-bd2d6d41ff08bebe80a62021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(14:0/20:3(8Z,11Z,14Z)-O(5,6)) 10V, Positive-QTOFsplash10-004i-0000000900-dd43921f983b55019bba2021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(14:0/20:3(8Z,11Z,14Z)-O(5,6)) 20V, Positive-QTOFsplash10-004i-0000000900-cbeaf6367582788e33982021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(14:0/20:3(8Z,11Z,14Z)-O(5,6)) 40V, Positive-QTOFsplash10-00kg-0101490300-4016b47ba4421829f56e2021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(14:0/20:3(8Z,11Z,14Z)-O(5,6)) 10V, Positive-QTOFsplash10-0006-0000000900-1e3cedd873e41e5876872021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(14:0/20:3(8Z,11Z,14Z)-O(5,6)) 20V, Positive-QTOFsplash10-0006-0000000900-24f41756039025db23042021-10-19Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(14:0/20:3(8Z,11Z,14Z)-O(5,6)) 40V, Positive-QTOFsplash10-0a4j-0900449300-11c4993d42b6135557da2021-10-19Wishart 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 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.