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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-12 03:39:51 UTC
Update Date2022-11-30 19:54:13 UTC
HMDB IDHMDB0261612
Secondary Accession NumbersNone
Metabolite Identification
Common NamePE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6))
DescriptionPE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)) is an oxidized phosphatidylethanolamine (PE). Oxidized phosphatidylethanolamines are glycerophospholipids in which a phosphorylethanolamine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylethanolamines 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, phosphatidylethanolamines 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. PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)), in particular, consists of one chain of one 9Z,12Z,15Z-octadecatrienoyl 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 PEs can be synthesized via three different routes. In one route, the oxidized PE is synthetized de novo following the same mechanisms as for PEs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PE backbone, mainly through the action of LOX (PMID: 33329396 ).
Structure
Thumb
Synonyms
ValueSource
(2-Aminoethoxy)[(2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-[(4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trien-1-yl]oxiran-2-yl}butanoyl)oxy]propoxy]phosphinateGenerator
Chemical FormulaC43H72NO9P
Average Molecular Weight778.021
Monoisotopic Molecular Weight777.4944699
IUPAC Name(2-aminoethoxy)[(2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-[(4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trien-1-yl]oxiran-2-yl}butanoyl)oxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy((2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-[(4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trien-1-yl]oxiran-2-yl}butanoyl)oxy]propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OCCN)OC(=O)CCCC1OC1C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C43H72NO9P/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-33-42(45)49-37-39(38-51-54(47,48)50-36-35-44)52-43(46)34-30-32-41-40(53-41)31-28-26-24-22-20-16-14-12-10-8-6-4-2/h5,7,11-14,17-18,20,22,26,28,39-41H,3-4,6,8-10,15-16,19,21,23-25,27,29-38,44H2,1-2H3,(H,47,48)/b7-5-,13-11-,14-12-,18-17-,22-20-,28-26-/t39-,40?,41?/m1/s1
InChI KeyPVVBUTMNSJLVOU-DAVMKAPESA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effect
Disposition
Process
Role
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
logP7.78ALOGPS
logP9.65ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area146.91 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity224.83 m³·mol⁻¹ChemAxon
Polarizability90.32 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]+282.33232859911
AllCCS[M+H-H2O]+282.24632859911
AllCCS[M+Na]+282.38532859911
AllCCS[M+NH4]+282.37832859911
AllCCS[M-H]-273.10632859911
AllCCS[M+Na-2H]-280.11732859911
AllCCS[M+HCOO]-287.82632859911
DeepCCS[M+H]+269.37530932474
DeepCCS[M-H]-267.06430932474
DeepCCS[M-2H]-300.30530932474
DeepCCS[M+Na]+275.11530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6))[H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OCCN)OC(=O)CCCC1OC1C\C=C/C\C=C/C\C=C/CCCCC5583.4Standard polar33892256
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6))[H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OCCN)OC(=O)CCCC1OC1C\C=C/C\C=C/C\C=C/CCCCC4965.6Standard non polar33892256
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6))[H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OCCN)OC(=O)CCCC1OC1C\C=C/C\C=C/C\C=C/CCCCC5433.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)),1TMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCC1OC1C/C=C\C/C=C\C/C=C\CCCCC5509.4Semi standard non polar33892256
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)),1TMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCC1OC1C/C=C\C/C=C\C/C=C\CCCCC4672.8Standard non polar33892256
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)),1TMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCC1OC1C/C=C\C/C=C\C/C=C\CCCCC6655.8Standard polar33892256
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)),1TMS,isomer #2CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCC1OC1C/C=C\C/C=C\C/C=C\CCCCC5631.7Semi standard non polar33892256
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)),1TMS,isomer #2CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCC1OC1C/C=C\C/C=C\C/C=C\CCCCC4986.6Standard non polar33892256
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)),1TMS,isomer #2CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCC1OC1C/C=C\C/C=C\C/C=C\CCCCC6469.0Standard polar33892256
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)),1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)OC(=O)CCCC1OC1C/C=C\C/C=C\C/C=C\CCCCC5730.3Semi standard non polar33892256
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)),1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)OC(=O)CCCC1OC1C/C=C\C/C=C\C/C=C\CCCCC4737.7Standard non polar33892256
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)),1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)OC(=O)CCCC1OC1C/C=C\C/C=C\C/C=C\CCCCC6619.2Standard polar33892256
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)),1TBDMS,isomer #2CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)OC(=O)CCCC1OC1C/C=C\C/C=C\C/C=C\CCCCC5843.0Semi standard non polar33892256
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)),1TBDMS,isomer #2CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)OC(=O)CCCC1OC1C/C=C\C/C=C\C/C=C\CCCCC5083.4Standard non polar33892256
PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)),1TBDMS,isomer #2CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)OC(=O)CCCC1OC1C/C=C\C/C=C\C/C=C\CCCCC6392.5Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)) 10V, Negative-QTOFsplash10-004i-0011000900-90e3d9d3de264eecee942021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)) 20V, Negative-QTOFsplash10-004i-0011000900-90e3d9d3de264eecee942021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)) 40V, Negative-QTOFsplash10-00or-0399410600-ddf7a41d106f6124f56d2021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)) 10V, Positive-QTOFsplash10-004i-0000001900-516b988e58467887269d2021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)) 20V, Positive-QTOFsplash10-002r-0003339700-920f308cca9949531be92021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)) 40V, Positive-QTOFsplash10-000i-0003339300-c85ced374d2da3ee59392021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)) 10V, Positive-QTOFsplash10-0udi-0000001090-d52a5f04703b590f82d62021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)) 20V, Positive-QTOFsplash10-0zfr-0000002290-611d1f656624209c75d12021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)-O(5,6)) 40V, Positive-QTOFsplash10-0a4i-0100301910-d24606f516a8bcfe3a142021-09-28Wishart 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 43 proteins in total.

Enzymes

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 metabolic process
Specific function:
Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:
PLA2G6
Uniprot ID:
O60733
Molecular weight:
84092.635
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. L-alpha-1-palmitoyl-2-linoleoyl phosphatidylethanolamine is more efficiently hydrolyzed than the other phospholipids examined.
Gene Name:
PLA2G2D
Uniprot ID:
Q9UNK4
Molecular weight:
16546.1
General function:
Involved in protein binding
Specific function:
May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:
PLD2
Uniprot ID:
O14939
Molecular weight:
104656.485

Only showing the first 10 proteins. There are 43 proteins in total.