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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-13 16:35:14 UTC
Update Date2022-11-30 20:03:07 UTC
HMDB IDHMDB0281352
Secondary Accession NumbersNone
Metabolite Identification
Common NamePS(18:0/LTE4)
DescriptionPS(18:0/LTE4) is an oxidized phosphatidylserine (PS). Oxidized phosphatidylserines are glycerophospholipids in which a phosphorylserine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylserines 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, phosphatidylserines 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. PS(18:0/LTE4), in particular, consists of one chain of one octadecanoyl at the C-1 position and one chain of Leukotriene E4 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 PSs can be synthesized via three different routes. In one route, the oxidized PS is synthetized de novo following the same mechanisms as for PSs 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 PS backbone, mainly through the action of LOX (PMID: 33329396 ).
Structure
Thumb
Synonyms
ValueSource
(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-3-{[(2R)-1-({[(2S)-2-amino-2-carboxyethoxy](hydroxy)phosphoryl}oxy)-3-(octadecanoyloxy)propan-2-yl]oxy}-3-oxopropyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoateGenerator
(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-3-{[(2R)-1-({[(2S)-2-amino-2-carboxyethoxy](hydroxy)phosphoryl}oxy)-3-(octadecanoyloxy)propan-2-yl]oxy}-3-oxopropyl]sulphanyl}-5-hydroxyicosa-7,9,11,14-tetraenoateGenerator
(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-3-{[(2R)-1-({[(2S)-2-amino-2-carboxyethoxy](hydroxy)phosphoryl}oxy)-3-(octadecanoyloxy)propan-2-yl]oxy}-3-oxopropyl]sulphanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acidGenerator
Chemical FormulaC47H83N2O13PS
Average Molecular Weight947.22
Monoisotopic Molecular Weight946.535348913
IUPAC Name(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-3-{[(2R)-1-({[(2S)-2-amino-2-carboxyethoxy](hydroxy)phosphoryl}oxy)-3-(octadecanoyloxy)propan-2-yl]oxy}-3-oxopropyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid
Traditional Name(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-3-{[(2R)-1-{[(2S)-2-amino-2-carboxyethoxy(hydroxy)phosphoryl]oxy}-3-(octadecanoyloxy)propan-2-yl]oxy}-3-oxopropyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)[C@@H](N)CS[C@H](\C=C\C=C\C=C/C\C=C/CCCCC)[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C47H83N2O13PS/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-34-45(53)59-35-39(36-60-63(57,58)61-37-40(48)46(54)55)62-47(56)41(49)38-64-43(42(50)31-30-33-44(51)52)32-28-26-24-22-20-16-14-12-10-8-6-4-2/h12,14,20,22,24,26,28,32,39-43,50H,3-11,13,15-19,21,23,25,27,29-31,33-38,48-49H2,1-2H3,(H,51,52)(H,54,55)(H,57,58)/b14-12-,22-20-,26-24+,32-28+/t39-,40+,41+,42+,43-/m1/s1
InChI KeyMHTVXMFACAYDIM-LRWZVMIOSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effectNot Available
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
logP2.68ALOGPS
logP4.91ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)1.47ChemAxon
pKa (Strongest Basic)9.38ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area255.23 ŲChemAxon
Rotatable Bond Count46ChemAxon
Refractivity256.57 m³·mol⁻¹ChemAxon
Polarizability107.97 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]+315.69732859911
AllCCS[M+H-H2O]+315.98432859911
AllCCS[M+Na]+315.30632859911
AllCCS[M+NH4]+315.39832859911
AllCCS[M-H]-297.57832859911
AllCCS[M+Na-2H]-304.29632859911
AllCCS[M+HCOO]-311.63132859911
DeepCCS[M+H]+301.86630932474
DeepCCS[M-H]-300.14330932474
DeepCCS[M-2H]-334.17430932474
DeepCCS[M+Na]+308.13630932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:0/LTE4) 10V, Positive-QTOFsplash10-0002-0000000109-ef98dbf353386f6a9df12021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:0/LTE4) 20V, Positive-QTOFsplash10-03dj-0001133916-cb78c18e3508265be2fe2021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:0/LTE4) 40V, Positive-QTOFsplash10-03di-0001133911-05a958444370e43e4c522021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:0/LTE4) 10V, Positive-QTOFsplash10-0yvi-0000000999-fe2bdbd9d65c2576bf022021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:0/LTE4) 20V, Positive-QTOFsplash10-0yvo-0900000999-501b8874b9c9ec46f27a2021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:0/LTE4) 40V, Positive-QTOFsplash10-0yvo-0900000999-501b8874b9c9ec46f27a2021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:0/LTE4) 10V, Negative-QTOFsplash10-0002-0000000009-7c39046e53cdab9f33022021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:0/LTE4) 20V, Negative-QTOFsplash10-0002-0000000019-07bf4f96406a2a9272892021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:0/LTE4) 40V, Negative-QTOFsplash10-0awj-0130950053-575e378d0c6da9028d4f2021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:0/LTE4) 10V, Positive-QTOFsplash10-0159-0000000169-5762c0d138d082309e482021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:0/LTE4) 20V, Positive-QTOFsplash10-014i-0000000029-696cce636daf62f6a35a2021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:0/LTE4) 40V, Positive-QTOFsplash10-0a4i-0090000331-dc03231dae09a140a5032021-09-28Wishart 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 ]