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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-16 19:01:17 UTC
Update Date2022-11-30 20:07:19 UTC
HMDB IDHMDB0290799
Secondary Accession NumbersNone
Metabolite Identification
Common NameCDP-DG(LTE4/16:0)
DescriptionCDP-DG(LTE4/16:0) is an oxidized CDP-diacylglycerol (CDP-DG). Oxidized CDP-diacylglycerols are glycerophospholipids in which a cytidine diphosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized CDP-diacylglycerols 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, CDP-diacylglycerols 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. CDP-DG(LTE4/16:0), in particular, consists of one chain of one Leukotriene E4 at the C-1 position and one chain of hexadecanoyl 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 CDP-DGs can be synthesized via three different routes. In one route, the oxidized CDP-DG is synthetized de novo following the same mechanisms as for CDP-DGs 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 CDP-DG 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)-3-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-(hexadecanoyloxy)propoxy]-3-oxopropyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoateGenerator
(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-3-[(2R)-3-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-(hexadecanoyloxy)propoxy]-3-oxopropyl]sulphanyl}-5-hydroxyicosa-7,9,11,14-tetraenoateGenerator
(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-3-[(2R)-3-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-(hexadecanoyloxy)propoxy]-3-oxopropyl]sulphanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acidGenerator
Chemical FormulaC51H86N4O18P2S
Average Molecular Weight1137.27
Monoisotopic Molecular Weight1136.513307115
IUPAC Name(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-3-[(2R)-3-({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-(hexadecanoyloxy)propoxy]-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)-3-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-(hexadecanoyloxy)propoxy]-3-oxopropyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)[C@@H](N)CS[C@H](\C=C\C=C\C=C/C\C=C/CCCCC)[C@@H](O)CCCC(O)=O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O
InChI Identifier
InChI=1S/C51H86N4O18P2S/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-32-46(59)71-39(36-69-74(64,65)73-75(66,67)70-37-42-47(60)48(61)49(72-42)55-34-33-44(53)54-51(55)63)35-68-50(62)40(52)38-76-43(41(56)29-28-31-45(57)58)30-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,22,24,26,30,33-34,39-43,47-49,56,60-61H,3-11,13,15-17,19,21,23,25,27-29,31-32,35-38,52H2,1-2H3,(H,57,58)(H,64,65)(H,66,67)(H2,53,54,63)/b14-12-,20-18-,24-22+,30-26+/t39-,40+,41+,42-,43-,47-,48-,49-/m1/s1
InChI KeyYDTJCPGKMSSONP-ZKFQIUSPSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
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
logP3.17ALOGPS
logP6.43ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)-0.032ChemAxon
pKa (Strongest Basic)7.03ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area346.82 ŲChemAxon
Rotatable Bond Count46ChemAxon
Refractivity290.75 m³·mol⁻¹ChemAxon
Polarizability120.62 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]+333.61232859911
AllCCS[M+H-H2O]+334.17632859911
AllCCS[M+Na]+332.8932859911
AllCCS[M+NH4]+333.05632859911
AllCCS[M-H]-300.72432859911
AllCCS[M+Na-2H]-307.01632859911
AllCCS[M+HCOO]-313.81632859911
DeepCCS[M+H]+330.35630932474
DeepCCS[M-H]-328.46130932474
DeepCCS[M-2H]-362.23430932474
DeepCCS[M+Na]+336.25330932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(LTE4/16:0) 10V, Positive-QTOFsplash10-0uy0-2659000000-b7277360b6b01937d5292021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(LTE4/16:0) 20V, Positive-QTOFsplash10-00lj-3902000000-4e1c1eda42195297ef932021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(LTE4/16:0) 40V, Positive-QTOFsplash10-00or-5900000000-70403561c8d2298bbd4b2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(LTE4/16:0) 10V, Negative-QTOFsplash10-000i-1900000010-35929b3dd0e12856a51e2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(LTE4/16:0) 20V, Negative-QTOFsplash10-01q9-2439000000-0086130aca73d4c22e562021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(LTE4/16:0) 40V, Negative-QTOFsplash10-0f89-5968010100-1d3aa82babe035f333832021-10-21Wishart 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 ]