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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-16 01:08:44 UTC
Update Date2022-11-30 20:06:59 UTC
HMDB IDHMDB0290061
Secondary Accession NumbersNone
Metabolite Identification
Common NameCer(d18:2(4E,14Z)/PGJ2)
DescriptionCer(d18:2(4E,14Z)/PGJ2) is an oxidized ceramide (Cer). As all ceramides, oxidized ceramides are members of the class of compounds known as sphingolipids (SPs), or glycosylceramides. SPs are lipids containing a backbone of sphingoid bases (e.g. sphingosine or sphinganine) that are often covalently bound to a fatty acid derivative through N-acylation. SPs are found in cell membranes, particularly in peripheral nerve cells and the cells found in the central nervous system (including the brain and spinal cord). Sphingolipids are extremely versatile molecules that have functions controlling fundamental cellular processes such as cell division, differentiation, and cell death. Impairments associated with sphingolipid metabolism are associated with many common human diseases such as diabetes, various cancers, microbial infections, diseases of the cardiovascular and respiratory systems, Alzheimer’s disease and other neurological syndromes. The biosynthesis and catabolism of sphingolipids involves a large number of intermediate metabolites where many different enzymes are involved. Simple sphingolipids, which include the sphingoid bases and ceramides, make up the early products of the sphingolipid synthetic pathways, while complex sphingolipids may be formed by the addition of head groups to the ceramide template (Wikipedia). In humans, ceramides are phosphorylated to ceramide phosphates (CerPs) through the action of a specific ceramide kinase (CerK). Ceramide phosphates are important metabolites of ceramides as they act as a mediators of the inflammatory response. Ceramides are also one of the hydrolysis byproducts of sphingomyelins (SMs) through the action of the enzyme sphingomyelin phosphodiesterase, which has been identified in the subcellular fractions of human epidermis (PMID: 25935) and many other tissues. Ceramides can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID: 14998372). Ceramides are key in the biosynthesis of glycosphingolipids and gangliosides. In terms of its appearance and structure, Cer(d18:1/22:1(13Z)) is a colorless solid that consists of an unsaturated 18-carbon sphingoid base with an attached unsaturated 13Z-docosenoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481).
Structure
Thumb
Synonyms
ValueSource
(5Z)-N-[(2S,3R,14Z)-1,3-Dihydroxyoctadeca-4,14-dien-2-yl]-7-[(1S,5R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-4-oxocyclopent-2-en-1-yl]hept-5-enimidateGenerator
Chemical FormulaC38H63NO5
Average Molecular Weight613.924
Monoisotopic Molecular Weight613.470624133
IUPAC Name(5Z)-N-[(2S,3R,4E,14Z)-1,3-dihydroxyoctadeca-4,14-dien-2-yl]-7-[(1S,5R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-4-oxocyclopent-2-en-1-yl]hept-5-enamide
Traditional Name(5Z)-N-[(2S,3R,4E,14Z)-1,3-dihydroxyoctadeca-4,14-dien-2-yl]-7-[(1S,5R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-4-oxocyclopent-2-en-1-yl]hept-5-enamide
CAS Registry NumberNot Available
SMILES
CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(=O)N[C@@H](CO)[C@H](O)\C=C\CCCCCCCC\C=C/CCC)C=CC1=O
InChI Identifier
InChI=1S/C38H63NO5/c1-3-5-7-8-9-10-11-12-13-14-15-16-21-25-37(43)35(31-40)39-38(44)26-22-18-17-20-23-32-27-30-36(42)34(32)29-28-33(41)24-19-6-4-2/h7-8,17,20-21,25,27-30,32-35,37,40-41,43H,3-6,9-16,18-19,22-24,26,31H2,1-2H3,(H,39,44)/b8-7-,20-17-,25-21+,29-28+/t32-,33-,34+,35-,37+/m0/s1
InChI KeyIYLCOWZQNCVHMN-XZPCDGKYSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effect
Disposition
Process
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
logP7.32ALOGPS
logP8.62ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)13.53ChemAxon
pKa (Strongest Basic)-0.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 ŲChemAxon
Rotatable Bond Count27ChemAxon
Refractivity188.9 m³·mol⁻¹ChemAxon
Polarizability76.06 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]+256.35832859911
AllCCS[M+H-H2O]+255.77132859911
AllCCS[M+Na]+257.00732859911
AllCCS[M+NH4]+256.86732859911
AllCCS[M-H]-237.72332859911
AllCCS[M+Na-2H]-243.19532859911
AllCCS[M+HCOO]-249.30432859911
DeepCCS[M+H]+262.3330932474
DeepCCS[M-H]-260.50630932474
DeepCCS[M-2H]-293.7530932474
DeepCCS[M+Na]+267.93630932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:2(4E,14Z)/PGJ2) 10V, Positive-QTOFsplash10-004j-1000091000-3f4297e1b9aa6e195ec92021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:2(4E,14Z)/PGJ2) 20V, Positive-QTOFsplash10-003r-6260390000-04273c22535e19134d582021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:2(4E,14Z)/PGJ2) 40V, Positive-QTOFsplash10-001i-9660100000-f6e2b55fe4a2202de1062021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:2(4E,14Z)/PGJ2) 10V, Negative-QTOFsplash10-03di-0000049000-e661ed956d5600b0e5852021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:2(4E,14Z)/PGJ2) 20V, Negative-QTOFsplash10-03dl-2249167000-a7a8a1f4393954fddb022021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(d18:2(4E,14Z)/PGJ2) 40V, Negative-QTOFsplash10-0bu9-3289131000-c5e08761520796438f122021-10-21Wishart 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 ReferencesNot Available