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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-16 01:57:07 UTC
Update Date2022-11-30 20:07:03 UTC
HMDB IDHMDB0290184
Secondary Accession NumbersNone
Metabolite Identification
Common NameCer(t18:0/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15))
DescriptionCer(t18:0/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) 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
(5R,6R,7Z,9Z,11E,13E,15S,17Z)-5,6,15-Trihydroxy-N-[(2S,3S,4S)-1,3,4-trihydroxyoctadecan-2-yl]icosa-7,9,11,13,17-pentaenimidateGenerator
Chemical FormulaC38H67NO7
Average Molecular Weight649.954
Monoisotopic Molecular Weight649.491753501
IUPAC Name(5R,6R,7Z,9Z,11E,13E,15S,17Z)-5,6,15-trihydroxy-N-[(2S,3S,4S)-1,3,4-trihydroxyoctadecan-2-yl]icosa-7,9,11,13,17-pentaenamide
Traditional Name(5R,6R,7Z,9Z,11E,13E,15S,17Z)-5,6,15-trihydroxy-N-[(2S,3S,4S)-1,3,4-trihydroxyoctadecan-2-yl]icosa-7,9,11,13,17-pentaenamide
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(NC(=O)CCC[C@@H](O)[C@H](O)\C=C/C=C\C=C\C=C\[C@@H](O)C\C=C/CC)[C@H](O)[C@@H](O)CCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C38H67NO7/c1-3-5-7-8-9-10-11-12-13-14-19-23-28-36(44)38(46)33(31-40)39-37(45)30-24-29-35(43)34(42)27-22-18-16-15-17-21-26-32(41)25-20-6-4-2/h6,15-18,20-22,26-27,32-36,38,40-44,46H,3-5,7-14,19,23-25,28-31H2,1-2H3,(H,39,45)/b17-15+,18-16-,20-6-,26-21+,27-22-/t32-,33-,34+,35+,36-,38-/m0/s1
InChI KeyONXBPUCMEJMJPE-MTQHXEKCSA-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
logP5.97ALOGPS
logP6.43ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)13.06ChemAxon
pKa (Strongest Basic)-0.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area150.48 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity194.55 m³·mol⁻¹ChemAxon
Polarizability80.72 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]+265.82632859911
AllCCS[M+H-H2O]+265.33132859911
AllCCS[M+Na]+266.36732859911
AllCCS[M+NH4]+266.25232859911
AllCCS[M-H]-259.22132859911
AllCCS[M+Na-2H]-264.76132859911
AllCCS[M+HCOO]-270.93632859911
DeepCCS[M+H]+256.15230932474
DeepCCS[M-H]-254.32730932474
DeepCCS[M-2H]-287.84230932474
DeepCCS[M+Na]+261.75730932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(t18:0/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) 10V, Positive-QTOFsplash10-03e9-0000019000-ef4145bd5e8a5d7a796a2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(t18:0/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) 20V, Positive-QTOFsplash10-03dr-4143229000-c656176516567d5dd5762021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(t18:0/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) 40V, Positive-QTOFsplash10-0aor-6695201000-8b7e800e6fffbaa93f192021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(t18:0/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) 10V, Negative-QTOFsplash10-0002-0001009000-422e0bfbfbc312b836932021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(t18:0/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) 20V, Negative-QTOFsplash10-0ue9-0014409000-26ccf5da4dbb6e52d4ed2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cer(t18:0/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) 40V, Negative-QTOFsplash10-00fr-3239101000-875b309ed673b311cb612021-10-21Wishart 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