Cer(d18:1/23:0) (CHEM035005)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:24:42 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM035005
Identification
Common NameCer(d18:1/23:0)
ClassSmall Molecule
DescriptionCer(d18:1/23:0) is an sphingolipid identified in stratum corneum by reversed-phase high-performance liquid chromatography photospray ionization mass spectrometry. Tricosanamide has been found in human blood plasma by gas-liquid chromatography on high temperature polarizable capillary columns. Tricosanamide is a molecular species of lipid determined in human erythrocytes. (PMID: 2755317, 17027012, 8354950)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-(Tricosanoyl)-sphing-4-enineChEBI
N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-tricosanamideHMDB
N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-tricosanamideHMDB
[R-[R*,s*-(e)]]-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-tricosanamideHMDB
CeramideHMDB
Ceramide(D18:1/23:0)HMDB
N-(Tricosanoyl)-sphingosineHMDB
N-(Tricosanoyl)-D-erythro-sphingosineHMDB
N-(Tricosanoyl)-4-sphingenineHMDB
N-(Tricosanoyl)-D-sphingosineHMDB
N-(Tricosanoyl)-sphingenineHMDB
N-(Tricosanoyl)-erythro-4-sphingenineHMDB
C23-CeramideHMDB
Ceramide (D18:1,C23:0)HMDB
Cer(d18:1/23:0)HMDB
Chemical FormulaC41H81NO3
Average Molecular Mass636.087 g/mol
Monoisotopic Mass635.622 g/mol
CAS Registry Number67605-84-9
IUPAC NameN-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]tricosanamide
Traditional NameN-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]tricosanamide
SMILESCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)\C=C\CCCCCCCCCCCCC
InChI IdentifierInChI=1S/C41H81NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-27-29-31-33-35-37-41(45)42-39(38-43)40(44)36-34-32-30-28-26-24-16-14-12-10-8-6-4-2/h34,36,39-40,43-44H,3-33,35,37-38H2,1-2H3,(H,42,45)/b36-34+/t39-,40+/m0/s1
InChI KeyNAJHAHQNQCNWOP-PUYNVXOJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassCeramides
Direct ParentCeramides
Alternative Parents
Substituents
  • Ceramide
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.4e-05 g/LALOGPS
logP10.29ALOGPS
logP13.98ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity197.98 m³·mol⁻¹ChemAxon
Polarizability87.82 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Cer(d18:1/23:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-d3e8008e7ba10d1c9431Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-0050009000-3766eaf41ece7db39bd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03yi-0090005000-316946107e778fc6c5c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-69b22ff17c52e418bc5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000009000-69b22ff17c52e418bc5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0000019000-c93b2a0832c74ef383c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-1c5e364871a24ca4de3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-0050009000-711372eb4f19c91232aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03yi-0090005000-3619fb0d2f7f784c5aabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000009000-2562d89123b514c86209Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0010009000-ae5f9ceed10a79756196Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uf0-0022009000-370d4c24617096ced0abSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000950
FooDB IDFDB022334
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5896
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24765757
ChEBI ID84372
PubChem Compound ID52931115
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Gaudin, K.; Lesellier, E.; Chaminade, P.; Ferrier, D.; Baillet, A.; Tchapla, A. Retention behaviour of ceramides in sub-critical fluid chromatography in comparison with non-aqueous reversed-phase liquid chromatography. Journal of Chromatography, A (2000), 883(1+2), 211-222
2. Myher JJ, Kuksis A, Pind S: Molecular species of glycerophospholipids and sphingomyelins of human erythrocytes: improved method of analysis. Lipids. 1989 May;24(5):396-407.
3. Munoz-Garcia A, Ro J, Brown JC, Williams JB: Identification of complex mixtures of sphingolipids in the stratum corneum by reversed-phase high-performance liquid chromatography and atmospheric pressure photospray ionization mass spectrometry. J Chromatogr A. 2006 Nov 10;1133(1-2):58-68. Epub 2006 Oct 5.
4. Kuksis A, Myher JJ, Geher K: Quantitation of plasma lipids by gas-liquid chromatography on high temperature polarizable capillary columns. J Lipid Res. 1993 Jun;34(6):1029-38.
5. Bowser PA, Gray GM: Sphingomyelinase in pig and human epidermis. J Invest Dermatol. 1978 Jun;70(6):331-5.
6. Tserng KY, Griffin RL: Ceramide metabolite, not intact ceramide molecule, may be responsible for cellular toxicity. Biochem J. 2004 Jun 15;380(Pt 3):715-22.