Record Information
Version1.0
Creation date2011-09-21 00:31:18 UTC
Update date2015-07-21 06:57:45 UTC
Primary IDFDB023536
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCeramide (d18:1/16:0)
DescriptionCer(d18:1/16:0), also known as N-hexadecanoyl-sphing-4-enine, is a ceramide (Cer). 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(d18:1/16:0) is a colorless solid that consists of an unsaturated 18-carbon sphingoid base with an attached saturated hexadecanoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481).
CAS Number4201-58-5
Structure
Thumb
Synonyms
SynonymSource
(2S,3R,4E)-2-Acylamino-1,3-octadec-4-enediolChEBI
(2S,3R,4E)-2-Acylaminooctadec-4-ene-1,3-diolChEBI
C16 CerChEBI
C16 CeramideChEBI
C16-0(Palmitoyl)ceramideChEBI
Ceramide (D18:1/16:0)ChEBI
N-(Hexadecanoyl)-sphing-4-enineChEBI
N-(Hexadecanoyl)ceramideChEBI
N-(Hexadecanoyl)sphing-4-enineChEBI
N-(Palmitoyl)ceramideChEBI
N-Hexadecanoyl-D-erythro-sphingosineChEBI
N-Hexadecanoylsphing-4-enineChEBI
N-Palmitoyl-sphingosineChEBI
N-Palmitoylsphing-4-enineChEBI
N-PalmitoylsphingosineChEBI
CerHMDB
CeramideHMDB
N-AcylsphingosineHMDB
N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-octadecanamideHMDB
C16-CeramideHMDB
NFA(C16)cerHMDB
PalmitoylceramideHMDB
C(16)-CeramideHMDB
N-Palmitoylsphingosine, (r*,s*-(e))-(+-)HMDB
C16-PalmitoylceramideHMDB
N-Palmitoylsphingosine, R-(r*,s*-(e))HMDB
PCer CPDHMDB
Ceramide-C16HMDB
(2S,3R,4E)-2-N-Palmitoyloctadecasphinga-4-eneHMDB
C16:0-CeramideHMDB
Ceramide (D18:1,C16:0)HMDB
Ceramide 16HMDB
Ceramide(D18:1/16:0)HMDB
D-Erythro-C16-ceramideHMDB
D-Erythro-N-hexadecanoylsphingenineHMDB
D-Erythro-N-palmitoylsphingosineHMDB
D-Erythro-delta4-ceramideHMDB
D-Erythro-δ4-ceramideHMDB
N-Hexadecanoyl-D-erythro-ceramideHMDB
N-HexadecanoylsphingosineHMDB
N-Palmitoyl 4-sphingenineHMDB
N-Palmitoyl ceramideHMDB
N-Palmitoyl-D-erythro-sphingosineHMDB
N-Palmitoyl-D-sphingosineHMDB
N-(Hexadecanoyl)-sphingosineMetBuilder
N-(Hexadecanoyl)-D-erythro-sphingosineMetBuilder
N-(Hexadecanoyl)-4-sphingenineMetBuilder
N-(Hexadecanoyl)-D-sphingosineMetBuilder
N-(Hexadecanoyl)-sphingenineMetBuilder
N-(Hexadecanoyl)-erythro-4-sphingenineMetBuilder
Cer(D18:1/16:0)ChEBI
Predicted Properties
PropertyValueSource
Water Solubility4.1e-05 g/LALOGPS
logP9.49ALOGPS
logP10.87ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity165.78 m³·mol⁻¹ChemAxon
Polarizability73.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC34H67NO3
IUPAC nameN-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide
InChI IdentifierInChI=1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/b29-27+/t32-,33+/m0/s1
InChI KeyYDNKGFDKKRUKPY-TURZORIXSA-N
Isomeric SMILESCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)\C=C\CCCCCCCCCCCCC
Average Molecular Weight537.9007
Monoisotopic Molecular Weight537.512095015
Classification
Description Belongs to the class of organic compounds known as long-chain ceramides. These are ceramides bearing a long chain fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassCeramides
Direct ParentLong-chain ceramides
Alternative Parents
Substituents
  • Long-chain 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
Ontology
Physiological effect

Health effect:

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCeramide (d18:1/16:0), 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00y0-4371679000-4350654880fad493e81dSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090020000-a4c08ce2d2d5bc07212cSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090020000-6b6cc500a909ad02bd59Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090020000-4a672523b98af8ff8c7cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000090000-f294f0ced8f149249815Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-0050090000-80f4b14827e42ec58feaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03l0-0090050000-c9f32bf831226119babdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000090000-876883608819d763f04eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-0050090000-22ff2434faf08fcef599Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03l0-0090050000-e6a7f6704ac5e854065cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000090000-15b6716e7356e06043b6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0010090000-e14e9c0c2e28b7a12b19Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue0-0040090000-a44d6a95bf21d0975da6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000090000-d2d11b266d3c5c7e73ffSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000090000-d2d11b266d3c5c7e73ffSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0000190000-6ce0a8c6d5140383d837Spectrum
NMRNot Available
ChemSpider ID4446677
ChEMBL IDCHEMBL35292
KEGG Compound IDC00195
Pubchem Compound ID5283564
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04949
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID16C
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Lactase-phlorizin hydrolaseLCTP09848
GlucosylceramidaseGBAP04062
Probable leucine--tRNA ligase, mitochondrialLARS2Q15031
Leucine--tRNA ligase, cytoplasmicLARSQ9P2J5
Acid ceramidaseASAH1Q13510
Putative neutral ceramidase CASAH2CP0C7U2
Alkaline ceramidase 2ACER2Q5QJU3
Neutral ceramidaseASAH2Q9NR71
Alkaline ceramidase 1ACER1Q8TDN7
Phosphatidylcholine:ceramide cholinephosphotransferase 2SGMS2Q8NHU3
Phosphatidylcholine:ceramide cholinephosphotransferase 1SGMS1Q86VZ5
Ganglioside GM2 activatorGM2AP17900
Sphingosine-1-phosphate lyase 1SGPL1O95470
GalactocerebrosidaseGALCP54803
N-acetylglucosaminyl-phosphatidylinositol de-N-acetylasePIGLQ9Y2B2
Sphingomyelin phosphodiesteraseSMPD1P17405
Ceramide glucosyltransferaseUGCGQ16739
Phosphatidylinositol N-acetylglucosaminyltransferase subunit QPIGQQ9BRB3
Phosphatidylinositol N-acetylglucosaminyltransferase subunit APIGAP37287
Phosphatidylinositol N-acetylglucosaminyltransferase subunit HPIGHQ14442
Phosphatidylinositol N-acetylglucosaminyltransferase subunit PPIGPP57054
Phosphatidylinositol N-acetylglucosaminyltransferase subunit CPIGCQ92535
2-hydroxyacylsphingosine 1-beta-galactosyltransferaseUGT8Q16880
Collagen type IV alpha-3-binding proteinCOL4A3BPQ9Y5P4
T-cell surface glycoprotein CD1e, membrane-associatedCD1EP15812
Epididymal secretory protein E1NPC2P61916
Ceramide synthase 1CERS1P27544
Antigen-presenting glycoprotein CD1dCD1DP15813
GPI mannosyltransferase 1PIGMQ9H3S5
Phosphatidylinositol-glycan biosynthesis class W proteinPIGWQ7Z7B1
Phosphatidylinositol-glycan biosynthesis class X proteinPIGXQ8TBF5
GPI mannosyltransferase 4PIGZQ86VD9
Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferaseB3GNT5Q9BYG0
Beta-1,3-galactosyltransferase 5B3GALT5Q9Y2C3
GPI mannosyltransferase 3PIGBQ92521
Phosphatidylinositol-glycan biosynthesis class F proteinPIGFQ07326
GPI ethanolamine phosphate transferase 2PIGGQ5H8A4
GPI ethanolamine phosphate transferase 1PIGNO95427
GPI ethanolamine phosphate transferase 3PIGOQ8TEQ8
GPI transamidase component PIG-SPIGSQ96S52
GPI transamidase component PIG-TPIGTQ969N2
Phosphatidylinositol glycan anchor biosynthesis class U proteinPIGUQ9H490
GPI mannosyltransferase 2PIGVQ9NUD9
Phosphatidylinositol N-acetylglucosaminyltransferase subunit YPIGYQ3MUY2
Non-lysosomal glucosylceramidaseGBA2Q9HCG7
Protein FANNSMAFQ92636
GPI-anchor transamidasePIGKQ92643
Methylcrotonoyl-CoA carboxylase beta chain, mitochondrialMCCC2Q9HCC0
Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrialMCCC1Q96RQ3
Methylglutaconyl-CoA hydratase, mitochondrialAUHQ13825
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference