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Showing Compound Ceramide (d18:1/22:0) (FDB023539)

Record Information
Version1.0
Creation date2011-09-21 00:31:20 UTC
Update date2017-03-11 23:00:27 UTC
Primary IDFDB023539
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCeramide (d18:1/22:0)
DescriptionCeramides (N-acylsphingosine) are one of the hydrolysis byproducts of sphingomyelin by the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis (PMID 25935) and many other tissues. They 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). Is key in the biosynthesis of glycosphingolipids and gangliosides. [HMDB]
CAS Number104404-17-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
C22 CerChEBI
Cer(d18:1/22:0)ChEBI
N-(Docosanoyl)-sphing-4-enineChEBI
N-(Docosanoyl)ceramideChEBI
N-(Docosanoyl)sphing-4-enineChEBI
N-BehenoylsphingosineChEBI
N-Docosanoylsphing-4-enineChEBI
(2S,3R,4E)-2-acylamino-1,3-Octadec-4-enediolHMDB
(2S,3R,4E)-2-Acylaminooctadec-4-ene-1,3-diolHMDB
CerHMDB
CeramideHMDB
N-AcylsphingosineHMDB
N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-octadecanamideHMDB
Ceramide (d18:1/22:0)ChEBI
C22-CeramideHMDB
Cer d18:1/22:0HMDB
Ceramide (d18:1,C22:0)HMDB
Ceramide 22HMDB
Ceramide(d18:1/22:0)HMDB
N-Docosanoyl-C18-sphingosineHMDB
Cer(D18:1/22:0)ChEBI
Predicted Properties
PropertyValueSource
Water Solubility2.5e-05 g/LALOGPS
logP10.21ALOGPS
logP13.53ChemAxon
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 Count36ChemAxon
Refractivity193.38 m³·mol⁻¹ChemAxon
Polarizability86.09 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC40H79NO3
IUPAC nameN-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]docosanamide
InChI IdentifierInChI=1S/C40H79NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-40(44)41-38(37-42)39(43)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h33,35,38-39,42-43H,3-32,34,36-37H2,1-2H3,(H,41,44)/b35-33+/t38-,39+/m0/s1
InChI KeyKEPQASGDXIEOIL-GLQCRSEXSA-N
Isomeric SMILESCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)\C=C\CCCCCCCCCCCCC
Average Molecular Weight622.0602
Monoisotopic Molecular Weight621.605995399
Classification
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
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
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 (d18:1/22:0), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dr-4082449000-570258ec8b5b7ded96bcSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000009000-1e19b87d54d58e0231732017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-0050009000-34f7ce2aa3a396fe64372017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0il0-0090014000-03b335fc70e62035e6f42017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000009000-a1f74db65a0e64aa28592021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0010009000-2a9dcc90b128b770e6ee2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e0-0044099000-d217f4d61f402a9c0f0f2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000009000-e80ce596d203b4ebd9542021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-0050009000-d1856bd41514ed2bb08c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0il0-0090014000-9e42e3b0d27d4e1aa2442021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000009000-a6c3c6cf724cb20eac0b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000009000-a6c3c6cf724cb20eac0b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000019000-f17b53e24bfab1f289ba2021-09-25View Spectrum
NMRNot Available
ChemSpider ID4446680
ChEMBL IDNot Available
KEGG Compound IDC00195
Pubchem Compound ID5283567
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04952
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
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
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
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference