Lactosylceramide (d18:1/24:0) (CHEM040361)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 20:34:36 UTC
Update Date2016-11-09 01:22:14 UTC
Accession NumberCHEM040361
Identification
Common NameLactosylceramide (d18:1/24:0)
ClassSmall Molecule
DescriptionLactosylceramide (d18:1/24:0) is a lactosylceramide or LacCer. Lactosylceramides are the most important and abundant of the diosylceramides. Lactosylceramides (LacCer) were originally called 'cytolipin H'. It is found in small amounts only in most animal tissues, but it has a number of significant biological functions and it is of great importance as the biosynthetic precursor of most of the neutral oligoglycosylceramides, sulfatides and gangliosides. In animal tissues, biosynthesis of lactosylceramide involves addition of the second monosaccharides unit (galactose) as its nucleotide derivative to monoglucosylceramide, catalysed by a specific beta-1,4-galactosyltransferase on the lumenal side of the Golgi apparatus. The glucosylceramide precursor must first cross from the cytosolic side of the membrane, possibly via the action of a flippase. The lactosylceramide produced can be further glycosylated or transferred to the plasma membrane. Lactosylceramide may assist in stabilizing the plasma membrane and activating receptor molecules in the special micro-domains or rafts, as with the cerebrosides. It may also have its own specialized function in the immunological system in that it is known to bind to specific bacteria. In addition, it is believed that a number of pro-inflammatory factors activate lactosylceramide synthase to generate lactosylceramide, which in turn activates "oxygen-sensitive" signalling pathways that affect such cellular processes as proliferation, adhesion, migration and angiogenesis. Dysfunctions in these pathways can affect several diseases of the cardiovascular system, cancer and inflammatory states, so lactosylceramide metabolism is a potential target for new therapeutic treatments. beta-D-Galactosyl-1,4-beta-D-glucosylceramide is the second to last step in the synthesis of N-Acylsphingosine and is converted from Glucosylceramide via the enzyme beta-1,4-galactosyltransferase 6(EC:2.4.1.-). It can be converted to Glucosylceramide via the enzyme beta-galactosidase (EC:3.2.1.23). [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
LacCer(D18:1/24:0)ChEBI
N-(Tetracosanoyl)-1-b-lactosyl-sphing-4-enineChEBI
b-D-Galactosyl-(1->4)-b-D-glucosyl-(11)-N-tetracosanoylsphingosineGenerator, HMDB
β-D-Galactosyl-(1->4)-β-D-glucosyl-(11)-N-tetracosanoylsphingosineGenerator, HMDB
LactosylceramideMetBuilder
N-(Tetracosanoyl)-1-β-lactosyl-sphing-4-enineMetBuilder
Lactosylceramide(d18:1/24:0)MetBuilder
N-(Tetracosanoyl)-1-β-lactosyl-sphingosineMetBuilder
N-(Tetracosanoyl)-1-β-lactosyl-D-erythro-sphingosineMetBuilder
N-(Tetracosanoyl)-1-β-lactosyl-4-sphingenineMetBuilder
N-(Tetracosanoyl)-1-β-lactosyl-D-sphingosineMetBuilder
N-(Tetracosanoyl)-1-β-lactosyl-sphingenineMetBuilder
N-(Tetracosanoyl)-1-β-lactosyl-erythro-4-sphingenineMetBuilder
LacCer d18:1/24:0HMDB
Lactosylceramide (d18:1,C24:0)HMDB
Lactosylceramide (d18:1/24:0)HMDB
N-Lignoceroylsphingosyl lactosideHMDB
Chemical FormulaC54H103NO13
Average Molecular Mass974.395 g/mol
Monoisotopic Mass973.743 g/mol
CAS Registry NumberNot Available
IUPAC NameN-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracosanamide
Traditional NameN-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracosanamide
SMILES[H][C@@](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)(NC(=O)CCCCCCCCCCCCCCCCCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCC
InChI IdentifierInChI=1S/C54H103NO13/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-46(59)55-42(43(58)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2)41-65-53-51(64)49(62)52(45(40-57)67-53)68-54-50(63)48(61)47(60)44(39-56)66-54/h35,37,42-45,47-54,56-58,60-64H,3-34,36,38-41H2,1-2H3,(H,55,59)/b37-35+/t42-,43+,44+,45+,47-,48-,49+,50+,51+,52+,53+,54-/m0/s1
InChI KeyKDEYEEYMIPNKIJ-OGIIFMLESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassGlycosphingolipids
Direct ParentGlycosyl-N-acylsphingosines
Alternative Parents
Substituents
  • Glycosyl-n-acylsphingosine
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty amide
  • N-acyl-amine
  • Oxane
  • Fatty acyl
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-N-acylsphingosine (CHEBI:84764 )
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 Solubility0.0024 g/LALOGPS
logP7.41ALOGPS
logP10.88ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)11.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area227.86 ŲChemAxon
Rotatable Bond Count44ChemAxon
Refractivity267.41 m³·mol⁻¹ChemAxon
Polarizability120.56 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0btc-0102005529-5a7c2cd0cb37ce86e633Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01po-0213209832-0136b0b482b6376feebaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03l3-1719714563-e0bb814c60dfdb529aebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fk9-0312004239-690f4c6a9ff6c6dfaba4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0itc-4705026934-50f237a6f4960e03675cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-4902102020-f37f0974711d18799ab4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-2400009254-418c48c406bc350be9d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qc-3900005301-dcc34f2668b2a28bd4c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02tc-4910005100-89706dc05f3fb692a3e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0101000109-63682271662de10e23c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06rx-7593002325-d7f40628549239745531Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-5329513000-dc8535504008afee0c70Spectrum
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 IDHMDB0011595
FooDB IDFDB028308
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24765753
ChEBI ID84764
PubChem Compound ID53481001
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available