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
Description
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 IDNot Available
ChEBI ID84764
PubChem Compound ID53481001
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78.
2. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50.
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. Phospholipids Handbook
8. The lipid handbook with CD-ROM