Lactosylceramide (d18:1/18:0) (CHEM040357)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 20:34:23 UTC
Update Date2016-11-09 01:22:14 UTC
Accession NumberCHEM040357
Identification
Common NameLactosylceramide (d18:1/18:0)
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
LacCer(d18:1/18:0)ChEBI
N-(Octadecanoyl)-1-b-lactosyl-sphing-4-enineChEBI
1-O-(4-O-b-D-Galactopyranosyl-b-D-glucopyranosyl)-ceramideHMDB
1-O-(4-O-beta-D-Galactopyranosyl-beta-glucopyranosyl)ceramideHMDB
1-O-(4-O-beta-D-Galactopyranosyl-beta-D-glucopyranosyl)-ceramideHMDB
beta-D-Galactosyl-1,4-beta-D-glucosylceramideHMDB
beta-D-Galactosyl-1,4-beta-D-glucosramideHMDB
CDHHMDB
CDW17 AntigenHMDB
Cytolipin HHMDB
D-Galactosyl-1,4-beta-D-glucosylceramideHMDB
Gal-beta1->4GLC-beta1->1'cerHMDB
LacCerHMDB
Lactosyl ceramide (d18:1/18:0)HMDB
Lactosyl-N-acylsphingosineHMDB
LactosylceramideHMDB
N-(Octadecanoyl)-1-beta-lactosyl-sphing-4-enineHMDB
b-D-Galactosyl-(1->4)-b-D-glucosyl-(11)-N-octadecanoylsphingosineGenerator, HMDB
β-D-Galactosyl-(1->4)-β-D-glucosyl-(11)-N-octadecanoylsphingosineGenerator, HMDB
N-(Octadecanoyl)-1-β-lactosyl-sphing-4-enineMetBuilder
Lactosylceramide(d18:1/18:0)MetBuilder
N-(Octadecanoyl)-1-β-lactosyl-sphingosineMetBuilder
N-(Octadecanoyl)-1-β-lactosyl-D-erythro-sphingosineMetBuilder
N-(Octadecanoyl)-1-β-lactosyl-4-sphingenineMetBuilder
N-(Octadecanoyl)-1-β-lactosyl-D-sphingosineMetBuilder
N-(Octadecanoyl)-1-β-lactosyl-sphingenineMetBuilder
N-(Octadecanoyl)-1-β-lactosyl-erythro-4-sphingenineMetBuilder
LacCer d18:1/18:0HMDB
Lactosylceramide (d18:1,C18:0)HMDB
Lactosylceramide (d18:1/18:0)HMDB
Chemical FormulaC48H91NO13
Average Molecular Mass890.235 g/mol
Monoisotopic Mass889.649 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]octadecanamide
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]octadecanamide
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)CCCCCCCCCCCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCC
InChI IdentifierInChI=1S/C48H91NO13/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(53)49-36(37(52)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)35-59-47-45(58)43(56)46(39(34-51)61-47)62-48-44(57)42(55)41(54)38(33-50)60-48/h29,31,36-39,41-48,50-52,54-58H,3-28,30,32-35H2,1-2H3,(H,49,53)/b31-29+/t36-,37+,38+,39+,41-,42-,43+,44+,45+,46+,47+,48-/m0/s1
InChI KeyVOZHMDQUIRUFQW-LOTHNZFDSA-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:84759 )
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 Solubility0.0071 g/LALOGPS
logP6.26ALOGPS
logP8.21ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)11.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area227.86 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity239.8 m³·mol⁻¹ChemAxon
Polarizability107.71 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, Positivesplash10-0229-0020033790-a1ea70d98115f6b7a6aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0140251920-cb0673e40deecb4beb82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1590721840-a2036fa87a2a48ab1793Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-009i-0311031590-a5fbd158e42a2641bdedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05i0-3633153940-15f841d270339a3ac075Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4920111200-156187cf0861ed3c2d10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02be-1500090740-b5c477745ebca309ff84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-2900040310-68d6f06cac7ef6dadb55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03yl-3920033000-08b297acd107dcb21c53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0101000190-6f15e791a7a077066a6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ap0-6493030260-26758d0ce90bb5eb495aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-4359030000-3ae1040d8dac6ef44c45Spectrum
MSMass Spectrum (Electron Ionization)Not AvailableSpectrum
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 IDHMDB0011591
FooDB IDFDB028304
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8435601
ChEBI ID84759
PubChem Compound ID10260120
Kegg Compound IDC01290
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