Lactosylceramide (d18:1/22:0) (CHEM040360)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 20:34:33 UTC
Update Date2016-11-09 01:22:14 UTC
Accession NumberCHEM040360
Identification
Common NameLactosylceramide (d18:1/22:0)
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
β-LacCerChEBI
CDHHMDB
LacCer d18:1/22:0HMDB
LacCer(d18:1/22:0)HMDB
LactosylceramideHMDB
Lactosylceramide (d18:1,C22:0)HMDB
Lactosylceramide (d18:1/22:0)HMDB
Lactosylceramide(d18:1/22:0)HMDB
N-(Docosanoyl)-1-beta-lactosyl-4-sphingenineHMDB
N-(Docosanoyl)-1-beta-lactosyl-D-erythro-sphingosineHMDB
N-(Docosanoyl)-1-beta-lactosyl-D-sphingosineHMDB
N-(Docosanoyl)-1-beta-lactosyl-erythro-4-sphingenineHMDB
N-(Docosanoyl)-1-beta-lactosyl-sphing-4-enineHMDB
N-(Docosanoyl)-1-beta-lactosyl-sphingenineHMDB
N-(Docosanoyl)-1-beta-lactosyl-sphingosineHMDB
N-(Docosanoyl)-1-β-lactosyl-4-sphingenineHMDB
N-(Docosanoyl)-1-β-lactosyl-D-erythro-sphingosineHMDB
N-(Docosanoyl)-1-β-lactosyl-D-sphingosineHMDB
N-(Docosanoyl)-1-β-lactosyl-erythro-4-sphingenineHMDB
N-(Docosanoyl)-1-β-lactosyl-sphing-4-enineHMDB
N-(Docosanoyl)-1-β-lactosyl-sphingenineHMDB
N-(Docosanoyl)-1-β-lactosyl-sphingosineHMDB
N-[(2S,3R,4E)-1-{[4-O-(b-D-galactopyranosyl)-b-D-glucopyranosyl]oxy}-3-hydroxyoctadec-4-en-2-yl]docosanamideHMDB
N-[(2S,3R,4E)-1-{[4-O-(beta-D-galactopyranosyl)-beta-D-glucopyranosyl]oxy}-3-hydroxyoctadec-4-en-2-yl]docosanamideHMDB
N-[(2S,3R,4E)-1-{[4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl]oxy}-3-hydroxyoctadec-4-en-2-yl]docosanamideHMDB
b-D-Galactosyl-(1->4)-b-D-glucosyl-N-(docosanoyl)sphingosineHMDB
b-LacCerHMDB
b-Lactosyl-N-(docosanoyl)sphingosineHMDB
b-LactosylceramideHMDB
beta-D-Galactosyl-(1->4)-beta-D-glucosyl-N-(docosanoyl)sphingosineHMDB
beta-LacCerHMDB
beta-Lactosyl-N-(docosanoyl)sphingosineHMDB
beta-LactosylceramideHMDB
β-D-Galactosyl-(1->4)-β-D-glucosyl-N-(docosanoyl)sphingosineHMDB
β-Lactosyl-N-(docosanoyl)sphingosineHMDB
β-LactosylceramideHMDB
Chemical FormulaC52H99NO13
Average Molecular Mass946.341 g/mol
Monoisotopic Mass945.712 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]docosanamide
Traditional NameCDH
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)CCCCCCCCCCCCCCCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCC
InChI IdentifierInChI=1S/C52H99NO13/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-44(57)53-40(41(56)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2)39-63-51-49(62)47(60)50(43(38-55)65-51)66-52-48(61)46(59)45(58)42(37-54)64-52/h33,35,40-43,45-52,54-56,58-62H,3-32,34,36-39H2,1-2H3,(H,53,57)/b35-33+/t40-,41+,42+,43+,45-,46-,47+,48+,49+,50+,51+,52-/m0/s1
InChI KeyQYWVASPEUXEHSY-NNRNTGNWSA-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:62109 )
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 Solubility0.0032 g/LALOGPS
logP7.05ALOGPS
logP9.99ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)11.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area227.86 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity258.21 m³·mol⁻¹ChemAxon
Polarizability116.28 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, Positivesplash10-00or-0111004809-3d472fd9629198430f93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0222116912-c8f59a495e4350a4c0ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-1774914752-d7bcdacf6bb987f798e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-0312004419-e066b9667abc0b46f46fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-3504043903-eef9aa9b4e5171faba55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-4902111200-70ea0c13127e2b5893e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0feb-2500018905-a33e29571335a1877ac8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxs-3900013301-bdf42a957cb2cb56277cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01vx-4910021100-8244f0288c2d525ca600Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0101000109-77350ecf3f81c1ee5cb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06r6-7593003234-65c1a3db4ccd6c3d034eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06z9-3219020000-0d5f3fd1908f635e3896Spectrum
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 IDHMDB0011594
FooDB IDFDB028307
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 ID62109
PubChem Compound ID52921641
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
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15727820