Showing metabocard for Lactosylceramide (d18:1/24:0) (BMDB0011595)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:21:27 UTC
Update Date2020-04-22 15:45:31 UTC
BMDB IDBMDB0011595
Secondary Accession Numbers
  • BMDB11595
Metabolite Identification
Common NameLactosylceramide (d18:1/24:0)
DescriptionLactosylceramide (d18:1/24:0), also known as laccer(D18:1/24:0), 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. Thus, lactosylceramide (D18:1/24:0) is considered to be a neutral glycosphingolipid. Based on a literature review very few articles have been published on Lactosylceramide (d18:1/24:0).
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 Weight974.3945
Monoisotopic Molecular Weight973.742942387
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
CAS Registry NumberNot Available
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 Identifier
InChI=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 )
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Endosome
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0btc-0102005529-5a7c2cd0cb37ce86e633View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01po-0213209832-0136b0b482b6376feebaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03l3-1719714563-e0bb814c60dfdb529aebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fk9-0312004239-690f4c6a9ff6c6dfaba4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0itc-4705026934-50f237a6f4960e03675cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-4902102020-f37f0974711d18799ab4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-2400009254-418c48c406bc350be9d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qc-3900005301-dcc34f2668b2a28bd4c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02tc-4910005100-89706dc05f3fb692a3e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0101000109-63682271662de10e23c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06rx-7593002325-d7f40628549239745531View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-5329513000-dc8535504008afee0c70View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011595
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028308
KNApSAcK IDNot Available
Chemspider ID24765753
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481001
PDB IDNot Available
ChEBI ID84764
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available