Showing metabocard for Lactosylcermide (d18:1/20:0) (BMDB0011593)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:21:25 UTC
Update Date2020-04-22 15:45:30 UTC
BMDB IDBMDB0011593
Secondary Accession Numbers
  • BMDB11593
Metabolite Identification
Common NameLactosylcermide (d18:1/20:0)
DescriptionLactosylcermide (d18:1/20:0), also known as laccer(D18:1/20:0) or C20 lactosyl ceramide, belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. Lactosylcermide (d18:1/20:0) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
LacCer(d18:1/20:0)ChEBI
N-(Eicosanoyl)-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
C20 Lactosyl ceramideHMDB
CDHHMDB
CDW17 AntigenHMDB
Cytolipin HHMDB
D-Galactosyl-1,4-beta-D-glucosylceramideHMDB
D-Galactosyl-1-beta-D-glucosylceramideHMDB
Gal-beta1->4GLC-beta1->1'cerHMDB
LacC,4-beta-D-glucosylceramideHMDB
LacCerHMDB
Lactosyl ceramide (d18:1/20:0)HMDB
Lactosyl-N-acylsphingosineHMDB
LactosylceramideHMDB
N-(Eicosanoyl)-1-beta-lactosyl-sphing-4-enineHMDB
N-(Hexadecanoyl)-1-b-lactosyl-sphing-4-enineHMDB
N-(Hexadecanoyl)-1-beta-lactosyl-sphing-4-enineHMDB
b-D-Galactosyl-(1->4)-b-D-glucosyl-(11)-N-eicosanoylsphingosineGenerator, HMDB
β-D-Galactosyl-(1->4)-β-D-glucosyl-(11)-N-eicosanoylsphingosineGenerator, HMDB
LacCer d18:1/20:0HMDB
Lactosylceramide (d18:1,C20:0)HMDB
Lactosylceramide (d18:1/20:0)HMDB
Lactosylceramide(d18:1/20:0)HMDB
Chemical FormulaC50H95NO13
Average Molecular Weight918.2882
Monoisotopic Molecular Weight917.680342131
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]icosanamide
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]icosanamide
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)CCCCCCCCCCCCCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C50H95NO13/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-42(55)51-38(39(54)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2)37-61-49-47(60)45(58)48(41(36-53)63-49)64-50-46(59)44(57)43(56)40(35-52)62-50/h31,33,38-41,43-50,52-54,56-60H,3-30,32,34-37H2,1-2H3,(H,51,55)/b33-31+/t38-,39+,40+,41+,43-,44-,45+,46+,47+,48+,49+,50-/m0/s1
InChI KeyFGJIXPPBZNPEHW-CRMMDXJYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-aminopurines
Alternative Parents
Substituents
  • 6-aminopurine
  • Aminopyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP6.64ALOGPS
logP9.1ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)11.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area227.86 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity249.01 m³·mol⁻¹ChemAxon
Polarizability111.95 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, Positivesplash10-0zg0-0130032928-7752769383ae73c606b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0140161911-2533e445ce9facf69eb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03y0-1691731841-9436dcfc457ff307f07cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gi1-1532052978-5226462fdd198982b31cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01w1-3613162940-0d7959f58923d7720b7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0h00-4901120200-e21f1f6fe4c02cbce38eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0102000229-4248c6f33d014f47a24eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07vu-7593030251-0e3ef15d1857aa17328dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k9f-3239030000-b162809b348dc7344a95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-1500090704-08ef32e5a25ba27bb30bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-3900050301-217a4cdf524f05b46152View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-3910022000-d04830789a6dacb7c7d7View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011593
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028306
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01290
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481000
PDB IDNot Available
ChEBI ID84761
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available