Lactosyceramide (d18:1/18:1(9Z)) (CHEM040358)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 20:34:26 UTC
Update Date2016-11-09 01:22:14 UTC
Accession NumberCHEM040358
Identification
Common NameLactosyceramide (d18:1/18:1(9Z))
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
beta-D-Galactosyl-(1->4)-beta-D-glucosyl-(11)-N-[(9Z)-octadecenoyl]-sphing-4-enineChEBI
beta-D-Galactosyl-(1->4)-beta-D-glucosyl-(11)-N-[(9Z)-octadecenoyl]-sphingosineChEBI
beta-D-Galactosyl-(1->4)-beta-D-glucosyl-(11)-N-oleoylsphing-4-enineChEBI
LacCer(D18:1/18:1(9Z))ChEBI
N-(9Z-Octadecenoyl)-1-beta-lactosyl-sphing-4-enineChEBI
N-(9Z-Octadecenoyl)-1-beta-lactosyl-sphingosineChEBI
b-D-Galactosyl-(1->4)-b-D-glucosyl-(11)-N-[(9Z)-octadecenoyl]-sphing-4-enineGenerator
Β-D-galactosyl-(1->4)-β-D-glucosyl-(11)-N-[(9Z)-octadecenoyl]-sphing-4-enineGenerator
b-D-Galactosyl-(1->4)-b-D-glucosyl-(11)-N-[(9Z)-octadecenoyl]-sphingosineGenerator
Β-D-galactosyl-(1->4)-β-D-glucosyl-(11)-N-[(9Z)-octadecenoyl]-sphingosineGenerator
b-D-Galactosyl-(1->4)-b-D-glucosyl-(11)-N-oleoylsphing-4-enineGenerator
Β-D-galactosyl-(1->4)-β-D-glucosyl-(11)-N-oleoylsphing-4-enineGenerator
N-(9Z-Octadecenoyl)-1-b-lactosyl-sphing-4-enineGenerator
N-(9Z-Octadecenoyl)-1-β-lactosyl-sphing-4-enineGenerator
N-(9Z-Octadecenoyl)-1-b-lactosyl-sphingosineGenerator
N-(9Z-Octadecenoyl)-1-β-lactosyl-sphingosineGenerator
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-delta-Galactopyranosyl-beta-delta-glucopyranosyl)-ceramideHMDB
1-O-(4-O-beta-delta-Galactopyranosyl-beta-glucopyranosyl)ceramideHMDB
1Ylce-O-(4-O-beta-delta-galactopyranosyl-beta-glucopyranosyl)ceramideHMDB
beta-D-Galactosyl-1,4-beta-D-glucosylceramideHMDB
beta-delta-Galactosyl-1,4-beta-delta-glucosramideHMDB
beta-delta-Galactosyl-1,4-beta-delta-glucosylceramideHMDB
CDHHMDB
CDW17 AntigenHMDB
Cytolipin HHMDB
D-Galactosyl-1,4-beta-D-glucosylceramideHMDB
delta-Galactosyl-1,4-beta-delta-glucosylceramideHMDB
Gal-beta1->4GLC-beta1->1'cerHMDB
LacCerHMDB
LacCer(D18:1/18:1)HMDB
Lactosyl ceramide (D18:1/18:1(9Z))HMDB
Lactosyl-N-acylsphingosineHMDB
LactosylceramideHMDB
Lactosylceramide (D18:1/18:1)HMDB
N-(Oleoyl)-1-b-lactosyl-sphing-4-enineHMDB
N-(Oleoyl)-1-beta-lactosyl-sphing-4-enineHMDB
N-Lignoceryl sphingosyl lactosideHMDB
b-D-Galactosyl-(1->4)-b-D-glucosyl-(11)-N-oleoylsphingosineHMDB
Β-D-galactosyl-(1->4)-β-D-glucosyl-(11)-N-oleoylsphingosineHMDB
beta-D-Galactosyl-(1->4)-beta-D-glucosyl-(11)-N-oleoylsphingosineHMDB
Chemical FormulaC48H89NO13
Average Molecular Mass888.219 g/mol
Monoisotopic Mass887.633 g/mol
CAS Registry NumberNot Available
IUPAC Name(9Z)-N-[(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]octadec-9-enamide
Traditional Name(9Z)-N-[(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]octadec-9-enamide
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)CCCCCCC\C=C/CCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCC
InChI IdentifierInChI=1S/C48H89NO13/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/h17-18,29,31,36-39,41-48,50-52,54-58H,3-16,19-28,30,32-35H2,1-2H3,(H,49,53)/b18-17-,31-29+/t36-,37+,38+,39+,41-,42-,43+,44+,45+,46+,47+,48-/m0/s1
InChI KeyYVBUQOZKCCPFCZ-HSVHIEHGSA-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 DescriptorsNot Available
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 Solubility0.0057 g/LALOGPS
logP6.24ALOGPS
logP7.85ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)11.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area227.86 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity240.92 m³·mol⁻¹ChemAxon
Polarizability105.82 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, Positivesplash10-0adi-0120033790-71f3ef58b41c7b419216Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0140251920-2bed52a9da05ddc7f02dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g0-1690721530-823f8c3e54d8af0a9395Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ri-0311031590-d6834701069a888036afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0600-3633153940-fdece24178953f1ad714Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00c0-4920111200-defd723e60d70b12077fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0001000190-59c5ebc5001b558de665Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05mx-4592020320-51e23f5cafe9374e8e68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-6289030000-72efe06143bea41caa00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01rb-2500090840-7d89f7559f706cda3c71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-3800090310-3a152d728f4c4e9ceb67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-090u-3900031000-d19a8ca95def6652c884Spectrum
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 IDHMDB0011592
FooDB IDFDB028305
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24765751
ChEBI ID131557
PubChem Compound ID53480999
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
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15329726