Showing metabocard for Lactosylceramide (d18:1/16:0) (BMDB0006750)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:25:30 UTC
Update Date2020-05-11 20:41:33 UTC
BMDB IDBMDB0006750
Secondary Accession Numbers
  • BMDB06750
Metabolite Identification
Common NameLactosylceramide (d18:1/16:0)
DescriptionLacCer(d18:1/16:0), also known as beta-D-Galactosyl-1,4-beta-D-glucosylceramide, is a lactosylceramide (LacCer). Lactosylceramides are members of the class of compounds known as sphingolipids (SPs), or glycosylceramides. SPs are lipids containing a backbone of sphingoid bases (e.g. sphingosine or sphinganine) that are often covalently bound to a fatty acid derivative through N-acylation. SPs are found in cell membranes, particularly in peripheral nerve cells and the cells found in the central nervous system (including the brain and spinal cord). Sphingolipids are extremely versatile molecules that have functions controlling fundamental cellular processes such as cell division, differentiation, and cell death. Impairments associated with sphingolipid metabolism are associated with many common human diseases such as diabetes, various cancers, microbial infections, diseases of the cardiovascular and respiratory systems, Alzheimer’s disease and other neurological syndromes. The biosynthesis and catabolism of sphingolipids involves a large number of intermediate metabolites where many different enzymes are involved. Simple sphingolipids, which include the sphingoid bases and ceramides, make up the early products of the sphingolipid synthetic pathways, while complex sphingolipids may be formed by the addition of head groups to the ceramide template (Wikipedia). LacCers are the most important and abundant of the diosylceramides. LacCers were originally called 'cytolipin H'. They are found in small amounts only in animal tissues, but LacCers have a number of significant biological functions and they are of great importance as biosynthetic precursors to most of the neutral oligoglycosylceramides, sulfatides and gangliosides. In animal tissues, biosynthesis of LacCers involves the addition of a second monosaccharides unit (galactose) as a nucleotide derivative to monoglucosylceramide. This is catalysed by a specific beta-1,4-galactosyltransferase on the lumenal side of the Golgi apparatus. The glucosylceramide precursor must first cross from the cytosolic side of the membrane, possibly via the action of a flippase. The LacCer produced can be further glycosylated or transferred to the plasma membrane. LacCers may assist in stabilizing the plasma membrane and activating receptor molecules in special lipid micro-domains or lipid rafts, as with the cerebrosides. LacCers may also have their own specialized function in the immune system in that LacCers are known to bind to specific bacteria. In addition, it is believed that a number of pro-inflammatory factors activate LacCer synthase to generate LacCer, which in turn activates 'oxygen-sensitive' signalling pathways that affect such cellular processes as proliferation, adhesion, migration and angiogenesis. Dysfunctions in these pathways can lead to several diseases of the cardiovascular system, cancer and other inflammatory conditions, so LacCer metabolism is a potential target for new therapeutic treatments. Beta-D-Galactosyl-1,4-beta-D-glucosylceramide is the second to last step in the synthesis of N-acylsphingosines and is converted. from glucosylceramide via the enzyme beta-1,4-galactosyltransferase 6 (EC:2.4.1.-). It can be converted into glucosylceramide via the enzyme beta-galactosidase (EC:3.2.1.23). In terms of its appearance and structure, LacCer(d18:1/16:0) is a colorless solid that consists of an unsaturated 18-carbon sphingoid base with an attached saturated hexadecanoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
LacCer(d18:1/16:0)ChEBI
N-(Hexadecanoyl)-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
Cytopylin HHMDB
D-Galactosyl-1,4-beta-D-glucosylceramideHMDB
Gal-beta1->4GLC-beta1->1'cerHMDB
LacCerHMDB
Lactosyl ceramide (d18:1/16:0)HMDB
Lactosyl-N-acylsphingosineHMDB
LactosylceramideHMDB
N-(Hexadecanoyl)-1-beta-lactosyl-sphing-4-enineHMDB
b-D-Galactosyl-(1->4)-b-D-glucosyl-(11)-N-hexadecanoylsphingosineGenerator, HMDB
β-D-Galactosyl-(1->4)-β-D-glucosyl-(11)-N-hexadecanoylsphingosineGenerator, HMDB
Lactosyl-N-palmitoyl-sphingosineHMDB
N-(Hexadecanoyl)-1-β-lactosyl-sphing-4-enineMetBuilder
Lactosylceramide(d18:1/16:0)MetBuilder
N-(Hexadecanoyl)-1-β-lactosyl-sphingosineMetBuilder
N-(Hexadecanoyl)-1-β-lactosyl-D-erythro-sphingosineMetBuilder
N-(Hexadecanoyl)-1-β-lactosyl-4-sphingenineMetBuilder
N-(Hexadecanoyl)-1-β-lactosyl-D-sphingosineMetBuilder
N-(Hexadecanoyl)-1-β-lactosyl-sphingenineMetBuilder
N-(Hexadecanoyl)-1-β-lactosyl-erythro-4-sphingenineMetBuilder
Chemical FormulaC46H87NO13
Average Molecular Weight862.1819
Monoisotopic Molecular Weight861.617741875
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]hexadecanamide
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]hexadecanamide
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)CCCCCCCCCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C46H87NO13/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-35(50)34(47-38(51)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)33-57-45-43(56)41(54)44(37(32-49)59-45)60-46-42(55)40(53)39(52)36(31-48)58-46/h27,29,34-37,39-46,48-50,52-56H,3-26,28,30-33H2,1-2H3,(H,47,51)/b29-27+/t34-,35+,36+,37+,39-,40-,41+,42+,43+,44+,45+,46-/m0/s1
InChI KeyHLIJNIKSBCIDGO-QKLMXXKVSA-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:84758 )
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
logP5.81ALOGPS
logP7.32ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)11.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area227.86 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity230.6 m³·mol⁻¹ChemAxon
Polarizability103.33 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, Positivesplash10-0gwf-0020037290-21dca1ca5fd13c57f9d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0140259220-32ec01568647af1e8a9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1590725520-ad1444f1d366d916d1a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-0311045190-e794a5691906a48c5dcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fhd-2412229030-6bae8d2533cd960334a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0h00-4910122000-20bac4f86c3c31786972View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0101002090-4b261587f6c949cba576View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-090u-5490031140-beeab0c6c4f152a1f39cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053j-2190100000-c3201464db308f2c1e3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w99-1500092550-ed0029181dab77c82234View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01x0-3900043010-66d92e16856ff8a31054View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ikc-3930132100-ee1522004d9ee686651dView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0006750
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024055
KNApSAcK IDNot Available
Chemspider ID24765743
KEGG Compound IDC01290
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477895
PDB IDNot Available
ChEBI ID84758
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available