Showing metabocard for Lactosylceramide (d18:1/22:0) (BMDB0011594)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:21:26 UTC
Update Date2020-04-22 15:45:30 UTC
BMDB IDBMDB0011594
Secondary Accession Numbers
  • BMDB11594
Metabolite Identification
Common NameLactosylceramide (d18:1/22:0)
DescriptionLacCer(d18:1/22:0), 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(d18:1/22:0) is a colorless solid that consists of an unsaturated 18-carbon sphingoid base with an attached saturated docosanoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481 ).
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 Weight946.3414
Monoisotopic Molecular Weight945.711642259
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
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)CCCCCCCCCCCCCCCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=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 )
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
logP7.05ALOGPS
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
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, Positivesplash10-00or-0111004809-3d472fd9629198430f93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0222116912-c8f59a495e4350a4c0ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-1774914752-d7bcdacf6bb987f798e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-0312004419-e066b9667abc0b46f46fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-3504043903-eef9aa9b4e5171faba55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-4902111200-70ea0c13127e2b5893e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0feb-2500018905-a33e29571335a1877ac8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxs-3900013301-bdf42a957cb2cb56277cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01vx-4910021100-8244f0288c2d525ca600View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0101000109-77350ecf3f81c1ee5cb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06r6-7593003234-65c1a3db4ccd6c3d034eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06z9-3219020000-0d5f3fd1908f635e3896View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011594
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028307
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52921641
PDB IDNot Available
ChEBI ID62109
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available