Back to Compounds

Showing Compound LacCer(d18:1/26:1(17Z)) (FDB112390)

Record Information
Version1.0
Creation date2020-04-20 20:20:06 UTC
Update date2020-04-21 18:03:45 UTC
Primary IDFDB112390
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLacCer(d18:1/26:1(17Z))
DescriptionLacCer(d18:1/26:1(17Z)), 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(d18:1/26:1(17Z)) is a colorless solid that consists of an unsaturated 18-carbon sphingoid base with an attached unsaturated 17Z-hexacosenoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481).
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(17Z)-N-[(2S,3R,4E)-1-{[(2R,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]hexacos-17-enimidateHMDB
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-glucoceramideHMDB
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
Lactosyl ceramide (D18:1/26:1(17Z))HMDB
Lactosyl-N-acylsphingosineHMDB
LactosylceramideHMDB
N-Lignoceryl sphingosyl lactosideHMDB
N-(17Z-Hexacosenoyl)-1-β-lactosyl-sphing-4-enineMetBuilder
Lactosylceramide(D18:1/26:1(17Z))MetBuilder
N-(17Z-Hexacosenoyl)-1-β-lactosyl-sphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-β-lactosyl-D-erythro-sphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-β-lactosyl-4-sphingenineMetBuilder
N-(17Z-Hexacosenoyl)-1-β-lactosyl-D-sphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-β-lactosyl-sphingenineMetBuilder
N-(17Z-Hexacosenoyl)-1-β-lactosyl-erythro-4-sphingenineMetBuilder
LacCer(D18:1/26:1(17Z))HMDB
Predicted Properties
PropertyValueSource
Water Solubility0.0019 g/LALOGPS
logP7.7ALOGPS
logP11.41ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)11.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area227.86 ŲChemAxon
Rotatable Bond Count45ChemAxon
Refractivity277.73 m³·mol⁻¹ChemAxon
Polarizability123.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC56H105NO13
IUPAC name(17Z)-N-[(2S,3R,4E)-1-{[(2R,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]hexacos-17-enamide
InChI IdentifierInChI=1S/C56H105NO13/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-48(61)57-44(45(60)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2)43-67-55-53(66)51(64)54(47(42-59)69-55)70-56-52(65)50(63)49(62)46(41-58)68-56/h17-18,37,39,44-47,49-56,58-60,62-66H,3-16,19-36,38,40-43H2,1-2H3,(H,57,61)/b18-17-,39-37+/t44-,45+,46+,47+,49-,50-,51+,52+,53?,54+,55+,56-/m0/s1
InChI KeyZUFRMROYCSRBIP-HUMXCGMZSA-N
Isomeric SMILESCCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](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)C1O)NC(=O)CCCCCCCCCCCCCCC\C=C/CCCCCCCC
Average Molecular Weight1000.4318
Monoisotopic Molecular Weight999.758592451
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference