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Showing Compound Lactosylceramide (d18:1/12:0) (FDB023465)

Record Information
Version1.0
Creation date2011-09-21 00:30:20 UTC
Update date2017-03-11 23:00:22 UTC
Primary IDFDB023465
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLactosylceramide (d18:1/12:0)
DescriptionLactosylceramide (d18:1/12:0) is a lactosylceramide or LacCer. Lactosylceramides are the most important and abundant of the diosylceramides. Lactosylceramides (LacCer) were originally called 'cytolipin H'. It is found in small amounts only in most animal tissues, but it has a number of significant biological functions and it is of great importance as the biosynthetic precursor of most of the neutral oligoglycosylceramides, sulfatides and gangliosides. In animal tissues, biosynthesis of lactosylceramide involves addition of the second monosaccharides unit (galactose) as its nucleotide derivative to monoglucosylceramide, 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 lactosylceramide produced can be further glycosylated or transferred to the plasma membrane. Lactosylceramide may assist in stabilizing the plasma membrane and activating receptor molecules in the special micro-domains or rafts, as with the cerebrosides. It may also have its own specialized function in the immunological system in that it is known to bind to specific bacteria. In addition, it is believed that a number of pro-inflammatory factors activate lactosylceramide synthase to generate lactosylceramide, which in turn activates "oxygen-sensitive" signalling pathways that affect such cellular processes as proliferation, adhesion, migration and angiogenesis. Dysfunctions in these pathways can affect several diseases of the cardiovascular system, cancer and inflammatory states, so lactosylceramide 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-Acylsphingosine and is converted from Glucosylceramide via the enzyme beta-1,4-galactosyltransferase 6(EC:2.4.1.-). It can be converted to Glucosylceramide via the enzyme beta-galactosidase (EC:3.2.1.23). [HMDB]
CAS Number4682-48-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
Lactosyl ceramide (D18:1/12:0)HMDB
Lactosyl-N-acylsphingosineHMDB
LactosylceramideHMDB
N-(Dodecanoyl)-1-b-lactosyl-sphing-4-enineHMDB
N-(Dodecanoyl)-1-beta-lactosyl-sphing-4-enineHMDB
N-Lignoceryl sphingosyl lactosideHMDB
N-(Dodecanoyl)-1-β-lactosyl-sphing-4-enineMetBuilder
Lactosylceramide(D18:1/12:0)MetBuilder
N-(Dodecanoyl)-1-β-lactosyl-sphingosineMetBuilder
N-(Dodecanoyl)-1-β-lactosyl-D-erythro-sphingosineMetBuilder
N-(Dodecanoyl)-1-β-lactosyl-4-sphingenineMetBuilder
N-(Dodecanoyl)-1-β-lactosyl-D-sphingosineMetBuilder
N-(Dodecanoyl)-1-β-lactosyl-sphingenineMetBuilder
N-(Dodecanoyl)-1-β-lactosyl-erythro-4-sphingenineMetBuilder
LacCer(D18:1/12:0)HMDB
CDw17 antigenHMDB
Gal-beta1->4glc-beta1->1'cerHMDB
LacCer(d18:1/12:0)hmdb
Lactosyl ceramide (d18:1/12:0)hmdb
N-(dodecanoyl)-1-b-lactosyl-sphing-4-eninehmdb
N-(dodecanoyl)-1-beta-lactosyl-sphing-4-eninehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP4.61ALOGPS
logP5.55ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)11.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area227.86 ŲChemAxon
Rotatable Bond Count32ChemAxon
Refractivity212.2 m³·mol⁻¹ChemAxon
Polarizability94.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC42H79NO13
IUPAC nameN-[(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]dodecanamide
InChI IdentifierInChI=1S/C42H79NO13/c1-3-5-7-9-11-13-14-15-16-18-19-21-23-25-31(46)30(43-34(47)26-24-22-20-17-12-10-8-6-4-2)29-53-41-39(52)37(50)40(33(28-45)55-41)56-42-38(51)36(49)35(48)32(27-44)54-42/h23,25,30-33,35-42,44-46,48-52H,3-22,24,26-29H2,1-2H3,(H,43,47)/b25-23+/t30-,31+,32+,33+,35-,36-,37+,38+,39?,40+,41+,42-/m0/s1
InChI KeyKNWHKVBHCLQVFX-QXWNENIHSA-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)CCCCCCCCCCC
Average Molecular Weight806.0756
Monoisotopic Molecular Weight805.555141619
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
Physiological effect

Organoleptic effect:

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLactosylceramide (d18:1/12:0), TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0550-0200309610-f6c301e7c9c570cf4fe72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-0410609200-b7f26710a13afd5225ac2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1920705300-3cd1c8617421be9f03422017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ukl-1512409570-3d65cc4bae36410879922017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-3703519300-898303877ac86d41dfad2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-4900302000-222d0bf59eaa278c1a4a2017-09-01View Spectrum
NMRNot Available
ChemSpider ID16744880
ChEMBL IDNot Available
KEGG Compound IDC01290
Pubchem Compound ID20057304
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04866
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
Enzymes
NameGene NameUniProt ID
Alpha-galactosidase AGLAP06280
Lactase-phlorizin hydrolaseLCTP09848
Beta-galactosidaseGLB1P16278
GlucosylceramidaseGBAP04062
Sialidase-2NEU2Q9Y3R4
Sialidase-4NEU4Q8WWR8
Sialidase-1NEU1Q99519
Acid ceramidaseASAH1Q13510
Putative neutral ceramidase CASAH2CP0C7U2
Alkaline ceramidase 2ACER2Q5QJU3
Neutral ceramidaseASAH2Q9NR71
Alkaline ceramidase 1ACER1Q8TDN7
Ganglioside GM2 activatorGM2AP17900
GalactocerebrosidaseGALCP54803
N-acetylglucosaminyl-phosphatidylinositol de-N-acetylasePIGLQ9Y2B2
Sphingomyelin phosphodiesteraseSMPD1P17405
Ceramide glucosyltransferaseUGCGQ16739
Phosphatidylinositol N-acetylglucosaminyltransferase subunit QPIGQQ9BRB3
Phosphatidylinositol N-acetylglucosaminyltransferase subunit APIGAP37287
Phosphatidylinositol N-acetylglucosaminyltransferase subunit HPIGHQ14442
Phosphatidylinositol N-acetylglucosaminyltransferase subunit PPIGPP57054
Phosphatidylinositol N-acetylglucosaminyltransferase subunit CPIGCQ92535
Collagen type IV alpha-3-binding proteinCOL4A3BPQ9Y5P4
T-cell surface glycoprotein CD1e, membrane-associatedCD1EP15812
Epididymal secretory protein E1NPC2P61916
Ceramide synthase 1CERS1P27544
Antigen-presenting glycoprotein CD1dCD1DP15813
GPI mannosyltransferase 1PIGMQ9H3S5
Phosphatidylinositol-glycan biosynthesis class W proteinPIGWQ7Z7B1
Phosphatidylinositol-glycan biosynthesis class X proteinPIGXQ8TBF5
GPI mannosyltransferase 4PIGZQ86VD9
Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferaseB3GNT5Q9BYG0
Beta-1,3-galactosyltransferase 5B3GALT5Q9Y2C3
GPI mannosyltransferase 3PIGBQ92521
Phosphatidylinositol-glycan biosynthesis class F proteinPIGFQ07326
GPI ethanolamine phosphate transferase 2PIGGQ5H8A4
GPI ethanolamine phosphate transferase 1PIGNO95427
GPI ethanolamine phosphate transferase 3PIGOQ8TEQ8
GPI transamidase component PIG-SPIGSQ96S52
GPI transamidase component PIG-TPIGTQ969N2
Phosphatidylinositol glycan anchor biosynthesis class U proteinPIGUQ9H490
GPI mannosyltransferase 2PIGVQ9NUD9
Phosphatidylinositol N-acetylglucosaminyltransferase subunit YPIGYQ3MUY2
Non-lysosomal glucosylceramidaseGBA2Q9HCG7
GPI-anchor transamidasePIGKQ92643
Beta-1,4 N-acetylgalactosaminyltransferase 1B4GALNT1Q00973
Lactosylceramide 4-alpha-galactosyltransferaseA4GALTQ9NPC4
Beta-hexosaminidase subunit betaHEXBP07686
Beta-hexosaminidase subunit alphaHEXAP06865
Lactosylceramide alpha-2,3-sialyltransferaseST3GAL5Q9UNP4
Pathways
NameSMPDB LinkKEGG Link
Sphingolipid MetabolismSMP00034 map00500
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference