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Showing Compound Lactosylcermide (d18:1/20:0) (FDB028306)

Record Information
Version1.0
Creation date2011-09-21 01:37:39 UTC
Update date2015-07-21 06:59:22 UTC
Primary IDFDB028306
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLactosylcermide (d18:1/20:0)
DescriptionLactosylceramide (d18:1/20:0) 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 NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.0046 g/LALOGPS
logP6.64ALOGPS
logP9.1ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)11.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area227.86 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity249.01 m³·mol⁻¹ChemAxon
Polarizability111.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC50H95NO13
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]icosanamide
InChI IdentifierInChI=1S/C50H95NO13/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-42(55)51-38(39(54)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2)37-61-49-47(60)45(58)48(41(36-53)63-49)64-50-46(59)44(57)43(56)40(35-52)62-50/h31,33,38-41,43-50,52-54,56-60H,3-30,32,34-37H2,1-2H3,(H,51,55)/b33-31+/t38-,39+,40+,41+,43-,44-,45+,46+,47+,48+,49+,50-/m0/s1
InChI KeyFGJIXPPBZNPEHW-CRMMDXJYSA-N
Isomeric 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)CCCCCCCCCCCCCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCC
Average Molecular Weight918.2882
Monoisotopic Molecular Weight917.680342131
Classification
Description Belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-aminopurines
Alternative Parents
Substituents
  • 6-aminopurine
  • Aminopyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Disposition

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Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zg0-0130032928-7752769383ae73c606b82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0140161911-2533e445ce9facf69eb62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03y0-1691731841-9436dcfc457ff307f07c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gi1-1532052978-5226462fdd198982b31c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01w1-3613162940-0d7959f58923d7720b7a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0h00-4901120200-e21f1f6fe4c02cbce38e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0102000229-4248c6f33d014f47a24e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07vu-7593030251-0e3ef15d1857aa17328d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k9f-3239030000-b162809b348dc7344a952021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-1500090704-08ef32e5a25ba27bb30b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-3900050301-217a4cdf524f05b461522021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-3910022000-d04830789a6dacb7c7d72021-09-23View Spectrum
NMRNot Available
ChemSpider ID30776593
ChEMBL IDNot Available
KEGG Compound IDC01290
Pubchem Compound ID53481000
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11593
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
Processing...
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