Lex-lactose (CHEM036195)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:18:37 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036195
Identification
Common NameLex-lactose
ClassSmall Molecule
DescriptionLacto-N-fucopentaose III (LNFPIII) is a polylactosamine sugar, predominant carbohydrate found in S. mansoni egg Ag. Lewis type carbohydrate LNFPIII can function as an adjuvant by their ability to induce a Th2 response (PMID:11418681). LNFPIII/LeX is also expressed by immunosuppressive helminth parasites, by bacteria, and on a number of tumor/cancer cells. According to Atochina et al., LNFPIII-stimulated macrophages secrete prostaglandin E(2), interleukin-10 (IL-10), and tumor necrosis factor alpha (TNF-alpha) but a very low level of IL-12. Interestingly, addition of anti-TNF-alpha, anti-IL-10, or anti-IL-12 monoclonal antibodies did not significantly alter NK cell activity. It shows that soluble mediators are not critical for LNFPIII-stimulated macrophage activation of NK cells and provide further evidence for the importance of cell-cell contact and CD40-CD40L interactions between macrophages and NK cells. (PMID:16148169).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
beta-D-Gal-(1->4)-[alpha-L-fuc-(1->3)]-beta-D-glcnac-(1->3)-beta-D-gal-(1->4)-D-GLCHMDB
lacto-N-Fucopentaose- IIIHMDB
Lewis-X pentasaccharideHMDB
LNFP IIIHMDB
O-6-Deoxy-alpha-D-galactopyranosyl-(1->3)-O-[beta-D-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)- D-glucoseHMDB
O-6-Deoxy-alpha-delta-galactopyranosyl-(1->3)-O-[beta-delta-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)- D-glucoseHMDB
N-[(2S,4R,6R)-2-{[(4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)-5-{[(2S,3R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]ethanimidateGenerator, HMDB
Chemical FormulaC32H55NO25
Average Molecular Mass853.771 g/mol
Monoisotopic Mass853.306 g/mol
CAS Registry Number213250-53-4
IUPAC NameN-[(2S,4R,6R)-2-{[(4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)-5-{[(2S,3R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide
Traditional NameN-[(2S,4R,6R)-2-{[(4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)-5-{[(2S,3R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide
SMILESC[C@H]1O[C@H](O[C@@H]2C(NC(C)=O)[C@H](O[C@H]3C(O)C(CO)O[C@@H](OC(C(O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]3O)O[C@H](CO)C2O[C@@H]2OC(CO)C(O)C(O)[C@H]2O)C(O)[C@@H](O)[C@H]1O
InChI IdentifierInChI=1S/C32H55NO25/c1-8-16(42)20(46)22(48)30(51-8)57-27-15(33-9(2)39)29(54-14(7-38)26(27)56-31-23(49)21(47)18(44)12(5-36)52-31)58-28-19(45)13(6-37)53-32(24(28)50)55-25(11(41)4-35)17(43)10(40)3-34/h3,8,10-32,35-38,40-50H,4-7H2,1-2H3,(H,33,39)/t8-,10+,11?,12?,13?,14-,15?,16+,17-,18?,19?,20+,21?,22?,23-,24-,25?,26?,27-,28+,29+,30-,31+,32+/m1/s1
InChI KeyWMYQZGAEYLPOSX-JOEMMLBASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • Fatty acyl glycoside
  • N-acyl-alpha-hexosamine
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy aldehyde
  • Fatty acyl
  • Oxane
  • Acetamide
  • Alpha-hydroxyaldehyde
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Aldehyde
  • Primary alcohol
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility106 g/LALOGPS
logP-2.2ALOGPS
logP-9.9ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)11.41ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area423.46 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity176.56 m³·mol⁻¹ChemAxon
Polarizability79.87 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-007x-0701019150-3553715bda817d3eddd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01po-3902047100-e2565817433522d7241dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01po-5900077210-2403bd1c2954a4e63a6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f83-9444005680-08b3c248934eea6219c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05d0-8606039180-bb9980f5a259848d178cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-6934200000-5f5327ab25733ef950ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00y3-0200029060-3d7670c306de437e5eaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01oy-5400095140-b2cf8d7b3c2b6c9e61b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9700012200-a55f87530c36576f757eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3200001690-9300eed6b28d26477cefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053u-5210005940-8ead92f99b13e61be2e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100011100-60d4dc9d8d6f1bcfc2a2Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006696
FooDB IDFDB024029
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17216408
ChEBI IDNot Available
PubChem Compound ID22833681
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Okano M, Satoskar AR, Nishizaki K, Harn DA Jr: Lacto-N-fucopentaose III found on Schistosoma mansoni egg antigens functions as adjuvant for proteins by inducing Th2-type response. J Immunol. 2001 Jul 1;167(1):442-50.
2. Atochina O, Harn D: LNFPIII/LeX-stimulated macrophages activate natural killer cells via CD40-CD40L interaction. Clin Diagn Lab Immunol. 2005 Sep;12(9):1041-9.