6'-Sialyllactose (CHEM034747)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:10:51 UTC
Update Date2016-11-09 01:21:11 UTC
Accession NumberCHEM034747
Identification
Common Name6'-Sialyllactose
ClassSmall Molecule
Description6'-Sialyllactose belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. 6'-Sialyllactose is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2>6')-a-sialyllactoseHMDB
(2>6')-alpha-sialyllactoseHMDB
(2>6')-sialyllactoseHMDB
6'-a-SialyllactoseHMDB
6'-alpha-SialyllactoseHMDB
6'-MonosialyllactoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2-3)-O-beta-D-galactopyranosyl-(1-4)-D-glucoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2-3)-O-beta-delta-galactopyranosyl-(1-4)-delta-glucoseHMDB
(2R,4S,5R,6R)-4-Hydroxy-5-[(1-hydroxyethylidene)amino]-2-{[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-2-yl]methoxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateHMDB
6'-SialyllactoseMeSH
Chemical FormulaC23H39NO19
Average Molecular Mass633.551 g/mol
Monoisotopic Mass633.212 g/mol
CAS Registry Number35890-39-2
IUPAC Name(2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-{[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-2-yl]methoxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-{[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-2-yl]methoxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
SMILESCC(=O)NC1C(O)CC(OCC2OC(OC3C(CO)OC(O)C(O)C3O)C(O)C(O)C2O)(OC1C(O)C(O)CO)C(O)=O
InChI IdentifierInChI=1S/C23H39NO19/c1-6(27)24-11-7(28)2-23(22(37)38,43-19(11)12(30)8(29)3-25)39-5-10-13(31)14(32)17(35)21(41-10)42-18-9(4-26)40-20(36)16(34)15(18)33/h7-21,25-26,28-36H,2-5H2,1H3,(H,24,27)(H,37,38)
InChI KeyTYALNJQZQRNQNQ-UHFFFAOYSA-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
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Organopnictogen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • beta-D-Gal-(1->3)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-D-Glc (CHEBI:53481 )
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 Solubility99.5 g/LALOGPS
logP-2.8ALOGPS
logP-7.7ChemAxon
logS-0.8ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area342.92 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity130.03 m³·mol⁻¹ChemAxon
Polarizability58.41 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01b9-9202158000-b439176314d868764595Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-1912068000-d17393334dafaf316409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-4915020000-385305279dc06c3aaa7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9731010000-4f4bfea7ead4ea37990bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-022c-4941064000-38270a81e0872f5d02aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06tr-9834012000-cba3a4d93580b3f5dccaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9621000000-a0a6a1c6d1648d30d616Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053r-2110179000-d87b6bf93bb8407d5ed0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06si-3070292000-8de17e6149de52927b16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-073b06a22652a7d8fb8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0hmt-2700894000-f3241190fd335bd642d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9702210000-02ffe0a958770e124e24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03nc-8935100000-a0569e822448ca14eebbSpectrum
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 IDHMDB0006569
FooDB IDFDB021796
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID559069
ChEBI IDNot Available
PubChem Compound ID643987
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579
2. Pozsgay, Vince; Jennings, Harold J.; Kasper, Dennis L. A novel approach to N-acetylneuraminic acid-containing oligosaccharides. Synthesis of a glycosyl donor derivative of a-N-acetyl-D-neuraminyl-(2 ® 6)-D-galactose. Journal of Carbohydrate Chemistry (1987), 6(1), 41-55.
3. Renlund M, Chester MA, Lundblad A, Aula P, Raivio KO, Autio S, Koskela SL: Increased urinary excretion of free N-acetylneuraminic acid in thirteen patients with Salla disease. Eur J Biochem. 1979 Nov 1;101(1):245-50.
4. Michalski JC, Corfield AP, Schauer R: Properties of human liver lysosomal sialidase. Biol Chem Hoppe Seyler. 1986 Aug;367(8):715-22.
5. Watanabe Y, Shiratsuchi A, Shimizu K, Takizawa T, Nakanishi Y: Stimulation of phagocytosis of influenza virus-infected cells through surface desialylation of macrophages by viral neuraminidase. Microbiol Immunol. 2004;48(11):875-81.
6. Parente F, Cucino C, Anderloni A, Grandinetti G, Bianchi Porro G: Treatment of Helicobacter pylori infection using a novel antiadhesion compound (3'sialyllactose sodium salt). A double blind, placebo-controlled clinical study. Helicobacter. 2003 Aug;8(4):252-6.
7. Ha KT, Lee YC, Cho SH, Kim JK, Kim CH: Molecular characterization of membrane type and ganglioside-specific sialidase (Neu3) expressed in E. coli. Mol Cells. 2004 Apr 30;17(2):267-73.
8. Ng KJ, Andresen BD, Hilty MD, Bianchine JR: Identification of long chain dicarboxylic acids in the serum of two patients with Reye's syndrome. J Chromatogr. 1983 Aug 12;276(1):1-10.
9. Angeloni S, Ridet JL, Kusy N, Gao H, Crevoisier F, Guinchard S, Kochhar S, Sigrist H, Sprenger N: Glycoprofiling with micro-arrays of glycoconjugates and lectins. Glycobiology. 2005 Jan;15(1):31-41. Epub 2004 Sep 1.
10. Burger O, Weiss E, Sharon N, Tabak M, Neeman I, Ofek I: Inhibition of Helicobacter pylori adhesion to human gastric mucus by a high-molecular-weight constituent of cranberry juice. Crit Rev Food Sci Nutr. 2002;42(3 Suppl):279-84.
11. Hanasaki K, Powell LD, Varki A: Binding of human plasma sialoglycoproteins by the B cell-specific lectin CD22. Selective recognition of immunoglobulin M and haptoglobin. J Biol Chem. 1995 Mar 31;270(13):7543-50.
12. Tringali C, Papini N, Fusi P, Croci G, Borsani G, Preti A, Tortora P, Tettamanti G, Venerando B, Monti E: Properties of recombinant human cytosolic sialidase HsNEU2. The enzyme hydrolyzes monomerically dispersed GM1 ganglioside molecules. J Biol Chem. 2004 Jan 30;279(5):3169-79. Epub 2003 Nov 12.
13. Koseki M, Tsurumi K: A convenient method for the isolation of 3'-sialyllactose from normal human urine. J Biochem. 1977 Dec;82(6):1785-8.
14. Serafini-Cessi F, Malagolini N, Dall'Olio F: Characterization and partial purification of beta-N-acetylgalactosaminyltransferase from urine of Sd(a+) individuals. Arch Biochem Biophys. 1988 Nov 1;266(2):573-82.
15. Ding K, Ekberg T, Zeuthen J, Teneberg S, Karlsson KA, Rosen A: Monoclonal antibody against a lactose epitope of glycosphingolipids binds to melanoma tumour cells. Glycoconj J. 1993 Oct;10(5):395-405.