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Record Information
Version3.6
Creation Date2007-05-25 09:44:33 UTC
Update Date2017-03-02 21:28:14 UTC
HMDB IDHMDB06607
Secondary Accession NumbersNone
Metabolite Identification
Common Name3'-Sialyllactosamine
Description

3'-Sialyllactosamine is an oligosaccharide found in human milk. Oligosaccharides in human milk inhibit enteric pathogens in vitro and in vivo. (PMID:10683228 )

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Helicobacter pylori-induced activation of neutrophils occurs by lectinophagocytosis, the recognition of sialylated glycoconjugates (3'-sialyllactosamine was the most efficient inhibitor) on the neutrophil cell surface by a bacterial adhesin leads to phagocytosis and an oxidative burst with the production of reactive oxygen metabolites. (PMID: 11087709 )

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Structure
Thumb
Synonyms
ValueSource
3'-SLNHMDB
3-SialyllactosamineHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-2-amino-2-deoxy- D-glucoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->4)-2-amino-2-deoxy- D-glucoseHMDB
Chemical FormulaC23H40N2O18
Average Molecular Weight632.5663
Monoisotopic Molecular Weight632.227612486
IUPAC Name(2S,4S,5R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-5-amino-1,2,4-trihydroxy-6-oxohexan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2S,4S,5R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-5-amino-1,2,4-trihydroxy-6-oxohexan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry Number126151-66-4
SMILES
CC(=O)N[C@@H]1[C@@H](O)C[C@@](O[C@H]2[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](N)C=O)[C@@H]2O)(OC1[C@H](O)[C@H](O)CO)C(O)=O
InChI Identifier
InChI=1S/C23H40N2O18/c1-7(30)25-13-9(31)2-23(22(38)39,42-19(13)15(35)10(32)4-27)43-20-16(36)12(6-29)40-21(17(20)37)41-18(11(33)5-28)14(34)8(24)3-26/h3,8-21,27-29,31-37H,2,4-6,24H2,1H3,(H,25,30)(H,38,39)/t8-,9-,10+,11+,12+,13+,14+,15+,16-,17+,18+,19?,20-,21-,23-/m0/s1
InChI KeyMKNNYTWMAUAKMA-FRLIKFETSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentN-acylneuraminic acids
Alternative Parents
Substituents
  • N-acylneuraminic acid
  • Neuraminic acid
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Amino saccharide
  • Fatty acyl
  • Beta-hydroxy aldehyde
  • Monosaccharide
  • Pyran
  • Oxane
  • Acetamide
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxide
  • Aldehyde
  • Carbonyl group
  • Organopnictogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Amine
  • Primary aliphatic amine
  • Primary amine
  • Organonitrogen compound
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility79.6 mg/mLALOGPS
logP-3ALOGPS
logP-10ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)7.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area348.71 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity131.69 m3·mol-1ChemAxon
Polarizability58.98 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB024000
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06607
Metagene LinkHMDB06607
METLIN IDNot Available
PubChem Compound53477870
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shen Z, Warren CD, Newburg DS: High-performance capillary electrophoresis of sialylated oligosaccharides of human milk. Anal Biochem. 2000 Mar 1;279(1):37-45. [10683228 ]
  2. Teneberg S, Jurstrand M, Karlsson KA, Danielsson D: Inhibition of nonopsonic Helicobacter pylori-induced activation of human neutrophils by sialylated oligosaccharides. Glycobiology. 2000 Nov;10(11):1171-81. [11087709 ]