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Record Information
StatusDetected but not Quantified
Creation Date2007-05-28 10:43:19 UTC
Update Date2020-02-26 21:26:38 UTC
Secondary Accession Numbers
  • HMDB06631
Metabolite Identification
Common NameSialyllacto-N-tetraose c
DescriptionSialyllacto-N-tetraose c is a sialylated oligosaccharide normally occurring in human breast milk. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. The acidic oligosaccharides of human milk are predominantly sialyloligosaccharides. Pathogens that bind sialic acid-containing glycans on their host mucosal surfaces may be inhibited by human milk sialyloligosaccharides. Sialyl oligosaccharides of human milk/colostrum are generally believed to be of biological significance, for example providing precursors for biosynthesis of brain. The levels of sialyllacto-N-tetraose are higher on day 3 than on day 1. These results are consistent with the view that during the first 3 d of lactation, the concentration of sialyl oligosaccharides in human colostrum change in accordance with the physiological demands of newborn infants. (PMID: 9426699 , 2318868 ; 10683228, 1778981, 17761135, 17587674).
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-D-galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)- D-glucoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-delta-galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)- D-glucoseHMDB
Chemical FormulaC37H62N2O29
Average Molecular Weight998.8842
Monoisotopic Molecular Weight998.343824032
IUPAC Name2-({6-[(6-{[3,5-dihydroxy-2-(hydroxymethyl)-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-4-yl]oxy}-5-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methoxy)-5-acetamido-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
Traditional Name2-({6-[(6-{[3,5-dihydroxy-2-(hydroxymethyl)-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-4-yl]oxy}-5-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methoxy)-5-acetamido-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
CAS Registry Number155500-52-0
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acylneuraminic acids
Alternative Parents
  • Oligosaccharide
  • N-acylneuraminic acid
  • Neuraminic acid
  • Fatty acyl glycoside
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Beta-hydroxy aldehyde
  • Fatty acyl
  • Pyran
  • Oxane
  • Acetamide
  • Alpha-hydroxyaldehyde
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Primary alcohol
  • Aldehyde
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available


Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility62.6 g/LALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count29ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area510.09 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity205.96 m³·mol⁻¹ChemAxon
Polarizability92.59 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0400040009-67dd67eda04977a96ef8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01sl-4903063104-47887538c3880ad57980Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-8932240003-1701bae6c829e036f293Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0203-4629130007-71827ae78e1094ab35e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-9622220306-e8aa42cc4ca2146a9e89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvi-9734300000-609eb0e286083d90a1d1Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024015
KNApSAcK IDNot Available
Chemspider ID3618994
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4418533
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Coppa GV, Pierani P, Zampini L, Bruni S, Carloni I, Gabrielli O: Characterization of oligosaccharides in milk and feces of breast-fed infants by high-performance anion-exchange chromatography. Adv Exp Med Biol. 2001;501:307-14. [PubMed:11787695 ]
  2. Martin-Sosa S, Martin MJ, Garcia-Pardo LA, Hueso P: Sialyloligosaccharides in human and bovine milk and in infant formulas: variations with the progression of lactation. J Dairy Sci. 2003 Jan;86(1):52-9. [PubMed:12613848 ]
  3. Martin-Sosa S, Martin MJ, Hueso P: The sialylated fraction of milk oligosaccharides is partially responsible for binding to enterotoxigenic and uropathogenic Escherichia coli human strains. J Nutr. 2002 Oct;132(10):3067-72. [PubMed:12368397 ]
  4. Kunz C, Rudloff S, Hintelmann A, Pohlentz G, Egge H: High-pH anion-exchange chromatography with pulsed amperometric detection and molar response factors of human milk oligosaccharides. J Chromatogr B Biomed Appl. 1996 Oct 25;685(2):211-21. [PubMed:8953162 ]
  5. Ravindranath MH, Kelley MC, Jones RC, Amiri AA, Bauer PM, Morton DL: Ratio of IgG:IgM antibodies to sialyl Lewis(x) and GM3 correlates with tumor growth after immunization with melanoma-cell vaccine with different adjuvants in mice. Int J Cancer. 1998 Jan 5;75(1):117-24. [PubMed:9426699 ]
  6. Kitagawa H, Nakada H, Numata Y, Kurosaka A, Fukui S, Funakoshi I, Kawasaki T, Shimada I, Inagaki F, Yamashina I: Occurrence of tetra- and pentasaccharides with the sialyl-Le(a) structure in human milk. J Biol Chem. 1990 Mar 25;265(9):4859-62. [PubMed:2318868 ]