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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-05-25 08:39:55 UTC
Update Date2020-02-26 21:26:35 UTC
HMDB IDHMDB0006600
Secondary Accession Numbers
  • HMDB06600
Metabolite Identification
Common NameSialyllacto-N-tetraose b
DescriptionSialyllacto-N-tetraose b 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 ).
Structure
Data?1582752395
Synonyms
ValueSource
LS-Tetrasaccharide bHMDB
LSTBHMDB
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
(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-3-hydroxy-5-[(1-hydroxyethylidene)amino]-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateGenerator
Chemical FormulaC37H62N2O29
Average Molecular Weight998.8842
Monoisotopic Molecular Weight998.343824032
IUPAC Name(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-3-hydroxy-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-3-hydroxy-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry Number64003-54-9
SMILES
CC(=O)N[C@@H]1[C@@H](O)C[C@@](OC[C@H]2O[C@@H](O[C@H]3[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]3O)[C@H](NC(C)=O)[C@@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H]2O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O
InChI Identifier
InChI=1S/C37H62N2O29/c1-10(45)38-19-12(47)3-37(36(59)60,68-31(19)22(52)14(49)5-41)61-9-18-25(55)30(66-34-27(57)26(56)23(53)16(7-43)62-34)20(39-11(2)46)33(64-18)67-32-24(54)17(8-44)63-35(28(32)58)65-29(15(50)6-42)21(51)13(48)4-40/h4,12-35,41-44,47-58H,3,5-9H2,1-2H3,(H,38,45)(H,39,46)(H,59,60)/t12-,13-,14+,15+,16+,17+,18+,19+,20+,21+,22+,23-,24-,25+,26-,27+,28+,29+,30+,31+,32-,33-,34-,35-,37+/m0/s1
InChI KeySFMRPVLZMVJKGZ-JRZQLMJNSA-N
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
Substituents
  • 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
Ontology
Disposition

Biological location:

Source:

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 Solubility74.1 g/LALOGPS
logP-3.2ALOGPS
logP-12ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.86ChemAxon
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
Polarizability94.87 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0400000049-979d3487e4d8a30e01d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02al-3902043144-b611e89ecda7f2d45a72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-9810021235-acda66faf61a04af2996Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05du-3512000019-3cacea2d1164023fdb24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-9722102416-1c718ef0cd4363f278efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvi-9844200000-b65a193acf80f49912ecSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Breast Milk
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Breast MilkDetected and Quantified125.3958078+/-8.5199242 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023994
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477864
PDB IDNot Available
ChEBI ID88450
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceYamashita, Katsuko; Tachibana, Yoko; Kobata, Akira. Oligosaccharides of human milk: structures of three lacto-N-hexaose derivatives with H-haptenic structure. Archives of Biochemistry and Biophysics (1977), 182(2), 546-55.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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. [PubMed:10683228 ]
  4. Kitagawa H, Takaoka M, Nakada H, Fukui S, Funakoshi I, Kawasaki T, Tate S, Inagaki F, Yamashina I: Isolation and structural studies of human milk oligosaccharides that are reactive with a monoclonal antibody MSW 113. J Biochem. 1991 Oct;110(4):598-604. [PubMed:1778981 ]
  5. Bao Y, Zhu L, Newburg DS: Simultaneous quantification of sialyloligosaccharides from human milk by capillary electrophoresis. Anal Biochem. 2007 Nov 15;370(2):206-14. Epub 2007 Jul 7. [PubMed:17761135 ]
  6. Asakuma S, Akahori M, Kimura K, Watanabe Y, Nakamura T, Tsunemi M, Arai I, Sanai Y, Urashima T: Sialyl oligosaccharides of human colostrum: changes in concentration during the first three days of lactation. Biosci Biotechnol Biochem. 2007 Jun;71(6):1447-51. [PubMed:17587674 ]