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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:26:32 UTC
HMDB IDHMDB0006569
Secondary Accession Numbers
  • HMDB06569
Metabolite Identification
Common Name6'-Sialyllactose
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 an extremely weak basic (essentially neutral) compound (based on its pKa). Sialyllactose has recently been shown to inhibit the infection of HIV-1 virus. Sialyllactose is also responsible for the inhibitory activity of milk on cholera toxin. Sialyllactose is an oligossaccharide found in both human breast milk and cow's milk. It is the predominant sialylated component in milk.
Structure
Data?1582752392
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-carboxylateGenerator
6'-SialyllactoseMeSH
Chemical FormulaC23H39NO19
Average Molecular Weight633.5511
Monoisotopic Molecular Weight633.211628071
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
CAS Registry Number35890-39-2
SMILES
[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@H]1O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@H](O)[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C23H39NO19/c1-7(28)24-13-8(29)2-23(22(38)39,43-20(13)15(34)10(31)4-26)40-6-12-16(35)17(36)18(37)21(41-12)42-19(11(32)5-27)14(33)9(30)3-25/h3,8-21,26-27,29-37H,2,4-6H2,1H3,(H,24,28)(H,38,39)/t8-,9-,10+,11+,12+,13+,14+,15+,16-,17-,18+,19+,20+,21-,23+/m0/s1
InChI KeyVMWYCXKMRSTDSP-GIGDJUIZSA-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
  • N-acylneuraminic acid
  • Neuraminic acid
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Beta-hydroxy aldehyde
  • Fatty acyl
  • Pyran
  • Oxane
  • Acetamide
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aldehyde
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

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 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Breast Milk
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Breast MilkDetected and Quantified151.5644221+/- 11.1809820 uMAdult (>18 years old)FemaleNormal details
Breast MilkDetected and Quantified119 +/- 54.9 uMAdult (>18 years old)Female
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021796
KNApSAcK IDNot Available
Chemspider ID559069
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound643987
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferencePozsgay, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:510308 ]
  2. Michalski JC, Corfield AP, Schauer R: Properties of human liver lysosomal sialidase. Biol Chem Hoppe Seyler. 1986 Aug;367(8):715-22. [PubMed:3768140 ]
  3. 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. [PubMed:15557745 ]
  4. 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. [PubMed:12950597 ]
  5. 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. [PubMed:15179041 ]
  6. 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. [PubMed:6672002 ]
  7. 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. [PubMed:15342550 ]
  8. 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. [PubMed:12058986 ]
  9. 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. [PubMed:7706301 ]
  10. 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. [PubMed:14613940 ]
  11. 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. [PubMed:599156 ]
  12. 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. [PubMed:3142362 ]
  13. 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. [PubMed:7507746 ]