You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:38 UTC
HMDB IDHMDB0000825
Secondary Accession Numbers
  • HMDB0006626
  • HMDB00825
  • HMDB06626
Metabolite Identification
Common Name3'-Sialyllactose
Description3'-Sialyllactose belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. 3'-Sialyllactose is an extremely weak basic (essentially neutral) compound (based on its pKa). It is the predominant sialylated component in milk. Sialyllactose has recently been shown to inhibit the infection of HIV-1 virus. Sialyllactose is an oligossaccharide found in both human breast milk and cow's milk. Sialyllactose is also responsible for the inhibitory activity of milk on cholera toxin.
Structure
Data?1582752158
Synonyms
ValueSource
(2>3')-a-sialyllactoseHMDB
(2>3')-alpha-sialyllactoseHMDB
3'-(N-Acetyl-a-neuraminosyl)lactoseHMDB
3'-(N-Acetyl-alpha-neuraminosyl)lactoseHMDB
3'-a-SialyllactoseHMDB
3'-alpha-SialyllactoseHMDB
3'-MonosialyllactoseHMDB
3'-N-Acetylneuraminyl-D-lactoseHMDB
3'-N-Acetylneuraminyl-delta-lactoseHMDB
3'-Sialyl-D-lactoseHMDB
3'-Sialyl-delta-lactoseHMDB
32-N-Acetyl-a-neuraminyllactoseHMDB
32-N-Acetyl-alpha-neuraminyllactoseHMDB
a-Neu5ac-(2>3)-b-D-gal-(1>4)-D-GLCHMDB
a2,3-SialyllactoseHMDB
alpha-Neu5ac-(2>3)-beta-D-gal-(1>4)-D-GLCHMDB
alpha-Neu5ac-(2>3)-beta-delta-gal-(1>4)-delta-GLCHMDB
N-AcetylneuraminoyllactoseHMDB
N-Acetylneuraminyl-2-3-galactopyranosyl-1-4-glucopyranoseHMDB
(2S,4S,5R,6R)-2-{[(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}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateHMDB
3'-SialyllactoseMeSH
Chemical FormulaC23H39NO19
Average Molecular Weight633.5511
Monoisotopic Molecular Weight633.211628071
IUPAC Name(2S,4S,5R,6R)-2-{[(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-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2S,4S,5R,6R)-2-{[(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-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry Number35890-38-1
SMILES
[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(O[C@H]1[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]1O)C(O)=O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C23H39NO19/c1-7(29)24-13-8(30)2-23(22(38)39,42-19(13)15(35)10(32)4-26)43-20-16(36)12(6-28)40-21(17(20)37)41-18(11(33)5-27)14(34)9(31)3-25/h3,8-21,26-28,30-37H,2,4-6H2,1H3,(H,24,29)(H,38,39)/t8-,9-,10+,11+,12+,13+,14+,15+,16-,17+,18+,19+,20-,21-,23-/m0/s1
InChI KeyOIZGSVFYNBZVIK-FHHHURIISA-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
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • O-glycosyl compound
  • Glycosyl compound
  • Ketal
  • Beta-hydroxy aldehyde
  • Fatty acyl
  • Oxane
  • Pyran
  • Acetamide
  • Alpha-hydroxyaldehyde
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aldehyde
  • Organic nitrogen compound
  • Primary alcohol
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • 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 Solubility89 g/LALOGPS
logP-2.6ALOGPS
logP-7.7ChemAxon
logS-0.85ALOGPS
pKa (Strongest Acidic)2.84ChemAxon
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
Polarizability58.66 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, Positivesplash10-0329-9200136000-fffce6abd054ee490a92Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0091000000-7e22772e5e2744079301Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0229-0390000000-002eec5ec089f1eb0e5bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00xs-1930000000-89aed3dbc59d2c137408Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02u1-1905068000-8188f1508e1a6fe4b08aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-1619000000-56b3f7f1b9406974b2ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-8953000000-14875e5817ba52578c18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0229-5910085000-1d9e7dc1c1b15e596033Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a73-9647001000-3efe2b78863a5580b526Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9843000000-ba45a1d17f709c61e7b9Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Breast Milk
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Breast MilkDetected and Quantified144 +/- 43.7 uMAdult (>18 years old)Female
Normal
details
Breast MilkDetected and Quantified155.3391290 +/-13.6838556 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleEpithelial ovarian cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021795
KNApSAcK IDNot Available
Chemspider ID110445
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5788
PubChem Compound123914
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceMasuda, Mika; Kawase, Yuuji; Kawase, Mitsuo. Enzymic synthesis of (a2-3) sialyllactose using a membrane reactor. Seibutsu Kogaku Kaishi (2001), 79(9), 345-348.
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]