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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2007-05-24 12:38:02 UTC
Update Date2020-02-26 21:26:33 UTC
HMDB IDHMDB0006581
Secondary Accession Numbers
  • HMDB06581
Metabolite Identification
Common Name3-Sialyl-N-acetyllactosamine
Description3-Sialyl-N-acetyllactosamine is a normal sialyloligosaccharide that is present in human biofluids, and is one of the predominant oligosaccharides in human urine as a free form. The presence of these compounds in the urine is linked to the biosynthesis and degradation of the body glycoproteins, glycolipids, and glycans. Under certain pathological conditions, the total urinary carbohydrate-material is increased dramatically, and the number and ratios of the components present are also increased. Many of these pathological disorders are the result of a deficiency in a specific exoglycosidase. 3-Sialyl-N-acetyllactosamine have a sialyl(a2-3) linkage and is of interest in view of the discovery of uropathogenic Escherichia coli strains with binding specificity for sialyl(a2-3)galactosides. (PMID: 2445744 ; 2775488; 3813552; 6619126; 6628386; 6628680; 6714239; 6746638; 7925342).
Structure
Data?1582752393
Synonyms
ValueSource
NeuAc(a2-3)gal(b1-4)glcnacHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-D-glucoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-delta-glucoseHMDB
(2R,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-4,5-dihydroxy-6-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateGenerator
Chemical FormulaC25H42N2O19
Average Molecular Weight674.603
Monoisotopic Molecular Weight674.238177172
IUPAC Name(2R,4S,5R,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-6-acetamido-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2R,4S,5R,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-6-acetamido-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry Number81693-22-3
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]2[C@H](O)[C@@H](O)C(NC(C)=O)O[C@@H]2CO)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C25H42N2O19/c1-7(31)26-13-9(33)3-25(24(40)41,45-20(13)14(35)10(34)4-28)46-21-15(36)11(5-29)43-23(18(21)39)44-19-12(6-30)42-22(27-8(2)32)17(38)16(19)37/h9-23,28-30,33-39H,3-6H2,1-2H3,(H,26,31)(H,27,32)(H,40,41)/t9-,10+,11+,12+,13+,14+,15-,16+,17+,18+,19+,20+,21-,22?,23-,25+/m0/s1
InChI KeyHUNVSYPDCXFGLB-KROWHOKKSA-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
  • C-glucuronide
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Pyran
  • Oxane
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Primary alcohol
  • Organonitrogen compound
  • Organic oxide
  • 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 Solubility66.1 g/LALOGPS
logP-2.7ALOGPS
logP-7.4ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)2.84ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area343.95 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity139.71 m³·mol⁻¹ChemAxon
Polarizability63.55 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-6232209000-5b7d6c6c816d1b9d8fdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0r7i-2053009000-262ffb7e397c48a776f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-030r-3169000000-0150ae510e6911204057Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03k9-9484000000-729e2465d486ef55b27cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fu-5451119000-e569cd69c45663677645Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9563101000-7cf7327ae93e0b1b0df2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9772000000-6848a76c652edc45be20Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>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 IDFDB023983
KNApSAcK IDNot Available
Chemspider ID17216382
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16213476
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceScudder, Peter R.; Shailubhai, Kunwar; Duffin, Kevin L.; Streeter, Philip R.; Jacob, Gary S. Enzymic synthesis of a 6'-sulfated sialyl-Lewisx which is an inhibitor of L-selectin binding to peripheral addressin. Glycobiology (1994), 4(6), 929-32.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Edge AS, Spiro RG: Presence of an O-glycosidically linked hexasaccharide in fetuin. J Biol Chem. 1987 Nov 25;262(33):16135-41. [PubMed:2445744 ]