Record Information
Version1.0
Creation date2011-09-21 00:37:58 UTC
Update date2015-07-21 06:57:57 UTC
Primary IDFDB023983
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number81693-22-3
Structure
Thumb
Synonyms
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
Chemical FormulaC25H42N2O19
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight674.603
Monoisotopic Molecular Weight674.238177172
Classification
Description Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • Fatty acyl glycoside
  • N-acyl-alpha-hexosamine
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy aldehyde
  • Fatty acyl
  • Oxane
  • Acetamide
  • Alpha-hydroxyaldehyde
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Aldehyde
  • Primary alcohol
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-Sialyl-N-acetyllactosamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08fr-6232209000-5b7d6c6c816d1b9d8fdaSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_1_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_1_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_1_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_1_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Sialyl-N-acetyllactosamine, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0r7i-2053009000-262ffb7e397c48a776f22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-030r-3169000000-0150ae510e69112040572016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03k9-9484000000-729e2465d486ef55b27c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fu-5451119000-e569cd69c456636776452016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9563101000-7cf7327ae93e0b1b0df22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9772000000-6848a76c652edc45be202016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0040039000-99a801b5f96724398d722021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-5191156000-6691a61fdbd0bd08e7172021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9850100000-a47bfe8ff6f6937967ea2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0000119000-d0e2677b25801bdcaddc2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05o0-0024249000-2000919010f7058b38ce2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fkc-9300001000-5c1c76cdf00b3685174e2021-09-25View Spectrum
NMRNot Available
ChemSpider ID17216382
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID16213476
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06581
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference