Sialyl Lea tetra (CHEM036184)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:17:48 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036184
Identification
Common NameSialyl Lea tetra
ClassSmall Molecule
DescriptionSialyl Lea tetra is a sialylated oligosaccharide normally occurring in human breast milk, with N-acetylglucosamine as the reducing-end residue. 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. Sialyl Lewis a is increasingly expressed in melanoma cells, and hypothetically immunotherapy eliciting a humoral response could be therapeutically effective against tumors. (PMID: 9426699, 2318868; 10683228, 1778981).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
NeuAca2->3galb1->3(fuca1->4)glcnacHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)- D-galactoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)- D-galactoseHMDB
(2S,4S,5R)-2-{[(2R,3R,5S,6R)-3,5-dihydroxy-2-{[(2S,3R,5S,6R)-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-2-{[(2R,3S,4S,5R)-2,4,5,6-tetrahydroxy-1-oxohexan-3-yl]oxy}-5-{[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateGenerator, HMDB
Chemical FormulaC37H62N2O28
Average Molecular Mass982.885 g/mol
Monoisotopic Mass982.349 g/mol
CAS Registry Number127321-43-1
IUPAC Name(2S,4S,5R)-5-acetamido-2-{[(2R,3R,5S,6R)-2-{[(2S,3R,5S,6R)-3-acetamido-6-(hydroxymethyl)-2-{[(2R,3S,4S,5R)-2,4,5,6-tetrahydroxy-1-oxohexan-3-yl]oxy}-5-{[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2S,4S,5R)-5-acetamido-2-{[(2R,3R,5S,6R)-2-{[(2S,3R,5S,6R)-3-acetamido-6-(hydroxymethyl)-2-{[(2R,3S,4S,5R)-2,4,5,6-tetrahydroxy-1-oxohexan-3-yl]oxy}-5-{[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
SMILESC[C@@H]1OC(O[C@@H]2[C@@H](CO)O[C@@H](O[C@H]([C@@H](O)C=O)[C@@H](O)[C@H](O)CO)[C@H](NC(C)=O)C2O[C@@H]2O[C@H](CO)[C@H](O)C(O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)C(O3)C(O)[C@H](O)CO)C(O)=O)[C@H]2O)[C@@H](O)[C@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C37H62N2O28/c1-10-21(51)25(55)26(56)34(60-10)64-29-18(9-44)62-33(63-28(16(50)7-42)22(52)14(48)5-40)20(39-12(3)46)31(29)65-35-27(57)32(24(54)17(8-43)61-35)67-37(36(58)59)4-13(47)19(38-11(2)45)30(66-37)23(53)15(49)6-41/h7,10,13-35,40-41,43-44,47-57H,4-6,8-9H2,1-3H3,(H,38,45)(H,39,46)(H,58,59)/t10-,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 KeyARDCDNROJUBBMX-NJMSAGAYSA-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
  • N-acyl-alpha-hexosamine
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • C-glycosyl compound
  • Ketal
  • Fatty acyl
  • Pyran
  • Oxane
  • Acetamide
  • Alpha-hydroxyaldehyde
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Aldehyde
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Organic oxide
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility79.2 g/LALOGPS
logP-2.6ALOGPS
logP-11ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.87ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count28ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area489.86 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity204.41 m³·mol⁻¹ChemAxon
Polarizability92.66 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0101042049-2386bb26b689ceadebaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007o-1201097010-960be680245544466d14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ai-5219183221-b0b3785bbeeefa884af5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0h9c-4630000019-7e005233b30d61a5cdf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bti-9545012114-bb18cfe2fe1ad82b2edeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-8493010000-de6fa864d5415700c8f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-0020000039-b3831e6afeae7fb00351Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03kd-5910000178-e6e6a1bc735668d3e845Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-8005132901-e96a09529f33e5718bf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000089-b59c5393dada41f7b940Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01di-0200006398-c5bc8afeb480d82478c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ac1-9600005022-054ba59bc8acdaf22a70Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006633
FooDB IDFDB024016
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35016015
ChEBI IDNot Available
PubChem Compound ID53477879
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Roth, Steve. Enzymic preparation of oligosaccharides for conjugation to biological macromolecules. PCT Int. Appl. (1991), 50 pp. CODEN: PIXXD2 WO 9116449 A1 19911031 CAN 116:126977 AN 1992:126977
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.
3. 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.