O-beta-D-Gal-(1->3)-O-[O-beta-D-Gal-(1->4)-2-(acetylamino)-2-deoxy-beta-D-Glc-(1->6)]-2-(acetylamino)-2-deoxy-D-Gal (CHEM035319)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:39:31 UTC
Update Date2016-11-09 01:21:17 UTC
Accession NumberCHEM035319
Identification
Common NameO-beta-D-Gal-(1->3)-O-[O-beta-D-Gal-(1->4)-2-(acetylamino)-2-deoxy-beta-D-Glc-(1->6)]-2-(acetylamino)-2-deoxy-D-Gal
ClassSmall Molecule
DescriptionO-b-D-galactopyranosyl-(1->3)-O-[O-b-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1->6)]-2-(acetylamino)-2-deoxy- D-Galactose is a milk oligosaccharide alditol derived from mucin glycoprotein detected with High-performance anion exchange-chromatography. (PMID: 1799211). Forms part of carbohydrate chains linked to human kappa-casein from mature milk. (PMID: 3342257). A neutral oligosaccharides from human milk of O-linked glycoproteins having blood group A and H activities. (PMID: 1904864).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
O-b-D-Galactopyranosyl-(1->3)-O-[O-b-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1->6)]-2-(acetylamino)-2-deoxy- D-galactoseHMDB
O-beta-D-Galactopyranosyl-(1->3)-O-[O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->6)]-2-(acetylamino)-2-deoxy- D-galactoseHMDB
N-[(3R,4S,5R)-4,5-Dihydroxy-6-{[(2R,3R,4R,6R)-4-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-{[(2S,3R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexan-2-yl]ethanimidateGenerator, HMDB
O-b-D-Gal-(1->3)-O-[O-b-D-gal-(1->4)-2-(acetylamino)-2-deoxy-b-D-GLC-(1->6)]-2-(acetylamino)-2-deoxy-D-galGenerator, HMDB
O-Β-D-gal-(1->3)-O-[O-β-D-gal-(1->4)-2-(acetylamino)-2-deoxy-β-D-GLC-(1->6)]-2-(acetylamino)-2-deoxy-D-galGenerator, HMDB
Chemical FormulaC28H48N2O21
Average Molecular Mass748.682 g/mol
Monoisotopic Mass748.275 g/mol
CAS Registry Number90393-60-5
IUPAC NameN-[(3R,4S,5R)-6-{[(2R,3R,4R,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexan-2-yl]acetamide
Traditional NameN-[(3R,4S,5R)-6-{[(2R,3R,4R,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexan-2-yl]acetamide
SMILESCC(=O)NC(C=O)[C@@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@@H](O)[C@H](O)CO[C@@H]1O[C@H](CO)C(O[C@@H]2O[C@H](CO)C(O)C(O)[C@H]2O)[C@H](O)[C@H]1NC(C)=O
InChI IdentifierInChI=1S/C28H48N2O21/c1-8(35)29-10(3-31)24(50-27-22(44)20(42)17(39)12(4-32)47-27)16(38)11(37)7-46-26-15(30-9(2)36)19(41)25(14(6-34)49-26)51-28-23(45)21(43)18(40)13(5-33)48-28/h3,10-28,32-34,37-45H,4-7H2,1-2H3,(H,29,35)(H,30,36)/t10?,11-,12-,13-,14-,15-,16+,17+,18?,19-,20+,21?,22-,23-,24-,25?,26-,27+,28+/m1/s1
InChI KeyHKHAQIZMVCMZAO-KMKHDUTPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acyl-alpha-hexosamines
Alternative Parents
Substituents
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • N-acyl-alpha-hexosamine
  • Alkyl glycoside
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty acyl
  • Oxane
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Carbonyl group
  • Aldehyde
  • Primary alcohol
  • Organic nitrogen compound
  • 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 Solubility78.3 g/LALOGPS
logP-2.5ALOGPS
logP-9.5ChemAxon
logS-0.98ALOGPS
pKa (Strongest Acidic)11.28ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area373.41 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity156.79 m³·mol⁻¹ChemAxon
Polarizability71.5 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-3314126900-3d497138c5f6418ba85eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_13) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_14) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_15) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015i-0000190400-e68139f40780731743d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-1330490100-79cb1b968e1d38a42dc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00yi-0160961100-601540cd909a3bc5d47cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fmi-0589520700-0c6542c3c22cec3b7019Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-3955360800-29ec1017fa67bf6e2ed2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-2609500000-cd36ffcef8d8d6ed8086Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1100121900-54c27aab5384bf1adab6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-9412115300-ba3b4f0966aa8328c3ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-4410930000-45b7d5e270edd9c5e157Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0301180900-796831749f05d4527516Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2500590400-2ab2377bcd2b45316375Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-9801155100-bb51ddb300e89b8ffb48Spectrum
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
1D NMR1H 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 IDHMDB0002067
FooDB IDFDB022829
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17216158
ChEBI ID169604
PubChem Compound ID22833581
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Maaheimo, Hannu; Penttilae, Leena; Renkonen, Ossi. Enzyme-aided construction of medium-sized alditols of complete O-linked saccharides Galb1-4GlcNAcb1-6Galb1-4GlcNAcb1-6(Galb1-3)GalNAc-ol resists the action of endo-b-galactosidase from Bacteroides fragilis. The constructed hexasaccharide alditol. FEBS Letters (1994), 349(1), 55-9.
2. Reddy GP, Bush CA: High-performance anion exchange-chromatography of neutral milk oligosaccharides and oligosaccharide alditols derived from mucin glycoproteins. Anal Biochem. 1991 Nov 1;198(2):278-84.
3. Saito T, Itoh T, Adachi S: Chemical structure of neutral sugar chains isolated from human mature milk kappa-casein. Biochim Biophys Acta. 1988 Feb 17;964(2):213-20.
4. Amano J, Straehl P, Berger EG, Kochibe N, Kobata A: Structures of mucin-type sugar chains of the galactosyltransferase purified from human milk. Occurrence of the ABO and Lewis blood group determinants. J Biol Chem. 1991 Jun 25;266(18):11461-77.