O-2-(Acetylamino)-2-deoxy-alpha-D-Gal-(1->3)-O-[6-deoxy-alpha-L-Gal-(1->2)]-O-beta-D-Gal-(1->3)-O-2-(acetylamino)-2-deoxy-beta-D-Glc-(1->3)-O-beta-D-Gal-(1->4)-D-Glc (CHEM035321)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:39:36 UTC
Update Date2016-11-09 01:21:17 UTC
Accession NumberCHEM035321
Identification
Common NameO-2-(Acetylamino)-2-deoxy-alpha-D-Gal-(1->3)-O-[6-deoxy-alpha-L-Gal-(1->2)]-O-beta-D-Gal-(1->3)-O-2-(acetylamino)-2-deoxy-beta-D-Glc-(1->3)-O-beta-D-Gal-(1->4)-D-Glc
ClassSmall Molecule
DescriptionO-2-(acetylamino)-2-deoxy-a-D-galactopyranosyl-(1->3)-O-[6-deoxy-a-L-galactopyranosyl-(1->2)]-O-b-D-galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1->3)-O-b-D-galactopyranosyl-(1->4)-D-Glucose is a fucose-containing oligosaccharide found in human milk. (PMID: 11308023). Is a blood group specific oligosaccharide from feces of a blood group A breast-fed infant. (PMID: 6513935).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
O-2-(acetylamino)-2-Deoxy-a-D-galactopyranosyl-(1->3)-O-[6-deoxy-a-L-galactopyranosyl-(1->2)]-O-b-D-galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1->3)-O-b-D-galactopyranosyl-(1->4)-D-glucoseHMDB
O-2-(acetylamino)-2-Deoxy-alpha-D-galactopyranosyl-(1->3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->2)]-O-beta-D-galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucoseHMDB
N-[(2R,3R,4R,5R,6R)-2-{[(3R,4S,5S,6R)-2-{[(2S,3R,4R,5S,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-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidateGenerator, HMDB
O-2-(Acetylamino)-2-deoxy-a-D-gal-(1->3)-O-[6-deoxy-a-L-gal-(1->2)]-O-b-D-gal-(1->3)-O-2-(acetylamino)-2-deoxy-b-D-GLC-(1->3)-O-b-D-gal-(1->4)-D-GLCGenerator
O-2-(Acetylamino)-2-deoxy-α-D-gal-(1->3)-O-[6-deoxy-α-L-gal-(1->2)]-O-β-D-gal-(1->3)-O-2-(acetylamino)-2-deoxy-β-D-GLC-(1->3)-O-β-D-gal-(1->4)-D-GLCGenerator
Chemical FormulaC40H68N2O30
Average Molecular Mass1056.963 g/mol
Monoisotopic Mass1056.386 g/mol
CAS Registry Number88972-42-3
IUPAC NameN-[(2S,3R,4R,5S,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-{[(3R,4S,5S,6R)-4-{[(2R,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional NameN-[(2S,3R,4R,5S,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-{[(3R,4S,5S,6R)-4-{[(2R,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
SMILES[H][C@@](O[C@@H]1O[C@H](CO)[C@H](O)[C@]([H])(O[C@@H]2O[C@H](CO)[C@@H](O)[C@]([H])(OC3O[C@H](CO)[C@H](O)[C@H](O[C@@]4([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]4NC(C)=O)[C@H]3O[C@]3([H])O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]3O)[C@H]2NC(C)=O)[C@H]1O)([C@H](O)CO)[C@H](O)[C@@H](O)C=O
InChI IdentifierInChI=1S/C40H68N2O30/c1-10-21(53)28(60)29(61)38(63-10)72-35-34(71-36-19(41-11(2)49)27(59)23(55)15(6-45)64-36)26(58)18(9-48)67-40(35)69-32-20(42-12(3)50)37(65-16(7-46)24(32)56)70-33-25(57)17(8-47)66-39(30(33)62)68-31(14(52)5-44)22(54)13(51)4-43/h4,10,13-40,44-48,51-62H,5-9H2,1-3H3,(H,41,49)(H,42,50)/t10-,13-,14+,15+,16+,17+,18+,19+,20+,21+,22+,23-,24+,25-,26-,27+,28+,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,39-,40?/m0/s1
InChI KeyUCLWMVLXXHCQHW-JMJWVNOBSA-N
Chemical Taxonomy
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
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 Solubility98.6 g/LALOGPS
logP-2.1ALOGPS
logP-12ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)11.32ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count30ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area511.48 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity220.07 m³·mol⁻¹ChemAxon
Polarizability100.03 ųChemAxon
Number of Rings5ChemAxon
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, Negativesplash10-002r-9200000155-1c85772987cf14db4659Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02br-9601010013-86f64f4334c1e31de2a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-5921400000-279690115fc24f9faa00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9100000004-b297d573d728ba59d0a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6u-9310000063-2597788a9eb9bce74487Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000002-9868bbad352af3d8cbccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01sd-8901070063-02c94524319e0b211089Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01sl-4903050151-d82519749056f81710c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qi-7902130033-9991e3bee086afa1a58bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0770-9400000040-6740981093abe8ccb9d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9500000120-0aa4070d5cca458b093eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-024j-9700000010-62a0406135949a7ccfebSpectrum
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 IDHMDB0002071
FooDB IDFDB022831
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013042
ChEBI IDNot Available
PubChem Compound ID53477742
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Suzuki, Minoru; Suzuki, Akemi. Structural characterization of fucose-containing oligosaccharides by high-performance liquid chromatography and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Biological Chemistry (2001), 382(2), 251-257.
2. Suzuki M, Suzuki A: Structural characterization of fucose-containing oligosaccharides by high-performance liquid chromatography and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Biol Chem. 2001 Feb;382(2):251-7.
3. Sabharwal H, Nilsson B, Chester MA, Sjoblad S, Lundblad A: Blood group specific oligosaccharides from faeces of a blood group A breast-fed infant. Mol Immunol. 1984 Nov;21(11):1105-12.