Difucosyllacto-N-hexaose a (CHEM036180)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:17:32 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036180
Identification
Common NameDifucosyllacto-N-hexaose a
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DFLNH aHMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->3)-O-[beta-D-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->6)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)]-O-beta-D-galactopyranosyl-(1->4)- D-glucoseHMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->3)-O-[beta-delta-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->6)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->2)-O-beta-delta-galactopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)]-O-beta-delta-galactopyranosyl-(1->4)- D-glucoseHMDB
N-[(2R,3R,5S,6R)-4-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-{[(2R,3R,4R,5R,6S)-3-hydroxy-2-({[(2R,3R,4R,5S,6R)-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3S,4R,5S,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-5-methyl-6-{[(2R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]ethanimidateHMDB
Chemical FormulaC52H88N2O39
Average Molecular Mass1365.245 g/mol
Monoisotopic Mass1364.496 g/mol
CAS Registry Number125091-31-8
IUPAC NameN-[(2R,3R,5S,6R)-4-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2-{[(2R,3R,4R,5R,6S)-2-({[(2R,3R,4R,5S,6R)-3-acetamido-6-(hydroxymethyl)-4-{[(2R,3S,4R,5S,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3-hydroxy-5-methyl-6-{[(2R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional NameN-[(2R,3R,5S,6R)-4-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2-{[(2R,3R,4R,5R,6S)-2-({[(2R,3R,4R,5S,6R)-3-acetamido-6-(hydroxymethyl)-4-{[(2R,3S,4R,5S,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3-hydroxy-5-methyl-6-{[(2R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
SMILES[H][C@@](O)(CO)C(O[C@]1([H])O[C@]([H])(CO[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]3([H])O)[C@]([H])(O[C@]3([H])O[C@@]([H])(O)[C@@]([H])(O)[C@@]([H])(O)[C@]3([H])O)[C@@]2([H])NC(C)=O)[C@]([H])(O)[C@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)C(O[C@]3([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]3([H])O[C@]3([H])O[C@@]([H])(C)[C@@]([H])(O)[C@@]([H])(O)[C@]3([H])O)[C@@]2([H])NC(C)=O)[C@@]1([H])C)[C@]([H])(O)[C@@]([H])(O)C=O
InChI IdentifierInChI=1S/C52H88N2O39/c1-12-39(87-48-23(53-14(3)61)42(29(69)20(9-59)82-48)90-52-44(34(74)28(68)19(8-58)84-52)92-49-36(76)31(71)25(65)13(2)81-49)30(70)22(86-46(12)88-40(17(64)6-56)26(66)16(63)5-55)11-80-47-24(54-15(4)62)43(91-51-38(78)33(73)35(75)45(79)93-51)41(21(10-60)85-47)89-50-37(77)32(72)27(67)18(7-57)83-50/h5,12-13,16-52,56-60,63-79H,6-11H2,1-4H3,(H,53,61)(H,54,62)/t12-,13+,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?,41-,42?,43-,44-,45-,46+,47-,48+,49+,50+,51-,52+/m1/s1
InChI KeyOAXMVFUPLMUHGJ-AHOWPFSISA-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
  • Hemiacetal
  • 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 Solubility124 g/LALOGPS
logP-1.8ALOGPS
logP-14ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)11.01ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count39ChemAxon
Hydrogen Donor Count24ChemAxon
Polar Surface Area649.55 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity283.08 m³·mol⁻¹ChemAxon
Polarizability128.37 ųChemAxon
Number of Rings7ChemAxon
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, Positivesplash10-0f72-7947000020-9e7f5b6b7d18dd04fbbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9b-9522000031-118ec7500fd017af8670Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pba-9623000021-7a8c8654a2d7201fe150Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ds-5579000000-2d9f667bb7a9468c2d09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3539101111-b952987942900c1ededeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-2501092602-9ee69ec16a21404525ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1359000000-315a38691b94936a83feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi0-6395000000-fd1345320a74c5d4e0ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9221000011-54ee59f7c744cf8c6f9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxs-5966000000-36f4ac0d854cc74898b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9431000000-79bd0dc0b7124d4c30fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000e-9222000000-09b6a12ac246de643637Spectrum
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 IDHMDB0006622
FooDB IDFDB024011
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID58145714
ChEBI ID88470
PubChem Compound ID124202089
Kegg Compound IDG01889
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Strecker, Gerard; Wieruszeski, Jean Michel; Michalski, Jean Claude; Montreuil, Jean. Primary structure of human milk nona- and decasaccharides determined by a combination of fast atom bombardment mass spectrometry and proton/carbon-13-nuclear magnetic resonance spectroscopy. Evidence for a new core structure, iso-lacto-N-octaose. Glycoconjugate Journal (1989), 6(2), 169-82.
2. Nakajima K, Kinoshita M, Matsushita N, Urashima T, Suzuki M, Suzuki A, Kakehi K: Capillary affinity electrophoresis using lectins for the analysis of milk oligosaccharide structure and its application to bovine colostrum oligosaccharides. Anal Biochem. 2006 Jan 1;348(1):105-14. Epub 2005 Oct 26.
3. Kim HM, Kim IJ, Danishefsky SJ: Total syntheses of tumor-related antigens N3: probing the feasibility limits of the glycal assembly method. J Am Chem Soc. 2001 Jan 10;123(1):35-48.
4. Bruntz R, Dabrowski U, Dabrowski J, Ebersold A, Peter-Katalinic J, Egge H: Fucose-containing oligosaccharides from human milk from a donor of blood group 0 Le(a) nonsecretor. Biol Chem Hoppe Seyler. 1988 Apr;369(4):257-73.
5. Yu H, Sipes JM, Cashel J, Bakos MA, Goldblum RM, Roberts DD: Recognition of type 1 chain oligosaccharides and lacto-series glycolipids by an antibody to human secretory component. Arch Biochem Biophys. 1995 Oct 1;322(2):299-305.