Showing metabocard for Difucosyllactohexaose (BMDB0006618)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:24:17 UTC
Update Date2020-04-22 15:18:07 UTC
BMDB IDBMDB0006618
Secondary Accession Numbers
  • BMDB06618
Metabolite Identification
Common NameDifucosyllactohexaose
DescriptionDifucosyllactohexaose 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. Difucosyllactohexaose is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-[(3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-3,5-dihydroxy-4-{[(2S,3R,4S,6R)-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-2-yl]methoxy}-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]ethanimidateGenerator
Chemical FormulaC52H88N2O39
Average Molecular Weight1365.251
Monoisotopic Molecular Weight1364.496421022
IUPAC NameN-[(3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-3,5-dihydroxy-4-{[(2S,3R,4S,6R)-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-2-yl]methoxy}-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]ethanimidic acid
Traditional NameDFH
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(CO)[C@@]([H])(O[C@]1([H])O[C@]([H])(COC2([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])(C)[C@@]([H])(O)[C@@]([H])(O)[C@]3([H])O)[C@@]2([H])N=C(C)O)[C@]([H])(O)[C@@]([H])(O[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])(C)[C@@]([H])(O)[C@@]([H])(O)[C@]3([H])O)[C@@]2([H])N=C(C)O)[C@@]1([H])O)[C@]([H])(O)[C@@]([H])(O)C=O
InChI Identifier
InChI=1S/C52H88N2O39/c1-12-25(65)31(71)35(75)48(81-12)91-43-23(53-14(3)61)46(85-20(9-59)41(43)89-50-37(77)33(73)28(68)18(7-57)83-50)80-11-22-30(70)45(39(79)52(87-22)88-40(17(64)6-56)27(67)16(63)5-55)93-47-24(54-15(4)62)44(92-49-36(76)32(72)26(66)13(2)82-49)42(21(10-60)86-47)90-51-38(78)34(74)29(69)19(8-58)84-51/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-/m0/s1
InChI KeyXOHQYIKZIFWWAG-ZTLMKGMCSA-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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.9ALOGPS
logP-13ChemAxon
logS-0.73ALOGPS
pKa (Strongest Acidic)5.17ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count41ChemAxon
Hydrogen Donor Count24ChemAxon
Polar Surface Area656.53 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity284.4 m³·mol⁻¹ChemAxon
Polarizability128.62 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f72-3958000000-a1fa35a6f017b9f953a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pca-9733000010-32aaf595b2aed221c38dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-9522000000-9bb3cb9702e3cf561fc2View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound57504066
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceDua, Virendra K.; Goso, Kazue; Dube, Volker E.; Bush, C. Allen. Characterization of lacto-N-hexaose and two fucosylated derivatives from human milk by high-performance liquid chromatography and proton NMR spectroscopy. Journal of Chromatography (1985), 328 259-69.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available