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Showing Compound Difucosyllacto-N-hexaose b (FDB024008)

Record Information
Version1.0
Creation date2011-09-21 00:38:24 UTC
Update date2015-07-21 06:57:58 UTC
Primary IDFDB024008
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDifucosyllacto-N-hexaose b
DescriptionDifucosyllacto-N-hexaose b is a fucosyl-oligosaccharide from human breast milk. For several years biochemical studies on the carbohydrate composition of human milk have concerned only the dosage of lactose. In fact, even though oligosaccharides had already been identified at the end of the 19th century, the methods available at that time did not allow further data to be obtained on their precise amounts. The availability of more advanced techniques has recently made it possible to establish the precise amount of oligosaccharides in human milk during the different phases of lactation. The results obtained so far have quantified the concentration of such substances at 20 to 23 g l-1 in colostrum and 12 to 14 g l-1 in mature milk; thus, from the quantitative point of view, oligosaccharides represent the third component of human milk, following lactose and lipids. However, even though improvements have been made regarding the total amount of oligosaccharides, knowledge on the amount of each oligosaccharide in human milk remains inadequate. From the biochemical point of view, such substances result from the sequential addition of monosaccharides to the molecule of lactose, by specific glycosyltransferases of the mammary gland. In particular, monosaccharidic units represented by fucose (Fuc), galactose (Gal), N-acetylglucosamine (GlcNac) and sialic acid (NANA) are added to lactose, forming oligosaccharides of different dimensions, with a linear or ramified molecular structure. Such a synthetic process leads to the formation of a significant number of oligosaccharides. More than 80 oligosaccharides have already been identified which, on the basis of their chemical composition, can be classified as follows: (i) "core" oligosaccharides, made up of Glc, Gal and GlcNac, representing the starting structures for the synthesis of more complex oligosaccharides; (ii) fucosyl-oligosaccharides, deriving from the addition to the core of one or more molecules of Fuc; (iii) sialyloligosaccharides, resulting from the addition to the core of one or more molecules of NANA; and (iv) sialylfucosyl-oligosaccharides, containing both Fuc and NANA. The presence and the quantity of different types of oligosaccharides in human milk are genetically determined and closely related to the secretor state A, B, H and Lewis, with significant differences among the different genotypes. The most common phenotype, present in 70% of the general population, is represented by subjects expressing both the secretor and Lewis gene. The milk produced by these mothers is the richest in oligosaccharides. It is evidently difficult to analyse oligosaccharides of human milk as they are numerous and have a particularly complex structure. The data available until now demonstrate that the majority of human milk oligosaccharides is made up of molecules with three to nine monosaccharidic units (trisaccharides to nonasaccharides). (PMID:10569230) [HMDB]
CAS Number98359-76-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility257 g/LALOGPS
logP-1.9ALOGPS
logP-13ChemAxon
logS-0.73ALOGPS
pKa (Strongest Acidic)5.15ChemAxon
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
Polarizability129.64 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC52H88N2O39
IUPAC nameN-[(2R,3R,4R,5S,6R)-2-{[(3S,5R,6S)-3,5-dihydroxy-4-{[(2S,3R,4R,5S,6R)-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(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
InChI IdentifierInChI=1S/C52H88N2O39/c1-12-25(65)31(71)35(75)48(81-12)89-42-21(10-60)86-47(24(54-15(4)62)44(42)92-51-38(78)34(74)29(69)19(8-58)84-51)93-45-30(70)22(87-52(39(45)79)88-40(17(64)6-56)27(67)16(63)5-55)11-80-46-23(53-14(3)61)43(91-49-36(76)32(72)26(66)13(2)82-49)41(20(9-59)85-46)90-50-37(77)33(73)28(68)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-/m0/s1
InChI KeyBCENFJUGBDUPJS-JTGDLCLGSA-N
Isomeric SMILES[H][C@@](O)(CO)[C@@]([H])(O[C@]1([H])OC(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])(C)[C@@]([H])(O)[C@@]([H])(O)[C@]3([H])O)[C@@]2([H])NC(C)=O)[C@]([H])(O)C(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O[C@]3([H])O[C@@]([H])(C)[C@@]([H])(O)[C@@]([H])(O)[C@]3([H])O)[C@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]3([H])O)[C@@]2([H])NC(C)=O)[C@@]1([H])O)[C@]([H])(O)[C@@]([H])(O)C=O
Average Molecular Weight1365.2451
Monoisotopic Molecular Weight1364.496421084
Classification
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
  • N-acyl-alpha-hexosamine
  • Fatty acyl glycoside
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Fatty acyl
  • Oxane
  • Beta-hydroxy aldehyde
  • Acetamide
  • Alpha-hydroxyaldehyde
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Acetal
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53477876
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06619
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference