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Human Metabolome Database Version 3.5

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Showing metabocard for Difucosyl-para-N-hexaose (HMDB06616)

Record Information
Version 3.5
Creation Date 2007-05-25 05:37:31 -0600
Update Date 2013-02-08 17:15:06 -0700
HMDB ID HMDB06616
Secondary Accession Numbers None
Metabolite Identification
Common Name Difucosyl-para-N-hexaose
Description Difucosyl-para-N-hexaose is a difuco oligosaccharide-derivative of lacto-N-hexaose isolated from human breast milk. After lactose and lipids, human milk oligosaccharides are quantitatively the third largest and most diverse component of breast milk. Human colostrum is known to be important for the protection of infants against infection by pathogenic microorganisms. Their compositions are largely dependent on the blood type of the lactating mother. These oligosaccharides can be classified as either "acidic" or "neutral," depending on the presence or absence of sialic acid moieties. Moderate-to-severe diarrhea of all causes occurs less often in infants whose milk contains high levels of total 2-linked fucosyloligosaccharides as a percent of milk oligosaccharide. (PMID: 17915960 Link_out, 11273599 Link_out, 3401331 Link_out, 11273599 Link_out, 7574700 Link_out; 8953162; 3839799, 9458328).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Difucosyl-p-lacto-N-hexaose
  2. Difucosyl-para-N-hexaose
  3. O-6-Deoxy-alpha-L-galactopyranosyl-(1->3)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)- D-Glucose
  4. O-6-Deoxy-alpha-L-galactopyranosyl-(1->3)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-beta-delta-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)- D-Glucose
Chemical Formula C52H88N2O39
Average Molecular Weight 1365.2451
Monoisotopic Molecular Weight 1364.496421084
IUPAC Name N-[(2S,3R,5S,6R)-2-{[(2R,3S,4S,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-{[(2S,3R,5S,6R)-4-{[(2S,3R,4R,5S,6R)-3-acetamido-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}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)-4-{[(2S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide
Traditional IUPAC Name N-[(2S,3R,5S,6R)-2-{[(2R,3S,4S,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-{[(2S,3R,5S,6R)-4-{[(2S,3R,4R,5S,6R)-3-acetamido-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydr
CAS Registry Number 64309-01-9
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]3O[C@H](CO)[C@H](O)C(O[C@]4([H])O[C@H](CO)[C@@H](O[C@]5([H])O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]5O)[C@H](O[C@]5([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]5O)[C@H]4NC(C)=O)[C@H]3O)C(O[C@]3([H])O[C@@H](C)[C@@H](O)[C@@H](O)C3O)[C@H]2NC(C)=O)C1O)([C@H](O)CO)[C@H](O)[C@@H](O)C=O
InChI Identifier InChI=1S/C52H88N2O39/c1-12-25(66)31(72)34(75)48(80-12)88-40-21(10-60)85-47(24(54-15(4)63)43(40)91-50-36(77)33(74)28(69)18(7-57)82-50)93-45-30(71)20(9-59)84-52(38(45)79)89-41-22(11-61)86-46(23(53-14(3)62)42(41)90-49-35(76)32(73)26(67)13(2)81-49)92-44-29(70)19(8-58)83-51(37(44)78)87-39(17(65)6-56)27(68)16(64)5-55/h5,12-13,16-52,56-61,64-79H,6-11H2,1-4H3,(H,53,62)(H,54,63)/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 Key BCUMESVDMXHZRL-JUDCGFFFSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Oligosaccharides
Sub Class Hexose Oligosaccharides
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Aldehyde
  • Carboxamide Group
  • Fatty Acyl Glycoside
  • Glucosamine
  • Glycosyl Compound
  • Mannosamine
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct Parent Hexose Oligosaccharides
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 146 g/L ALOGPS
LogP -1.72 ALOGPS
LogP -14 ChemAxon
LogS -0.97 ALOGPS
pKa (strongest acidic) 11.29 ChemAxon
pKa (strongest basic) -3.9 ChemAxon
Hydrogen Acceptor Count 39 ChemAxon
Hydrogen Donor Count 24 ChemAxon
Polar Surface Area 649.55 A2 ChemAxon
Rotatable Bond Count 26 ChemAxon
Refractivity 283.35 ChemAxon
Polarizability 128.12 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB024006
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06616 Link_out
Metagene Link HMDB06616 Link_out
METLIN ID Not Available
PubChem Compound 53477874 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Sabharwal, Hemant; Nilsson, Bo; Groenberg, Gunnar; Chester, M. Alan; Dakour, Jamal; Sjoeblad, Sture; Lundblad, Arne. Oligosaccharides from feces of preterm infants fed on breast milk. Archives of Biochemistry and Biophysics (1988), 265(2), 390-406.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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. Pubmed: 7574700 Link_out
  2. Strecker G, Fievre S, Wieruszeski JM, Michalski JC, Montreuil J: Primary structure of four human milk octa-, nona-, and undeca-saccharides established by 1H- and 13C-nuclear magnetic resonance spectroscopy. Carbohydr Res. 1992 Mar 16;226(1):1-14. Pubmed: 1499015 Link_out
  3. Forchielli ML, Walker WA: The role of gut-associated lymphoid tissues and mucosal defence. Br J Nutr. 2005 Apr;93 Suppl 1:S41-8. Pubmed: 15877894 Link_out
  4. Yamashita K, Tachibana Y, Kobata A: Oligosaccharides of human milk. Structural studies of two new octasaccharides, difucosyl derivatives of para-lacto-N-hexaose and para-lacto-N-neohexaose. J Biol Chem. 1977 Aug 10;252(15):5408-11. Pubmed: 885859 Link_out