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Bovine Metabolome Database



Showing metabocard for Melibiose (BMDB00048)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:39
Accession Number BMDB00048
Common Name Melibiose
Description Melibiose is disaccharide consisting of one galactose and one glucose moiety in an alpha (1-6) glycosidic linkage. This sugar is produced and metabolized only by enteric and lactic acid bacteria and other microbes. It is not an endogenous metabolite but may be obtained from the consumption of partially fermented molasses, brown sugar or honey. Antibodies to melibiose will appear in individuals affected by Chagas' disease (Trypanosoma cruzi infection). Melibiose is not metabolized by humans, but can be broken down by gut microflora, such as E. coli. In fact, E. coli is able to utilize melibiose as a sole source of carbon. Melibiose is first imported by the melibiose permease, MelB and then converted to β-D-glucose and β-D-galactose by the α-galactosidase encoded by melA. Because of its poor digestability Melibiose (along with rhamnose) can be used together for noninvasive intestinal mucosa barrier testing. This test can be used to assess malabsorption or impairment of intestinal permeability. Recent studies with dietary melibiose have shown that can strongly affected the Th cell responses to an ingested antigen. It has been suggested that melibiose could be used to enhance the induction of oral tolerance. (PMID 17986780)
Synonyms
  1. 6-(D-galactosido)-D-glucose
  2. 6-(a-D-galactosido)-D-glucose
  3. 6-O-Hexopyranosylhexose
  4. 6-O-a-D-galactopyranosyl-D-Glucose
  5. 6-O-alpha-D-galactopyranosyl-D-Glucose
  6. D-(+)-Melibiose
  7. D-Melibiose
  8. Melibiose
  9. Mellibiose
  10. alpha-D-Melibiose
  11. alpha-Melibiose
  12. 6-(D-galactosido)-delta-glucose
  13. 6-(a-delta-galactosido)-delta-glucose
  14. 6-O-alpha-delta-galactopyranosyl-delta-Glucose
  15. delta-(+)-Melibiose
  16. delta-Melibiose
  17. alpha-delta-Melibiose
Chemical IUPAC Name 2,3,4,5-tetrahydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hexanal
Chemical Formula C12H22O11
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Carbohydrates and Carbohydrate conjugates
Class
  • Carbohydrates
Sub Class
  • Disaccharides
Family
  • Microbial_Metabolite
Species
  • hemiacetal; acetal; primary alcohol; secondary alcohol; 1,2-diol; heterocyclic compound
Biofunction
Application
Source
  • Exogenous
Average Molecular Weight 342.297
Monoisotopic Molecular Weight 342.116211
Isomeric SMILES OC[C@H]1O[C@H](OC[C@H]2OC(O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O
Canonical SMILES OCC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1O
KEGG Compound ID C05402 Link Image
BioCyc ID MELIBIOSE Link Image
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 3478 Link Image
PubChem Compound 440658 Link Image
PubChem Substance 7769 Link Image
ChEBI ID 28053 Link Image
CAS Registry Number 585-99-9
InChI Identifier InChI=1/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5+,6-,7+,8+,9-,10-,11u,12+/m1/s1
Synthesis Reference Pictet, Ame; Vogel, Hans. The synthesis of melibiose. Helvetica Chimica Acta (1927), 10 280.
Melting Point (Experimental) 84 oC
Experimental Water Solubility 1000.0 mg/mL [MERCK INDEX (1996)] Source: PhysProp
Predicted Water Solubility 511.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -3.00 [Predicted by ALOGPS]; -4.1 [Predicted by PubChem via XLOGP]; -5.30 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Download Spectrum
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Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
Not Available
Predicted 13C NMR Spectrum Show Image
Not Available
Mass Spectrum
Low Energy
Download File
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Extracellular
  • Cytoplasm (Predicted from LogP)
Biofluid Location Not Available
Tissue Location
Tissue References
Spleen
Tissues Containing Microbial Flora
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Galactose Metabolism
HMDB Pathways
Name Galactose Metabolism
Image Show Link Image
KEGG Pathways
Name Galactose Metabolism
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SimCell Pathways
Name Galactose Metabolism
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Graph
SBML
General References Not Available