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Bovine Metabolome Database

Showing metabocard for Melibiose (BMDB00048)

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	6-(D-galactosido)-D-glucose 6-(a-D-galactosido)-D-glucose 6-O-Hexopyranosylhexose 6-O-a-D-galactopyranosyl-D-Glucose 6-O-alpha-D-galactopyranosyl-D-Glucose D-(+)-Melibiose D-Melibiose Melibiose Mellibiose alpha-D-Melibiose alpha-Melibiose 6-(D-galactosido)-delta-glucose 6-(a-delta-galactosido)-delta-glucose 6-O-alpha-delta-galactopyranosyl-delta-Glucose delta-(+)-Melibiose delta-Melibiose 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
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
BioCyc ID	MELIBIOSE
BiGG ID	Not Available
Wikipedia Link	Not Available
METLIN ID	3478
PubChem Compound	440658
PubChem Substance	7769
ChEBI ID	28053
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)	Show PDF/HTML
MOL File	Show
SDF File	Show
PDB File	Show
2D Structure
3D Structure
Experimental PDB ID	Not Available
Experimental 1H NMR Spectrum	Download Spectrum Download FID (Varian) Show Experimental Conditions
Experimental 13C NMR Spectrum	Download Spectrum Download FID (Bruker) Show Experimental Conditions
Experimental 13C HSQC Spectrum	Download Spectrum Download FID (Bruker) Show Experimental Conditions
Predicted 1H NMR Spectrum	Show Image Not Available
Predicted 13C NMR Spectrum	Show Image Not Available
Mass Spectrum	Low Energy Download File Show Experimental Conditions Medium Energy Download File Show Experimental Conditions High Energy Download File Show Experimental Conditions
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
KEGG Pathways	Name Galactose Metabolism Image Show
SimCell Pathways	Name Galactose Metabolism Image Show Graph SBML
General References	Not Available

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