Legend: 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 |
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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 |
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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 ![]() |
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BioCyc ID | MELIBIOSE ![]() |
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BiGG ID | Not Available | ||||||||||||||||||
Wikipedia Link | Not Available | ||||||||||||||||||
METLIN ID | 3478 ![]() |
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PubChem Compound | 440658 ![]() |
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PubChem Substance | 7769 ![]() |
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ChEBI ID | 28053 ![]() |
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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 Download FID (Varian) Show Experimental Conditions ![]() |
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Experimental 13C NMR Spectrum | Download Spectrum Download FID (Bruker) Show Experimental Conditions ![]() |
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Experimental 13C HSQC Spectrum | Download Spectrum Download FID (Bruker) Show Experimental Conditions ![]() |
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Predicted 1H NMR Spectrum |
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Predicted 13C NMR Spectrum |
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Mass Spectrum |
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Simplified TOCSY Spectrum | Not Available | ||||||||||||||||||
BMRB Spectrum | Not Available | ||||||||||||||||||
Cellular Location |
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Biofluid Location | Not Available | ||||||||||||||||||
Tissue Location |
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Concentrations (Normal) | Not Available | ||||||||||||||||||
Concentrations (Abnormal) | Not Available | ||||||||||||||||||
Pathway Names |
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HMDB Pathways |
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KEGG Pathways |
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SimCell Pathways |
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General References | Not Available |