Record Information
Version1.0
Creation date2010-04-08 22:04:52 UTC
Update date2019-11-26 02:56:06 UTC
Primary IDFDB001204
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMelibiose
DescriptionIsolated from coffee beans, apple (Pyrus malus) and other plants 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). Melibiose is found in many foods, some of which are sesbania flower, mugwort, olive, and jerusalem artichoke.
CAS Number585-99-9
Structure
Thumb
Synonyms
Predicted PropertiesNot Available
Chemical FormulaC36H66O33
IUPAC name
InChI IdentifierInChI=1S/3C12H22O11/c13-1-4-5(15)6(16)9(19)12(22-4)21-2-3(14)10-7(17)8(18)11(20)23-10;13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4;13-1-4(15)7(17)8(18)5(16)3-22-12-11(21)10(20)9(19)6(2-14)23-12/h2*3-20H,1-2H2;1,4-12,14-21H,2-3H2
InChI KeyYFSMDFMEDLKMOS-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OCC(O)C(O)C(O)C(O)C=O)C(O)C(O)C1O.OCC1OC(OCC(O)C2OC(O)C(O)C2O)C(O)C(O)C1O.OCC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1O
Average Molecular Weight1026.8894
Monoisotopic Molecular Weight1026.348634638
Classification
Description Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Disaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Beta-hydroxy aldehyde
  • Oxane
  • Alpha-hydroxyaldehyde
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aldehyde
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-bc2f3b600f60e687a46a2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-bc2f3b600f60e687a46a2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-bc2f3b600f60e687a46a2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-e5a67b632bb21e28d52d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-e5a67b632bb21e28d52d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-e5a67b632bb21e28d52d2016-08-03View Spectrum
NMRNot Available
ChemSpider ID389538
ChEMBL IDNot Available
KEGG Compound IDC05402
Pubchem Compound ID440658
Pubchem Substance IDNot Available
ChEBI ID28053
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00048
CRC / DFC (Dictionary of Food Compounds) IDBWC12-V:BWC12-V
EAFUS IDNot Available
Dr. Duke IDMELIBIOSE
BIGG IDNot Available
KNApSAcK IDC00001142
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
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).