You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Livestock Metabolome Database.
Record Information
Version1.0
Creation Date2016-07-13 19:40:34 UTC
Update Date2016-09-23 18:44:29 UTC
LmdbLMDB00018
Secondary Accession NumbersNone
Metabolite Identification
Common NameMelibiose
DescriptionMelibiose 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 animals, 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 ).
Structure
Thumb
Synonyms
ValueSource
6-O-(alpha-D-Galactopyranosyl)-D-mannopyranoseChEBI
6-O-alpha-D-Mannopyranosyl-alpha-D-galactopyranoseChEBI
6-O-(a-D-Galactopyranosyl)-D-mannopyranoseGenerator
6-O-(Α-D-galactopyranosyl)-D-mannopyranoseGenerator
6-O-a-D-Mannopyranosyl-a-D-galactopyranoseGenerator
6-O-Α-D-mannopyranosyl-α-D-galactopyranoseGenerator
Chemical FormulaC12H22O11
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
IUPAC Name(2S,3R,4S,5R,6R)-6-({[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol
Traditional Nameepimelibiose
CAS Registry Number585-99-9
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
InChI Identifier
InChI=1S/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-,11?,12+/m1/s1
InChI KeyDLRVVLDZNNYCBX-ABXHMFFYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3ALOGPS
logP-4.7ChemAxon
logS0.17ALOGPS
pKa (Strongest Acidic)11.25ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.34 m³·mol⁻¹ChemAxon
Polarizability31.32 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0uxr-0941000000-58f859df76fe1e87b22aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0udi-0941000000-58d4fa7d40972e66a89dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0wmj-0951000000-0023b7689b93195cc520View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0uxr-0941000000-1bcc10f21d6677bb0060View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS; 1 MEOX)splash10-00di-9741000000-a0071ea1c00218406733View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS; 1 MEOX)splash10-00di-9841000000-2028da966c304a1cd6cfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0941000000-58f859df76fe1e87b22aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0941000000-58d4fa7d40972e66a89dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0wmj-0951000000-0023b7689b93195cc520View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0941000000-1bcc10f21d6677bb0060View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9741000000-a0071ea1c00218406733View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9841000000-2028da966c304a1cd6cfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0wmj-0941000000-a42b8ddd325c04e1ac1aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0941000000-e12e0f47b8ab7a54784eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0iu0-2695000000-b644ad8ee930f0244c0fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-5652219000-e37450d07ee330d4fac3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-1709000000-e1aedea040f248898825View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9501000000-dfecff3e8858cc005d12View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-1e5c79ae513f06c8d563View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0309000000-5545d2826c364f86c437View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0902000000-842fab6069f2dd5af792View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ikd-6940000000-16b9872436436b7073aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1449000000-768cbc294d03684f91a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-5944000000-b042101ecaa99993cfe1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-9620000000-97071ace9e7da2591fd0View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB0000048
FooDB IDFDB001204
Phenol Explorer IDNot Available
KNApSAcK IDC00001142
BiGG IDNot Available
BioCyc IDMELIBIOSE
METLIN ID3478
PDB IDNot Available
Wikipedia LinkMelibiose
Chemspider ID389537
ChEBI ID4808
PubChem Compound ID440658
Kegg Compound IDC05402
YMDB IDYMDB02304
ECMDB IDECMDB21544
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tomita K, Nagura T, Okuhara Y, Nakajima-Adachi H, Shigematsu N, Aritsuka T, Kaminogawa S, Hachimura S: Dietary melibiose regulates th cell response and enhances the induction of oral tolerance. Biosci Biotechnol Biochem. 2007 Nov;71(11):2774-80. Epub 2007 Nov 7. [17986780 ]