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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-13 02:07:01 UTC
HMDB IDHMDB00048
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 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 ).
Structure
Thumb
Synonyms
ValueSource
(Gal)1 (GLC)1ChEBI
6-O-(alpha-D-Galactopyranosyl)-D-glucopyranoseChEBI
6-O-alpha-D-Galactopyranosyl-D-glucopyranoseChEBI
alpha-D-Gal-(1->6)-D-GLCChEBI
alpha-D-Galactosyl-(1->6)-D-glucoseChEBI
alpha-D-Galp-(1->6)-D-GLCPChEBI
D-MelibioseChEBI
Gal-alpha(1,6)GLCChEBI
6-(a-D-galactosido)-D-GlucoseHMDB
6-(a-delta-galactosido)-delta-GlucoseHMDB
6-(D-galactosido)-D-GlucoseHMDB
6-(D-galactosido)-delta-GlucoseHMDB
6-O-a-D-Galactopyranosyl-D-glucoseHMDB
6-O-alpha-D-Galactopyranosyl-D-glucoseHMDB
6-O-alpha-delta-Galactopyranosyl-delta-glucoseHMDB
6-O-HexopyranosylhexoseHMDB
alpha-D-MelibioseHMDB
alpha-delta-MelibioseHMDB
alpha-MelibioseHMDB
D-(+)-MelibioseHMDB
delta-(+)-MelibioseHMDB
delta-MelibioseHMDB
MellibioseHMDB
Chemical FormulaC12H22O11
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
IUPAC Name(3R,4S,5S,6R)-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol
Traditional NameD-melibiose
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 KeyInChIKey=DLRVVLDZNNYCBX-ABXHMFFYSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point84 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility511.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.34 m3·mol-1ChemAxon
Polarizability30.97 Å3ChemAxon
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)splash10-0wmj-0951000000-0023b7689b93195cc520View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)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
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-03di-0901000000-f6e7873e48c702625149View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-01p6-9400000000-eeaeb67af95c15b24dbcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-000i-9100000000-9b6ce73cdaa5b27bded7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Urine
Tissue Location
  • Spleen
  • Tissues Containing Microbial Flora
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043map00052
GalactosemiaSMP00182Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified< 0.1 umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001204
KNApSAcK IDC00001142
Chemspider ID389538
KEGG Compound IDC05402
BioCyc IDMELIBIOSE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00048
Metagene LinkHMDB00048
METLIN ID3478
PubChem Compound440658
PDB IDNot Available
ChEBI ID28053
References
Synthesis ReferencePictet, Ame; Vogel, Hans. The synthesis of melibiose. Helvetica Chimica Acta (1927), 10 280.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Almeida IC, Milani SR, Gorin PA, Travassos LR: Complement-mediated lysis of Trypanosoma cruzi trypomastigotes by human anti-alpha-galactosyl antibodies. J Immunol. 1991 Apr 1;146(7):2394-400. [1706399 ]
  2. Sharma A, Ahmed H, Allen HJ: Isolation of a melibiose-binding protein from human spleen. Glycoconj J. 1995 Feb;12(1):17-21. [7795409 ]
  3. Steuer MK, Steuer M, Bonkowsky V, Gabius HJ, Hofstadter F: Characterization of sugar receptor expression by neoglycoproteins in oral and oropharyngeal squamous cell carcinomas. Eur Arch Otorhinolaryngol. 1995;252(5):292-7. [7576587 ]
  4. Vaughan HA, Loveland BE, Sandrin MS: Gal alpha(1,3)Gal is the major xenoepitope expressed on pig endothelial cells recognized by naturally occurring cytotoxic human antibodies. Transplantation. 1994 Oct 27;58(8):879-82. [7524207 ]
  5. Barboza Junior MS, Silva TM, Guerrant RL, Lima AA: Measurement of intestinal permeability using mannitol and lactulose in children with diarrheal diseases. Braz J Med Biol Res. 1999 Dec;32(12):1499-504. [10585631 ]
  6. Furukawa K, Ying R, Nakajima T, Matsuki T: Hemagglutinins in fungus extracts and their blood group specificity. Exp Clin Immunogenet. 1995;12(4):223-31. [8919354 ]
  7. Gibbons RJ, Qureshi JV: Inhibition of adsorption of Streptococcus mutans strains to saliva-treated hydroxyapatite by galactose and certain amines. Infect Immun. 1979 Dec;26(3):1214-7. [528053 ]
  8. Nicolopoulou A, Zoumbou K, Papageorgacopoulou N, Papapetropoulou M: Metabolic and compositional changes in Escherichia coli cells starved in seawater. Microbiol Res. 1994 Nov;149(4):343-50. [7842233 ]
  9. Wu AM, Song SC, Chen YY, Gilboa-Garber N: Defining the carbohydrate specificities of aplysia gonad lectin exhibiting a peculiar D-galacturonic acid affinity. J Biol Chem. 2000 May 12;275(19):14017-24. [10799474 ]
  10. Rietra PJ, Van den Bergh FA, Tager JM: Properties of the residual alpha-galactosidase activity in the tissues of a Fabry hemizygote. Clin Chim Acta. 1975 Aug 4;62(3):401-13. [809216 ]
  11. Colby SM, Harrington DJ, Russell RR: Identification and genetic characterisation of melibiose-negative isolates of Streptococcus mutans. Caries Res. 1995;29(5):407-12. [8521444 ]
  12. 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 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GLA
Uniprot ID:
P06280
Molecular weight:
Not Available
Reactions
Melibiose + Water → Beta-D-Galactose + D-Glucosedetails
D-Gal alpha 1->6D-Gal alpha 1->6D-Glucose + Water → Beta-D-Galactose + Melibiosedetails
General function:
Involved in catalytic activity
Specific function:
May serve as an alternate pathway for starch digestion when luminal alpha-amylase activity is reduced because of immaturity or malnutrition. May play a unique role in the digestion of malted dietary oligosaccharides used in food manufacturing.
Gene Name:
MGAM
Uniprot ID:
O43451
Molecular weight:
Not Available
General function:
Involved in catalytic activity
Specific function:
Has alpha-glucosidase activity.
Gene Name:
GANC
Uniprot ID:
Q8TET4
Molecular weight:
Not Available