FComEx: Melibiose (PC000125)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:40 UTC

Update date

2017-01-19 02:36:13 UTC

FoodComEx ID

PC000125

FoodDB Record

FDB001204

Chemical Information

Name

Melibiose

Description

Isolated 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 Number

585-99-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(Gal)1 (glc)1	ChEBI
6-(a-D-galactosido)-D-glucose	biospider
6-(a-delta-galactosido)-delta-glucose	biospider
6-(D-galactosido)-D-glucose	biospider
6-(D-galactosido)-delta-glucose	biospider
6-O-(a-D-Galactopyranosyl)-D-glucopyranose	Generator
6-O-(alpha-D-Galactopyranosyl)-D-glucopyranose	biospider
6-O-(α-D-galactopyranosyl)-D-glucopyranose	Generator
6-O-a-D-Galactopyranosyl-D-glucopyranose	Generator
6-O-a-D-Galactopyranosyl-D-glucose	HMDB
6-O-alpha-D-Galactopyranosyl-D-glucopyranose	ChEBI
6-O-alpha-D-galactopyranosyl-D-Glucose	biospider
6-O-alpha-delta-galactopyranosyl-delta-Glucose	biospider
6-O-Hexopyranosylhexose	biospider
6-O-α-D-galactopyranosyl-D-glucopyranose	Generator
a-D-Gal-(1->6)-D-glc	Generator
a-D-Galactosyl-(1->6)-D-glucose	Generator
a-D-Galp-(1->6)-D-glcp	Generator
alpha-D-Gal-(1->6)-D-glc	ChEBI
alpha-D-Galactosyl-(1->6)-D-glucose	ChEBI
alpha-D-Galp-(1->6)-D-glcp	ChEBI
Alpha-d-melibiose	biospider
Alpha-delta-melibiose	biospider
Alpha-melibiose	biospider
D-(+)-melibiose	biospider
D-Gal-alpha1->6D-Glucose	biospider
D-Glucose, 6-O-α-D-galactopyranosyl-	biospider
D-melibiose	biospider
Delta-(+)-melibiose	biospider
Delta-melibiose	biospider
Gal-a(1,6)glc	Generator
Gal-alpha(1,6)glc	ChEBI
Gal-α(1,6)glc	Generator
Melibiose (van)	biospider
Melibiose, 8CI	db_source
Mellibiose	biospider
α-D-gal-(1->6)-D-glc	Generator
α-D-galactosyl-(1->6)-D-glucose	Generator
α-D-galp-(1->6)-D-glcp	Generator

Chemical Formula

C36H66O33

IUPAC name

2,3,4,5-tetrahydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanal; 2-[2-hydroxy-2-(3,4,5-trihydroxyoxolan-2-yl)ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol; 6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol

InChI Identifier

InChI=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 Key

YFSMDFMEDLKMOS-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(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 Weight

1026.8894

Monoisotopic Molecular Weight

1026.348634638

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents