melibiose (CHEBI:28053)

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ChEBI Name	melibiose

ChEBI ID	CHEBI:28053

Definition	A glycosylglucose formed by an α-(1→6)-linkage between D-galactose and D-glucose.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:6733, CHEBI:60170, CHEBI:25182, CHEBI:20943

Supplier Information	eMolecules:6884510

Download	Molfile XML SDF

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Wikipedia	License
Melibiose is a reducing disaccharide formed by an α-1,6 linkage between galactose and glucose (D-Gal-(α1→6)-D-Glc). It differs from lactose in the chirality of the carbon where the galactose ring is closed and that the galactose is linked to a different point on the glucose moiety. It can be formed by invertase-mediated hydrolysis of raffinose, which produces melibiose and fructose. Melibiose can be broken down into its component saccharides, glucose and galactose, by the enzyme alpha-galactosidase, such as MEL1 from Saccharomyces pastorianus (lager yeast). Melibiose cannot be used by Saccharomyces cerevisiae (ale yeast), so this is one test to differentiate between the two yeast species.
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Formulae

C12H22O11
C12H22O11

Net Charge

Average Mass

342.29650

Monoisotopic Mass

342.11621

InChI

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

InChIKey

DLRVVLDZNNYCBX-ABXHMFFYSA-N

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

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. elastin-laminin receptor agonist An agonist that selectively binds to and activates elastin-laminin receptors.

ChEBI Ontology
Outgoing	melibiose (CHEBI:28053) has role Escherichia coli metabolite (CHEBI:76971) melibiose (CHEBI:28053) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) melibiose (CHEBI:28053) has role elastin-laminin receptor agonist (CHEBI:91139) melibiose (CHEBI:28053) has role mouse metabolite (CHEBI:75771) melibiose (CHEBI:28053) has role plant metabolite (CHEBI:76924) melibiose (CHEBI:28053) is a glycosylglucose (CHEBI:24405)

Incoming	α-D-Galp-(1→3)-[α-D-Galp-(1→6)]-D-Glcp (CHEBI:148118) has functional parent melibiose (CHEBI:28053) melibionic acid (CHEBI:75299) has functional parent melibiose (CHEBI:28053) royal jelly (CHEBI:78665) has part melibiose (CHEBI:28053) β-melibiose (CHEBI:61827) is a melibiose (CHEBI:28053)

IUPAC Name

α-D-galactopyranosyl-(1→6)-D-glucopyranose

Synonyms	Sources
(Gal)1 (Glc)1	KEGG GLYCAN
6-O-(alpha-D-Galactopyranosyl)-D-glucopyranose	KEGG COMPOUND
6-O-α-D-galactopyranosyl-D-glucopyranose	IUPAC
α-D-Gal-(1→6)-D-Glc	ChEBI
α-D-galactosyl-(1→6)-D-glucose	ChEBI
α-D-Galp-(1→6)-D-Glcp	ChEBI
D-Melibiose	ChemIDplus
D-mellibiose	ChEBI
Gal-α(1,6)Glc	ChEBI
Melibiose	KEGG COMPOUND
melibiose	UniProt
WURCS=2.0/2,2,1/[a2122h-1x_1-5][a2112h-1a_1-5]/1-2/a6-b1	GlyTouCan

Citations

Last Modified

07 April 2021