CHEBI:16634 - raffinose

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name raffinose
ChEBI ID CHEBI:16634
Definition A trisaccharide composed of α-D-galactopyranose, α-D-glucopyranose and β-D-fructofuranose joined in sequence by 1→6 and 1↔2 glycosidic linkages, respectively.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:26521, CHEBI:49843, CHEBI:15015, CHEBI:8771
Supplier Information ChemicalBook:CB71310372, eMolecules:31254558, ZINC000001529505
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Raffinose is a trisaccharide composed of galactose, glucose, and fructose. It can be found in beans, cabbage, brussels sprouts, broccoli, asparagus, other vegetables, and whole grains. Raffinose can be hydrolyzed to D-galactose and sucrose by the enzyme α-galactosidase (α-GAL), an enzyme synthesized by bacteria found in the large intestine. α-GAL also hydrolyzes other α-galactosides such as stachyose, verbascose, and galactinol, if present. In plants, raffinose plays a significant role in stress responses, particularly temperature sensitivity, seed vigour, resistance to pathogens, and desiccation.
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Formula C18H32O16
Net Charge 0
Average Mass 504.43710
Monoisotopic Mass 504.16903
InChI InChI=1S/C18H32O16/c19-1-5-8(22)11(25)13(27)16(31-5)30-3-7-9(23)12(26)14(28)17(32-7)34-18(4-21)15(29)10(24)6(2-20)33-18/h5-17,19-29H,1-4H2/t5-,6-,7-,8+,9-,10-,11+,12+,13-,14-,15+,16+,17-,18+/m1/s1
InChIKey MUPFEKGTMRGPLJ-ZQSKZDJDSA-N
SMILES OC[C@H]1O[C@H](OC[C@H]2O[C@H](O[C@]3(CO)O[C@H](CO)[C@@H](O)[C@@H]3O)[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
Roles Classification
Biological Role(s): Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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ChEBI Ontology
Outgoing raffinose (CHEBI:16634) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
raffinose (CHEBI:16634) has role mouse metabolite (CHEBI:75771)
raffinose (CHEBI:16634) has role plant metabolite (CHEBI:76924)
raffinose (CHEBI:16634) is a raffinose family oligosaccharide (CHEBI:74961)
raffinose (CHEBI:16634) is a trisaccharide (CHEBI:27150)
Incoming 1F-α-D-galactosylraffinose (CHEBI:27603) has functional parent raffinose (CHEBI:16634)
stachyose (CHEBI:17164) has functional parent raffinose (CHEBI:16634)
IUPAC Name
β-D-fructofuranosyl α-D-galactopyranosyl-(1→6)-α-D-glucopyranoside
Synonyms Sources
6G-alpha-D-galactosylsucrose KEGG COMPOUND
α-D-galactopyranosyl-(1→6)-α-D-glucopyranosyl β-D-fructofuranoside JCBN
α-D-Galp-(1→6)-α-D-Glcp-(1↔2)-β-D-Fruf JCBN
Gossypose KEGG COMPOUND
Melitose KEGG COMPOUND
Melitriose KEGG COMPOUND
Raffinose KEGG COMPOUND
raffinose UniProt
rafinose ChEBI
raflinose ChEBI
Manual Xrefs Databases
C00001145 KNApSAcK
C00492 KEGG COMPOUND
CPD-1099 MetaCyc
G00249 KEGG GLYCAN
HMDB0003213 HMDB
RAF PDBeChem
Raffinose Wikipedia
View more database links
Registry Numbers Types Sources
512-69-6 CAS Registry Number KEGG COMPOUND
512-69-6 CAS Registry Number ChemIDplus
99543 Reaxys Registry Number Reaxys
Citations Types Sources
23317449 PubMed citation Europe PMC
23879777 PubMed citation Europe PMC
23882273 PubMed citation Europe PMC
24001862 PubMed citation Europe PMC
24354450 PubMed citation Europe PMC
24360500 PubMed citation Europe PMC
Last Modified
27 January 2016