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CHEBI:73222 - aloin

ChEBI IDCHEBI:73222
ChEBI Namealoin
Stars
DefinitionA diastereoisomeric mixture of aloin A (barbaloin) and aloin B (isobarbaloin), which have similar properties. It is a bitter-tasting, yellow-brown colored compound found in the exudate of at least 68 Aloe species at levels of up to 6.6% of leaf dry weight (making between 3% and 35% of the total exudate), and in another 17 species at indeterminate levels. It is used as a stimulant-laxative, treating constipation by inducing bowel movements.
Last Modified14 June 2013
Submittersjupe
DownloadsMolfile
FormulaC21H22O9
Net Charge0
Average Mass418.398
Monoisotopic Mass418.12638
SMILES[H][C@@]1(C2c3cccc(O)c3C(=O)c3c(O)cc(CO)cc32)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChIInChI=1S/C21H22O9/c22-6-8-4-10-14(21-20(29)19(28)17(26)13(7-23)30-21)9-2-1-3-11(24)15(9)18(27)16(10)12(25)5-8/h1-5,13-14,17,19-26,28-29H,6-7H2/t13-,14?,17-,19+,20-,21+/m1/s1
InChIKeyAFHJQYHRLPMKHU-CGISPIQUSA-N
Wikipedia
Roles Classification
Biological Role:
EC 1.14.18.1 (tyrosinase) inhibitor  Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.
Application:
laxative  An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.
ChEBI Ontology
Outgoing Relation(s)
aloin (CHEBI:73222) has part aloin A (CHEBI:2991)
aloin (CHEBI:73222) has part aloin B (CHEBI:74131)
aloin (CHEBI:73222) has role EC 1.14.18.1 (tyrosinase) inhibitor (CHEBI:59997)
aloin (CHEBI:73222) has role laxative (CHEBI:50503)
aloin (CHEBI:73222) is a diastereoisomeric mixture (CHEBI:60915)
IUPAC Name 
(1S)-1,5-anhydro-1-[4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]-D-glucitol
Synonyms  Source
10-(1',5'-anhydroglucosyl)aloe-emodin-9-anthroneChemIDplus
10-β-D-glucopyranosyl-1,8-dihydroxy-3-hydroxymethyl-9(10H)-anthroneChemIDplus
10-β-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)anthracen-9(10H)-oneChemIDplus
Manual XrefsDatabases
HMDB0035219HMDB
AloinWikipedia
Registry NumbersSources
Reaxys:1443124Reaxys
Citations