CHEBI:73222 - aloin

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ChEBI Name aloin
ChEBI ID CHEBI:73222
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Steve Jupe
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Formula C21H22O9
Net Charge 0
Average Mass 418.39400
Monoisotopic Mass 418.126
InChI InChI=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
InChIKey AFHJQYHRLPMKHU-CGISPIQUSA-N
SMILES [H][C@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1c2cccc(O)c2C(=O)c2c(O)cc(CO)cc12
Roles Classification
Biological Role(s): 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(s): 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.
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ChEBI Ontology
Outgoing 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 Sources
10-(1',5'-anhydroglucosyl)aloe-emodin-9-anthrone ChemIDplus
10-β-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)anthracen-9(10H)-one ChemIDplus
10-β-D-glucopyranosyl-1,8-dihydroxy-3-hydroxymethyl-9(10H)-anthrone ChemIDplus
Database Links Databases
Aloin Wikipedia
HMDB0035219 HMDB
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Registry Number Type Source
1443124 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12622939 PubMed citation Europe PMC
17269040 PubMed citation Europe PMC
20933355 PubMed citation Europe PMC
22139409 PubMed citation Europe PMC
22495441 PubMed citation Europe PMC
23569857 PubMed citation Europe PMC
Last Modified
14 June 2013