aloin   Click here for help

GtoPdb Ligand ID: 12498

Synonyms: aloin A/B
Compound class: Natural product
Comment: Aloin is a mixture of stereoisomers, aloin A (barbaloin; 10S) and aloin B (isobarbaloin; 10R). We show the molecule without stereo specification at the 10 position to represent the mixture. It is a naturally ocurring compound that is present in Aloe species, that has laxative activity.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 7
Rotatable bonds 3
Topological polar surface area 167.91
Molecular weight 418.39
XLogP -2.14
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES C1=CC(=C2C(=C1)C(C3=CC(=CC(=C3C2=O)O)CO)[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)O
Isomeric SMILES C1=CC2=C(C(=C1)O)C(=O)C3=C(C2[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C=C(C=C3O)CO
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
InChI Key AFHJQYHRLPMKHU-CGISPIQUSA-N
Classification Click here for help
Compound class Natural product
IUPAC Name Click here for help
1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
Synonyms Click here for help
aloin A/B
Database Links Click here for help
Specialist databases
GPCRdb Ligand aloin
Other databases
BindingDB Ligand 50269016
ChEBI CHEBI:73222
ChEMBL Ligand CHEMBL497001
DrugBank Ligand DB15477
GtoPdb PubChem SID 479821288
PubChem CID 9866696
Search Google for chemical match using the InChIKey AFHJQYHRLPMKHU-CGISPIQUSA-N
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UniChem Compound Search for chemical match using the InChIKey AFHJQYHRLPMKHU-CGISPIQUSA-N
UniChem Connectivity Search for chemical match using the InChIKey AFHJQYHRLPMKHU-CGISPIQUSA-N