(10R)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracen-9-one

• ChemBase ID: 125705
• Molecular Formular: C21H22O9
• Molecular Mass: 418.39398
• Monoisotopic Mass: 418.12638228
• SMILES: O=C1c2c(cc(cc2O)CO)[C@@H](c2cccc(O)c12)[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO
• Canonical SMILES: OCc1cc(O)c2c(c1)[C@H]([C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)c1c(C2=O)c(O)ccc1
• 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-WEZNYRQKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10R)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracen-9-one
• IUPAC Traditional name: aloin
• Synonyms: Aloin

Database IDs

• CAS Number: 8015-61-0
• PubChem SID: 162220055
• PubChem CID: 313325; 14989
• CHEMBL: 497001
• Chemspider ID: 14269
• Unique Ingredient Identifier: W41H6S09F4
• Wikipedia Title: Aloin

CALCULATED PROPERTIES

• Acid pKa: 9.505504
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): 0.41494715
• LogD (pH = 7.4): 0.4116161
• Log P: 0.41498974
• Molar Refractivity: 103.7931 cm^3
• Polarizability: 40.31564 Å^3
• Polar Surface Area: 167.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 148°C (298.4°F) (70–80 °C for monohydrate)

Pharmacology Properties

• Admin Routes: Oral