1,6-dihydroxy-3-methyl-8-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione

• ChemBase ID: 167984
• Molecular Formular: C21H20O10
• Molecular Mass: 432.3775
• Monoisotopic Mass: 432.10564684
• SMILES: c1(cc(cc2c1C(=O)c1c(C2=O)cc(cc1O)C)O)O[C@@H]1OC([C@H]([C@@H](C1O)O)O)CO
• Canonical SMILES: OCC1O[C@@H](Oc2cc(O)cc3c2C(=O)c2c(C3=O)cc(cc2O)C)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H20O10/c1-7-2-9-14(11(24)3-7)18(27)15-10(16(9)25)4-8(23)5-12(15)30-21-20(29)19(28)17(26)13(6-22)31-21/h2-5,13,17,19-24,26,28-29H,6H2,1H3/t13?,17-,19+,20?,21-/m1/s1
• InChIKey: HSWIRQIYASIOBE-QZNXSETBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,6-dihydroxy-3-methyl-8-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione
• IUPAC Traditional name: 1,6-dihydroxy-3-methyl-8-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracene-9,10-dione
• Synonyms: 1-(β-D-Glucopyranosyloxy)-3,8-dihydroxy-6-methyl-9,10-anthracenedione; 3,8-Dihydroxy-6-methyl-1-anthraquinonyl β-D-Glucopyranoside; 8-O-β-D-Glucopyranosyl Emodin; Anthraglycoside B; Emodin 8-O-β-D-Glucopyranoside; Emodin 8-O-β-D-Glucoside; Emodin 8-β-D-Glucopyranoside; Emodin Glucoside B; NSC 257449; Emodin 8-β-D-Glucoside

Database IDs

• CAS Number: 23313-21-5
• PubChem SID: 162262116
• PubChem CID: 71316320

CALCULATED PROPERTIES

• Acid pKa: 7.278786
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): 0.896249
• LogD (pH = 7.4): 0.5400528
• Log P: 0.9033634
• Molar Refractivity: 104.2793 cm^3
• Polarizability: 40.653427 Å^3
• Polar Surface Area: 173.98 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E523010

A glucoside metabolite of Emodin (E523000).

REFERENCES

• Pan, X., et al.: Biochem. Eng. J., 5, 173 (2000)
• Srinivas, G., et al.: Eur. J. Pharmacol., 473, 117 (2000)
• Xiang, H., et al.: Chin. Pharm. J., 40, 96 (2000)
• Mokhtarani, B., et al.: Biochem. Eng. J., 38, 241 (2000)