1,8-dihydroxy-3-(hydroxymethyl)-9,10-dihydro(2H5)anthracene-9,10-dione

• ChemBase ID: 159713
• Molecular Formular: C15H10O5
• Molecular Mass: 270.2369
• Monoisotopic Mass: 270.05282342
• SMILES: c1(cccc2c1C(=O)c1c(C2=O)cc(cc1O)CO)O
• Canonical SMILES: OCc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)ccc1
• InChI: InChI=1S/C15H10O5/c16-6-7-4-9-13(11(18)5-7)15(20)12-8(14(9)19)2-1-3-10(12)17/h1-5,16-18H,6H2
• InChIKey: YDQWDHRMZQUTBA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,8-dihydroxy-3-(hydroxymethyl)-9,10-dihydro(^2H₅)anthracene-9,10-dione
• IUPAC Traditional name: 1,8-dihydroxy-3-(hydroxymethyl)(^2H₅)anthracene-9,10-dione
• Synonyms: 1,8-Dihydroxy-3-(hydroxymethyl)-9,10-anthracenedione-d5; 1,8-Dihydroxy-3-(hydroxymethyl)anthraquinone-d5; 3-Hydroxymethylchrysazin-d5; 3-Hydroxymethylchrysazine-d5; Aloe-emodol-d5; NSC 38628-d5; Rhabarberone-d5; Aloe-emodin-d5

Database IDs

• PubChem SID: 162253848
• PubChem CID: 71313110

CALCULATED PROPERTIES

• Acid pKa: 9.00087
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.8440897
• LogD (pH = 7.4): 2.833502
• Log P: 2.8442256
• Molar Refractivity: 71.9287 cm^3
• Polarizability: 27.031057 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A575402

Shows significant inhibitory activity against the P-388 leukemia in mice when administered as a suspension in acetone-Tween 80. Has a specific in vitro and in vivo antineuroectodermal tumor activity. Cathartic.

REFERENCES

• Hung, K., et al.: J. Exp. Med., 188, 2357 (1998)
• Gazzola, P.T., et al.: Cancer Res., 60, 2800 (1998)
• Irie, T., et al.: Int. J. Cancer, 121, 8784 (1998)
• Zhao, J., et al.: Eur. J. Neurol., 14, 510 (1998)