(8S,10S)-8-acetyl-1,6,8,10,11-pentahydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase ID: 165752
• Molecular Formular: C20H16O8
• Molecular Mass: 384.33624
• Monoisotopic Mass: 384.08451747
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](C[C@@H]2O)(C(=O)C)O)O)O
• Canonical SMILES: O[C@H]1C[C@@](O)(Cc2c1c(O)c1c(c2O)C(=O)c2c(C1=O)c(O)ccc2)C(=O)C
• InChI: InChI=1S/C20H16O8/c1-7(21)20(28)5-9-13(11(23)6-20)19(27)15-14(17(9)25)16(24)8-3-2-4-10(22)12(8)18(15)26/h2-4,11,22-23,25,27-28H,5-6H2,1H3/t11-,20-/m0/s1
• InChIKey: XYDJGVROLWFENK-YBTHPKLGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S,10S)-8-acetyl-1,6,8,10,11-pentahydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC Traditional name: (8S,10S)-8-acetyl-1,6,8,10,11-pentahydroxy-9,10-dihydro-7H-tetracene-5,12-dione
• Synonyms: (8S,10S)-8-Acetyl-7,8,9,10-tetrahydro-1,6,8,10,11-pentahydroxy-5,12-naphthacenedione; (+)-Carminomycinone; 4-Demethoxy-4-hydroxydaunomycinone; 4-O-Demethyldaunomycinone; Carminomycinone; 4-Demethyl Daunomycinone

Database IDs

• CAS Number: 52744-22-6
• PubChem SID: 162259885
• PubChem CID: 171197

CALCULATED PROPERTIES

• Acid pKa: 9.144952
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 2.755599
• LogD (pH = 7.4): 2.7479818
• Log P: 2.7556968
• Molar Refractivity: 97.3928 cm^3
• Polarizability: 36.868816 Å^3
• Polar Surface Area: 152.36 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Red Solid
• Melting Point: >240°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D230900

A metabolite Daunorubicin in liver microsomes.

REFERENCES

• Ogawa, Y., et al.: J. Antibiotics, 37, 44 (1984)
• Schwartz, H.S., et al.: Cancer Res., 44, 2480 (1984)
• Burke, T.G., et al.: Biochemistry, 24, 1768 (1984)