(8R)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase ID: 165919
• Molecular Formular: C21H18O8
• Molecular Mass: 398.36282
• Monoisotopic Mass: 398.10016754
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](CC2)(C(=O)CO)O)O)OC
• Canonical SMILES: COc1cccc2c1C(=O)c1c(O)c3CC[C@](Cc3c(c1C2=O)O)(O)C(=O)CO
• InChI: InChI=1S/C21H18O8/c1-29-12-4-2-3-10-14(12)20(27)16-15(18(10)25)19(26)11-7-21(28,13(23)8-22)6-5-9(11)17(16)24/h2-4,22,24,26,28H,5-8H2,1H3/t21-/m1/s1
• InChIKey: QHGFPRZWWKUHKF-OAQYLSRUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8R)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC Traditional name: (8R)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione
• Synonyms: (8R)-7,8,9,10-Tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione; 7-Deoxyadriamycin Aglycone; 7-Deoxyadriamycinone; 7-Deoxydoxorubicinone; 7-Deoxyepirubicin Aglycone; NSC 270536; 7-Deoxy Doxorubicin Aglycone (approxmately 75%)

Database IDs

• CAS Number: 38554-25-5
• PubChem SID: 162260052
• PubChem CID: 83958

CALCULATED PROPERTIES

• Acid pKa: 9.411919
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 2.737895
• LogD (pH = 7.4): 2.7337737
• Log P: 2.7379477
• Molar Refractivity: 102.1054 cm^3
• Polarizability: 38.767902 Å^3
• Polar Surface Area: 141.36 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Dark Red Solid

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D232910

A metabolite of Doxorubicin (Dx) (D558000).

REFERENCES

• Calvo, D., et al.: J. Biol. Chem., 268, 19929 (1993)
• Martens, F., et al.: Drugs, 62, 1463 (1993)
• Osgood, D., et al.: J. Clin. Endocrinol. Metabol., 88, 2869 (1993)
• Zhang, Y., et al.: J. Clin. Invest., 115, 2870 (1993)