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

• ChemBase ID: 165881
• Molecular Formular: C21H20O7
• Molecular Mass: 384.3793
• Monoisotopic Mass: 384.12090298
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](CC2)(C(O)C)O)O)OC
• Canonical SMILES: COc1cccc2c1C(=O)c1c(O)c3CC[C@](Cc3c(c1C2=O)O)(O)C(O)C
• InChI: InChI=1S/C21H20O7/c1-9(22)21(27)7-6-10-12(8-21)19(25)15-16(17(10)23)20(26)14-11(18(15)24)4-3-5-13(14)28-2/h3-5,9,22-23,25,27H,6-8H2,1-2H3/t9?,21-/m1/s1
• InChIKey: FCGIQQFXNIJXMK-SSKGYDFUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8R)-6,8,11-trihydroxy-8-(1-hydroxyethyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC Traditional name: (8R)-6,8,11-trihydroxy-8-(1-hydroxyethyl)-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione
• Synonyms: (8R)-7,8,9,10-Tetrahydro-6,8,11-trihydroxy-8-(1-hydroxyethyl)-1-methoxy-5,12-naphthacenedione; 7-Deoxy Daunorubicinol Aglycone (Mixture of Diastereomers)

Database IDs

• CAS Number: 210837-87-9
• PubChem SID: 162260014
• PubChem CID: 10339969

CALCULATED PROPERTIES

• Acid pKa: 9.946949
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 3.169666
• LogD (pH = 7.4): 3.1684592
• Log P: 3.1696815
• Molar Refractivity: 101.3284 cm^3
• Polarizability: 38.50134 Å^3
• Polar Surface Area: 124.29 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D232620

A metabolite of Daunorubicin.

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)