(8S,10S)-8-acetyl-6,8,10,11-tetrahydroxy-1-(13C,2H3)methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase ID: 165424
• Molecular Formular: C21H18O8
• Molecular Mass: 399.35547484
• Monoisotopic Mass: 399.10352237
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](C[C@@H]2O)(C(=O)C)O)O)O[13CH3]
• Canonical SMILES: [13CH3]Oc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)[C@@H](O)C[C@](C2)(O)C(=O)C
• InChI: InChI=1S/C21H18O8/c1-8(22)21(28)6-10-13(11(23)7-21)19(26)16-15(18(10)25)17(24)9-4-3-5-12(29-2)14(9)20(16)27/h3-5,11,23,25-26,28H,6-7H2,1-2H3/t11-,21-/m0/s1/i2+1
• InChIKey: YOFDHOWPGULAQF-GLGRYMJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S,10S)-8-acetyl-6,8,10,11-tetrahydroxy-1-(^1^3C,^2H₃)methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC Traditional name: (8S,10S)-8-acetyl-6,8,10,11-tetrahydroxy-1-(^1^3C,^2H₃)methoxy-9,10-dihydro-7H-tetracene-5,12-dione
• Synonyms: (8S,10S)-8-Acetyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-(methoxy-13C,d3)- -5,12-naphthacenedione; (+)-Daunomycinone-13C,d3; Daunomycin-13C,d3 Aglicone; Daunomycinon-13C,d3; Daunorubicin-13C,d3 Aglycone; Daunorubicinone-13C,d3; Leukaemomycinone C-13C,d3; NSC 109351-13C,d3; Daunomycinone-13C,d3

Database IDs

• PubChem SID: 162259557
• PubChem CID: 46780564

CALCULATED PROPERTIES

• Acid pKa: 9.52904
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 2.2515504
• LogD (pH = 7.4): 2.2484004
• Log P: 2.2515907
• Molar Refractivity: 101.8751 cm^3
• Polarizability: 38.764942 Å^3
• Polar Surface Area: 141.36 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D193852

The main labelled metabolite of Daunorubicin (DNR).

REFERENCES

• Hjelle, J.T., et al.: J. Pharmacol. Exp. Therap., 229, 372 (1984)
• Prikrylova, V., et al.: J. Antibiotics, 38, 1714 (1984)