2-oxo-2-[(2S,4S)-2,4,5,12-tetrahydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl acetate

• ChemBase ID: 159097
• Molecular Formular: C23H20O10
• Molecular Mass: 456.3989
• Monoisotopic Mass: 456.10564684
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](C[C@@H]2O)(C(=O)COC(=O)C)O)O)OC
• Canonical SMILES: COc1cccc2c1C(=O)c1c(O)c3[C@@H](O)C[C@](Cc3c(c1C2=O)O)(O)C(=O)COC(=O)C
• InChI: InChI=1S/C23H20O10/c1-9(24)33-8-14(26)23(31)6-11-15(12(25)7-23)21(29)18-17(20(11)28)19(27)10-4-3-5-13(32-2)16(10)22(18)30/h3-5,12,25,28-29,31H,6-8H2,1-2H3/t12-,23-/m0/s1
• InChIKey: HKNGLRVIYRYQHU-MYODQAERSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-oxo-2-[(2S,4S)-2,4,5,12-tetrahydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl acetate
• IUPAC Traditional name: 2-oxo-2-[(2S,4S)-2,4,5,12-tetrahydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]ethyl acetate
• Synonyms: 14-O-Acetyladriamycinone; (8S,10S)-8-[2-(Acetyloxy)acetyl]-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-5,12-naphthacenedione; (8S,cis)-8-[2-(Acetyloxy)acetyl]-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-5,12-naphthacenedione; 14-O-Acetyldaunomycinone

Database IDs

• CAS Number: 29984-41-6
• PubChem SID: 162253232
• PubChem CID: 11166981

CALCULATED PROPERTIES

• Acid pKa: 9.528966
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 1.8754278
• LogD (pH = 7.4): 1.8722773
• Log P: 1.8754681
• Molar Refractivity: 112.7288 cm^3
• Polarizability: 43.29164 Å^3
• Polar Surface Area: 167.66 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Dark Red Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A172170

Protected Daunomycinone (D193850), the main 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 (1985)