(8S,10S)-1,6,8,10,11-pentahydroxy-8-(2-hydroxyacetyl)-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase ID: 166554
• Molecular Formular: C20H16O9
• Molecular Mass: 400.33564
• Monoisotopic Mass: 400.07943209
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](C[C@@H]2O)(C(=O)CO)O)O)O
• Canonical SMILES: OCC(=O)[C@@]1(O)C[C@H](O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2O
• InChI: InChI=1S/C20H16O9/c21-6-11(24)20(29)4-8-13(10(23)5-20)19(28)15-14(17(8)26)16(25)7-2-1-3-9(22)12(7)18(15)27/h1-3,10,21-23,26,28-29H,4-6H2/t10-,20-/m0/s1
• InChIKey: WLRQJZRSYGQUKG-FVINQWEUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S,10S)-1,6,8,10,11-pentahydroxy-8-(2-hydroxyacetyl)-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC Traditional name: (8S,10S)-1,6,8,10,11-pentahydroxy-8-(2-hydroxyacetyl)-9,10-dihydro-7H-tetracene-5,12-dione
• Synonyms: (8S-cis)-7,8,9,10-Tetrahydro-1,6,8,10,11-pentahydroxy-8-(hydroxyacetyl)-5,12-naphthacenedione; (8S,10S)-7,8,9,10-Tetrahydro-1,6,8,10,11-pentahydroxy-8-(hydroxyacetyl)-5,12-naphthacenedione; 4-O-Desmethyldoxorubicinone

Database IDs

• CAS Number: 65446-19-7
• PubChem SID: 162260687
• PubChem CID: 71315773

CALCULATED PROPERTIES

• Acid pKa: 9.144913
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): 1.938351
• LogD (pH = 7.4): 1.930733
• Log P: 1.9384487
• Molar Refractivity: 99.095 cm^3
• Polarizability: 37.545033 Å^3
• Polar Surface Area: 172.59 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Red Solid

DETAILS

Toronto Research Chemicals - D292570

Doxorubicinone (D559070) analogs.

REFERENCES

• Chan, K. et al.: J. Pharm. Sci. 67, 1748 (1978)