(8R)-8-(1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-(13C,2H3)methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase ID: 165915
• Molecular Formular: C21H20O8
• Molecular Mass: 401.37135484
• Monoisotopic Mass: 401.11917244
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](CC2)(C(O)CO)O)O)O[13CH3]
• Canonical SMILES: [13CH3]Oc1cccc2c1C(=O)c1c(O)c3CC[C@](Cc3c(c1C2=O)O)(O)C(CO)O
• InChI: InChI=1S/C21H20O8/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/h2-4,13,22-24,26,28H,5-8H2,1H3/t13?,21-/m1/s1/i1+1
• InChIKey: IGJIPNOEJDYNRR-KZQUSOCQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8R)-8-(1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-(^1^3C,^2H₃)methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC Traditional name: (8R)-8-(1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-(^1^3C,^2H₃)methoxy-9,10-dihydro-7H-tetracene-5,12-dione
• Synonyms: (8R)-8-(1,2-Dihydroxyethyl)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione-13C,d3; 7-Deoxy Doxorubicinol Aglycone-13C,d3 (Mixture of Diastereomers)

Database IDs

• PubChem SID: 162260048
• PubChem CID: 71315450

CALCULATED PROPERTIES

• Acid pKa: 9.946417
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 2.1227562
• LogD (pH = 7.4): 2.1215477
• Log P: 2.1227715
• Molar Refractivity: 102.8721 cm^3
• Polarizability: 39.16506 Å^3
• Polar Surface Area: 144.52 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D232899

A labelled metabolite of Doxorubicin.

REFERENCES

• Acton, E.M., et al.: J. Med. Chem., 17, 659 (1974)
• Richter, I., et al.: Phytochemistry, 15, 67 (1974)