2,2,2-trifluoro-N-[(2S,3S,4S,6S)-3-hydroxy-2-methyl-6-{[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-4-yl]acetamide

• ChemBase ID: 179054
• Molecular Formular: C29H28F3NO12
• Molecular Mass: 639.5273296
• Monoisotopic Mass: 639.15636
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](C[C@@H]2O[C@H]1O[C@H]([C@H]([C@@H](C1)NC(=O)C(F)(F)F)O)C)(C(=O)CO)O)O)OC
• Canonical SMILES: OCC(=O)[C@@]1(O)C[C@H](O[C@H]2O[C@@H](C)[C@H]([C@@H](C2)NC(=O)C(F)(F)F)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC
• InChI: InChI=1S/C29H28F3NO12/c1-10-22(36)13(33-27(41)29(30,31)32)6-17(44-10)45-15-8-28(42,16(35)9-34)7-12-19(15)26(40)21-20(24(12)38)23(37)11-4-3-5-14(43-2)18(11)25(21)39/h3-5,10,13,15,17,22,34,36,38,40,42H,6-9H2,1-2H3,(H,33,41)/t10-,13-,15-,17+,22+,28-/m0/s1
• InChIKey: RQIOYWADAKTIJC-BRHGRERGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2,2-trifluoro-N-[(2S,3S,4S,6S)-3-hydroxy-2-methyl-6-{[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-4-yl]acetamide
• IUPAC Traditional name: 2,2,2-trifluoro-N-[(2S,3S,4S,6S)-3-hydroxy-2-methyl-6-{[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy}oxan-4-yl]acetamide
• Synonyms: N-Trifluoroacetyladriamycin; NSC 283464; (8S-cis)-7,8,9,10-Tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-10-[[2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-α-L-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione; (1S,3S)- α-2,3,6-trideoxy-3-(2,2,2-trifluoroacetamido)-3-glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl L-lyxo-Hexopyranoside; N-Trifluoroacetyldoxorubicin

Database IDs

• CAS Number: 26295-56-7
• PubChem SID: 164234964
• PubChem CID: 71752752

CALCULATED PROPERTIES

• Acid pKa: 5.3934793
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): 2.156845
• LogD (pH = 7.4): 1.539444
• Log P: 2.4553485
• Molar Refractivity: 145.0477 cm^3
• Polarizability: 55.614723 Å^3
• Polar Surface Area: 209.15 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Red Solid

DETAILS

Toronto Research Chemicals - T786995

Doxorubicin (D558000) metabolite. Cytotoxic interaction with DNA.

REFERENCES

• Potmesil, M. et al.: Eur. J. Cancer Clin. On. 19, 109 (1983)
• Bodley, A., et al.: Cancer Res. 49, 5969 (1989)