N-[(2S,3S,4S,6S)-6-{[(1S,3S)-3-{2-[(tert-butyldimethyl-λ4-sulfanyl)oxy]acetyl}-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]-2,2,2-trifluoroacetamide

• ChemBase ID: 179042
• Molecular Formular: C35H42F3NO12S
• Molecular Mass: 757.7676896
• Monoisotopic Mass: 757.23798145
• 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)COS(C(C)(C)C)(C)C)O)O)OC
• Canonical SMILES: COc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)[C@@H](O[C@H]1O[C@@H](C)[C@H]([C@@H](C1)NC(=O)C(F)(F)F)O)C[C@](C2)(O)C(=O)COS(C(C)(C)C)(C)C
• InChI: InChI=1S/C35H42F3NO12S/c1-15-27(41)18(39-32(46)35(36,37)38)11-22(50-15)51-20-13-34(47,21(40)14-49-52(6,7)33(2,3)4)12-17-24(20)31(45)26-25(29(17)43)28(42)16-9-8-10-19(48-5)23(16)30(26)44/h8-10,15,18,20,22,27,41,43,45,47H,11-14H2,1-7H3,(H,39,46)/t15-,18-,20-,22+,27+,34-/m0/s1
• InChIKey: VEQFJZMHMSPBRO-NBZIXRDRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3S,4S,6S)-6-{[(1S,3S)-3-{2-[(tert-butyldimethyl-λ^4-sulfanyl)oxy]acetyl}-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]-2,2,2-trifluoroacetamide
• IUPAC Traditional name: N-[(2S,3S,4S,6S)-6-{[(1S,3S)-3-{2-[(tert-butyldimethyl-λ^4-sulfanyl)oxy]acetyl}-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]-2,2,2-trifluoroacetamide
• Synonyms: N-Trifluoroacetyl-8-(2-tert-butyl(dimethyl)silyl]oxy)adriamycin; (1S,3S)-2,3,6-Trideoxy-3-(2,2,2-trifluoroacetamido)-3-ert-butyl(dimethyl)silylglycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl-α-L-lyxo-hexopyranoside; N-Trifluoroacetyl-8-(2-tert-butyl(dimethyl)silyl]oxy) Doxorubicin

Database IDs

• PubChem SID: 164234952
• PubChem CID: 71752750

CALCULATED PROPERTIES

• Acid pKa: 5.3934793
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): 3.3683805
• LogD (pH = 7.4): 2.5921686
• Log P: 3.6877
• Molar Refractivity: 180.6516 cm^3
• Polarizability: 70.31024 Å^3
• Polar Surface Area: 198.15 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Dark Red Crystals

DETAILS

Toronto Research Chemicals - T786760

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)