N-[(2S,3S,4S,6R)-6-{[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-(13C,2H3)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: 179053
• Molecular Formular: C29H28F3NO11
• Molecular Mass: 624.52058444
• Monoisotopic Mass: 624.16480022
• SMILES: c1cc(c2c(c1)C(=O)c1c(C2=O)c(c2c(c1O)C[C@@](C[C@@H]2O[C@H]1C[C@H]([C@@H]([C@@H](O1)C)O)NC(=O)C(F)(F)F)(O)C(=O)C)O)O[13CH3]
• Canonical SMILES: [13CH3]Oc1cccc2c1C(=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)C
• InChI: InChI=1S/C29H28F3NO11/c1-10-22(35)14(33-27(40)29(30,31)32)7-17(43-10)44-16-9-28(41,11(2)34)8-13-19(16)26(39)21-20(24(13)37)23(36)12-5-4-6-15(42-3)18(12)25(21)38/h4-6,10,14,16-17,22,35,37,39,41H,7-9H2,1-3H3,(H,33,40)/t10-,14-,16-,17-,22+,28-/m0/s1/i3+1
• InChIKey: VOASREXNXKOKBP-AVOARPDJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3S,4S,6R)-6-{[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-(^1^3C,^2H₃)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,6R)-6-{[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-(^1^3C,^2H₃)methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]-2,2,2-trifluoroacetamide
• Synonyms: (8S,10S)-8-Acetyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-10-[[2,3,6-trideoxy-3-[(2,2,2-trifluoroacetyl)amino]-α-L-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione-13CD3; N-(Trifluoroacetyl)daunorubicin-13CD3

Database IDs

• PubChem SID: 164234963
• PubChem CID: 71752751

CALCULATED PROPERTIES

• Acid pKa: 5.4414153
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): 2.9945219
• LogD (pH = 7.4): 2.3602633
• Log P: 3.2725966
• Molar Refractivity: 143.3455 cm^3
• Polarizability: 54.911163 Å^3
• Polar Surface Area: 188.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Red Solid

DETAILS

Toronto Research Chemicals - T786987

Protected Daunorubicin.

REFERENCES

• Duvvuri, M., et al.: Biochem., 44, 15743 (2005)
• Zhang, G., et al.: J. Med. Chem., 49, 1792 (2005)
• Zhang, G., et al.: Bioorg. Med. Chem., 14, 426 (2005)
• Cui, F., et al.: J., Pharm., Biomed., Anal., 48, 1029 (2008)