(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}-2-methyl-4-(trifluoroacetamido)oxan-3-yl 4-nitrobenzoate

• ChemBase ID: 179028
• Molecular Formular: C36H31F3N2O14
• Molecular Mass: 773.62420444
• Monoisotopic Mass: 773.17609318
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](C[C@@H]2O[C@@H]1O[C@H]([C@@H](OC(=O)c2ccc(cc2)[N+](=O)[O-])[C@H](NC(=O)C(F)(F)F)C1)C)(C(=O)C)O)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)OC(=O)c1ccc(cc1)[N+](=O)[O-])C[C@](C2)(O)C(=O)C
• InChI: InChI=1S/C36H31F3N2O14/c1-14-32(55-33(47)16-7-9-17(10-8-16)41(50)51)20(40-34(48)36(37,38)39)11-23(53-14)54-22-13-35(49,15(2)42)12-19-25(22)31(46)27-26(29(19)44)28(43)18-5-4-6-21(52-3)24(18)30(27)45/h4-10,14,20,22-23,32,44,46,49H,11-13H2,1-3H3,(H,40,48)/t14-,20-,22-,23-,32+,35-/m0/s1/i3+1
• InChIKey: HGBZBLPEFVMINN-YJCBQRARSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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}-2-methyl-4-(trifluoroacetamido)oxan-3-yl 4-nitrobenzoate
• IUPAC Traditional name: (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}-2-methyl-4-(trifluoroacetamido)oxan-3-yl 4-nitrobenzoate
• Synonyms: (8S-cis)-8-Acetyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-10-[[2,3,6-trideoxy-4-O-(4-nitrobenzoyl)-3-[(trifluoroacetyl)amino]-α-L-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione-13CD3; N-Trifluoroacetamido-4'-p-nitrobenzoyl Daunorubicin-13CD3

Database IDs

• PubChem SID: 164234938
• PubChem CID: 71752744

CALCULATED PROPERTIES

• Acid pKa: 5.265443
• H Acceptors: 13
• H Donor: 4
• LogD (pH = 5.5): 5.3515034
• LogD (pH = 7.4): 4.7837954
• Log P: 5.7078805
• Molar Refractivity: 180.4922 cm^3
• Polarizability: 68.39914 Å^3
• Polar Surface Area: 240.81 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Dark Red Solid

DETAILS

Toronto Research Chemicals - T783062

Intermediate in the production of labelled Daunorubicin.

REFERENCES

• Acton, E., et al.: J. Med. Chem., 17, 659 (1974)