(2S,3S,4S,6S)-6-{[(1S,3S)-3-[2-(acetyloxy)acetyl]-3,5,12-trihydroxy-10-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: 179060
• Molecular Formular: C38H33F3N2O16
• Molecular Mass: 830.6676296
• Monoisotopic Mass: 830.17821765
• 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)OC(=O)c1ccc(cc1)[N+](=O)[O-])C)(C(=O)COC(=O)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)OC(=O)c1ccc(cc1)[N+](=O)[O-])C[C@](C2)(O)C(=O)COC(=O)C
• InChI: InChI=1S/C38H33F3N2O16/c1-15-34(59-35(50)17-7-9-18(10-8-17)43(53)54)21(42-36(51)38(39,40)41)11-25(57-15)58-23-13-37(52,24(45)14-56-16(2)44)12-20-27(23)33(49)29-28(31(20)47)30(46)19-5-4-6-22(55-3)26(19)32(29)48/h4-10,15,21,23,25,34,47,49,52H,11-14H2,1-3H3,(H,42,51)/t15-,21-,23-,25+,34+,37-/m0/s1
• InChIKey: HOSOPDUHHADMKV-HOSIRKRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,6S)-6-{[(1S,3S)-3-[2-(acetyloxy)acetyl]-3,5,12-trihydroxy-10-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,6S)-6-{[(1S,3S)-3-[2-(acetyloxy)acetyl]-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy}-2-methyl-4-(trifluoroacetamido)oxan-3-yl 4-nitrobenzoate
• Synonyms: N-Trifluoroacetyl-4’-nitobenzoate-8-(2-acetyloxy)adriamycin; N-Trifluoroacetyl-4'-nitobenzoate-8-(2-acetyloxy) Doxorubicin

Database IDs

• PubChem SID: 164234970
• PubChem CID: 71752753

CALCULATED PROPERTIES

• Acid pKa: 5.232824
• H Acceptors: 14
• H Donor: 4
• LogD (pH = 5.5): 4.959996
• LogD (pH = 7.4): 4.4059644
• Log P: 5.331758
• Molar Refractivity: 191.3459 cm^3
• Polarizability: 72.95569 Å^3
• Polar Surface Area: 267.11 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Red Solid

DETAILS

Toronto Research Chemicals - T787280

Doxorubicin (D558000) derivative.