(1R,2S,3S,5S)-3-(4-chlorophenyl)-8-(2H3)methyl-2-[3-(4-methylphenyl)-1,2-oxazol-5-yl]-8-azabicyclo[3.2.1]octane hydrochloride

• ChemBase ID: 177649
• Molecular Formular: C24H26Cl2N2O
• Molecular Mass: 429.38204
• Monoisotopic Mass: 428.14221882
• SMILES: Cl.[C@@H]12CC[C@@H](N1C)[C@H]([C@H](C2)c1ccc(cc1)Cl)c1cc(no1)c1ccc(cc1)C
• Canonical SMILES: Cc1ccc(cc1)c1noc(c1)[C@@H]1[C@H]2CC[C@H](N2C)C[C@@H]1c1ccc(cc1)Cl.Cl
• InChI: InChI=1S/C24H25ClN2O.ClH/c1-15-3-5-17(6-4-15)21-14-23(28-26-21)24-20(16-7-9-18(25)10-8-16)13-19-11-12-22(24)27(19)2;/h3-10,14,19-20,22,24H,11-13H2,1-2H3;1H/t19-,20+,22+,24-;/m0./s1
• InChIKey: IZMZEMAKFSYLMD-SXBQIKTFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3S,5S)-3-(4-chlorophenyl)-8-(^2H₃)methyl-2-[3-(4-methylphenyl)-1,2-oxazol-5-yl]-8-azabicyclo[3.2.1]octane hydrochloride
• IUPAC Traditional name: (1R,2S,3S,5S)-3-(4-chlorophenyl)-8-(^2H₃)methyl-2-[3-(4-methylphenyl)-1,2-oxazol-5-yl]-8-azabicyclo[3.2.1]octane hydrochloride
• Synonyms: (3S)-3,4-Dihydro-8-methoxy-3-methylbenz[a]anthracene-1,7,12(2H)-trione; (+)-Rubiginone B2; Rubiginone B2

Database IDs

• CAS Number: 130548-10-6
• PubChem SID: 164233559
• PubChem CID: 71752137

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.4085183
• LogD (pH = 7.4): 3.6527843
• Log P: 5.806205
• Molar Refractivity: 114.2066 cm^3
• Polarizability: 45.146076 Å^3
• Polar Surface Area: 29.27 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Pale Yellow Solid

DETAILS

Toronto Research Chemicals - R701300

Antibiotic with vincristine-cytotoxicity potentiating activity.

REFERENCES

• Oka, M., et al.: J. Antibiot., 43, 967 (1990)
• Rix, U., et al.: ChemBioChem., 6, 838 (2005).