2-[(1r,3r,5r,7r)-dispiro[adamantane-2,2'-[1,3,4,6]tetraoxane-5',1''-cyclohexane]-4''-yl]acetic acid

• ChemBase ID: 174849
• Molecular Formular: C18H26O6
• Molecular Mass: 338.39544
• Monoisotopic Mass: 338.17293855
• SMILES: [C@@H]12C[C@H]3C[C@@H](C1)C1([C@@H](C2)C3)OOC2(OO1)CCC(CC2)CC(=O)O
• Canonical SMILES: OC(=O)CC1CCC2(CC1)OOC1(OO2)[C@@H]2C[C@@H]3C[C@H]1C[C@H](C2)C3
• InChI: InChI=1S/C18H26O6/c19-16(20)10-11-1-3-17(4-2-11)21-23-18(24-22-17)14-6-12-5-13(8-14)9-15(18)7-12/h11-15H,1-10H2,(H,19,20)/t11?,12-,13+,14-,15+,17?,18?
• InChIKey: KXOXRSVQUACCHR-MMWAZMRTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1r,3r,5r,7r)-dispiro[adamantane-2,2'-[1,3,4,6]tetraoxane-5',1''-cyclohexane]-4''-yl]acetic acid
• IUPAC Traditional name: (1r,3r,5r,7r)-dispiro[adamantane-2,2'-[1,3,4,6]tetraoxane-5',1''-cyclohexane]-4''-ylacetic acid
• Synonyms: Dispiro[cyclohexane-1,3'-[1,2,4,5]tetroxane-6',2''-tricyclo[3.3.1.13,7]decane]-4-acetic Acid; MT04

Database IDs

• CAS Number: 923267-23-6
• PubChem SID: 164230759
• PubChem CID: 15946778

CALCULATED PROPERTIES

• Acid pKa: 3.8000553
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.2733967
• LogD (pH = 7.4): 0.7131817
• Log P: 3.9755387
• Molar Refractivity: 82.2102 cm^3
• Polarizability: 33.627724 Å^3
• Polar Surface Area: 74.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M755500

MT04 is an analogue of the fasciocidal drug candidate OZ78, a 1,2,4-trioxolane. MT04 was tested as a potential novel fasciocidal drug against Fasciola hepatica and Echinostoma caproni.

REFERENCES

• Keiser, J., et al.: J. Antimicrob. Chemother., 58, 1193 (2006)
• Keiser, J., et al.: Exp. Parasitol., 119, 87 (2006)
• Dong, Y., et al.: J. Med. Chem., 53, 481 (2006)
• Duthaler, U., et al.: Antimicrob. Agents Chemother., 54, 4596 (2006)