8,12-Dimethyl-3-(4-trifluoromethyl-phenyl)-4,9,10,11-tetraoxa-tricyclo[6.2.2.0*1,6*]dodec-6-en-5-one

ID: ALA2435060

PubChem CID: 73346346

Max Phase: Preclinical

Molecular Formula: C17H15F3O5

Molecular Weight: 356.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1O[C@]23CC(c4ccc(C(F)(F)F)cc4)OC(=O)C2=C[C@@]1(C)OO3

Standard InChI:  InChI=1S/C17H15F3O5/c1-9-15(2)7-12-14(21)22-13(8-16(12,23-9)25-24-15)10-3-5-11(6-4-10)17(18,19)20/h3-7,9,13H,8H2,1-2H3/t9?,13?,15-,16+/m1/s1

Standard InChI Key:  ZHHRIFKTPFTONY-KWQPOOPASA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    4.3697  -11.9905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072  -11.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072  -10.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3697  -10.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1433  -10.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7259  -11.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8476  -11.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7361  -10.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6322  -11.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6333  -10.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8988  -10.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1587  -10.7103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1576  -11.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8966  -11.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9011   -9.4662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4451  -11.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349  -11.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0237  -11.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213  -12.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7362  -13.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4444  -12.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6947  -13.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4003  -12.7907    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6939  -14.0225    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4052  -13.6046    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 10  4  2  0
  9  1  1  6
  1  2  1  0
  2  3  1  0
  3  4  1  0
  9  5  1  0
  5  6  1  0
  3  6  1  0
  2  7  1  0
  3  8  1  1
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11 15  2  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 13 16  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2435060

   (1S,8R)-8,12-dimethyl-3-[4-(trifluoromethyl)phenyl]-4,9,10,11-tetraoxatricyclo[6.2.2.01,6]dodec-6-en-5-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 356.30

Molecular Weight (Monoisotopic): 356.0872

AlogP: 3.46

#Rotatable Bonds: 1

Polar Surface Area: 53.99

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.34

CX LogD: 4.34

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.57

Np Likeness Score: 1.13

References

1. Hossain MI, Świtalska M, Peng W, Takashima M, Wang N, Kaiser M, Wietrzyk J, Dan S, Yamori T, Inokuchi T..  (2013)  Design, synthesis, and in vitro cancer cell growth inhibition evaluation and antimalarial testing of trioxanes installed in cyclic 2-enoate substructures.,  69  [PMID:24056020] [10.1016/j.ejmech.2013.08.008]

Source

Source(1):

• Scientific Literature