(5Z)-3-Benzyl-5-(3-trifluoromethylbenzylidene)furan-2(5H)-one

ID: ALA2228181

PubChem CID: 24861990

Max Phase: Preclinical

Molecular Formula: C19H13F3O2

Molecular Weight: 330.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1O/C(=C\c2cccc(C(F)(F)F)c2)C=C1Cc1ccccc1

Standard InChI:  InChI=1S/C19H13F3O2/c20-19(21,22)16-8-4-7-14(10-16)11-17-12-15(18(23)24-17)9-13-5-2-1-3-6-13/h1-8,10-12H,9H2/b17-11-

Standard InChI Key:  SWIGUBIHDGIANX-BOPFTXTBSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    4.2883  -19.7837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260  -20.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9664  -19.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2220  -19.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0368  -19.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250  -21.0802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7478  -18.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4549  -19.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1622  -18.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8693  -19.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8654  -19.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1586  -20.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4515  -19.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2609  -20.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5523  -19.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8469  -20.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1363  -19.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311  -18.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8365  -18.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5471  -18.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1561  -21.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4471  -21.4635    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625  -21.4679    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.1496  -21.8702    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  1  5  1  0
  2  6  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
  5  7  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
  3 14  1  0
 12 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2228181

   (5Z)-3-benzyl-5-[[3-(trifluoromethyl)phenyl]methylidene]furan-2-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: 330.31

Molecular Weight (Monoisotopic): 330.0868

AlogP: 4.77

#Rotatable Bonds: 3

Polar Surface Area: 26.30

Molecular Species: ┄

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.21

CX LogD: 5.21

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.76

Np Likeness Score: 0.08

References

1. Teixeira RR, Barbosa LC, Forlani G, Piló-Veloso D, Walkimar de Mesquita Carneiro J..  (2008)  Synthesis of photosynthesis-inhibiting nostoclide analogues.,  56  (7): [PMID:18338868] [10.1021/jf072964g]

2. Teixeira RR, Pinheiro PF, Barbosa LC, Carneiro JW, Forlani G..  (2010)  QSAR modeling of photosynthesis-inhibiting nostoclide derivatives.,  66  (2): [PMID:19798697] [10.1002/ps.1855]

Source

Source(1):

• Scientific Literature