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

ID: ALA2228182

PubChem CID: 24861991

Max Phase: Preclinical

Molecular Formula: C19H13F3O2

Molecular Weight: 330.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1O/C(=C\c2ccccc2C(F)(F)F)C=C1Cc1ccccc1

Standard InChI:  InChI=1S/C19H13F3O2/c20-19(21,22)17-9-5-4-8-14(17)11-16-12-15(18(23)24-16)10-13-6-2-1-3-7-13/h1-9,11-12H,10H2/b16-11-

Standard InChI Key:  LZRQABGJGDKGLN-WJDWOHSUSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   11.5604  -21.2406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8982  -21.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2385  -21.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4941  -20.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3090  -20.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8971  -22.5372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0200  -20.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7271  -20.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4344  -20.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1415  -20.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1376  -21.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4308  -21.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7237  -21.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5331  -21.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8245  -21.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1191  -21.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4084  -21.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4032  -20.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1087  -20.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8193  -20.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4352  -19.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1434  -18.8336    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.7280  -18.8321    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.4300  -18.4239    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
  9 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2228182

   (5Z)-3-benzyl-5-[[2-(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: 0.18

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