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

ID: ALA2228178

PubChem CID: 24861987

Max Phase: Preclinical

Molecular Formula: C18H9F5O2

Molecular Weight: 352.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1O/C(=C\c2c(F)c(F)c(F)c(F)c2F)C=C1Cc1ccccc1

Standard InChI:  InChI=1S/C18H9F5O2/c19-13-12(14(20)16(22)17(23)15(13)21)8-11-7-10(18(24)25-11)6-9-4-2-1-3-5-9/h1-5,7-8H,6H2/b11-8-

Standard InChI Key:  NNXNZONKZYMLJC-FLIBITNWSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   20.9416  -16.6717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2794  -17.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6197  -16.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8753  -15.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6902  -15.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2783  -17.9683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4012  -15.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1083  -15.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8156  -15.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5227  -15.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5188  -16.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8120  -17.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1049  -16.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9143  -17.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2057  -16.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5003  -17.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7896  -16.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7844  -15.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4899  -15.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2005  -15.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2252  -17.1321    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.8164  -14.6726    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.2323  -15.4972    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.8094  -17.9452    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.3954  -17.1208    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
 11 21  1  0
  9 22  1  0
 10 23  1  0
 12 24  1  0
 13 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2228178

   (5Z)-3-benzyl-5-[(2,3,4,5,6-pentafluorophenyl)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: 352.26

Molecular Weight (Monoisotopic): 352.0523

AlogP: 4.45

#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: 5.05

CX LogD: 5.05

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.35

Np Likeness Score: 0.41

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