3-(4-Fluoro-benzylidene)-5-(4-chloro-phenyl)-2(3H)-furanone

ID: ALA555227

PubChem CID: 712304

Max Phase: Preclinical

Molecular Formula: C17H10ClFO2

Molecular Weight: 300.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1OC(c2ccc(Cl)cc2)=C/C1=C\c1ccc(F)cc1

Standard InChI:  InChI=1S/C17H10ClFO2/c18-14-5-3-12(4-6-14)16-10-13(17(20)21-16)9-11-1-7-15(19)8-2-11/h1-10H/b13-9+

Standard InChI Key:  HRNOMVJWTAJPDO-UKTHLTGXSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    1.9720   -4.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2575   -4.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2575   -5.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720   -5.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6865   -5.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6865   -4.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720   -6.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3046   -7.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5595   -8.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3845   -8.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6395   -7.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8694   -8.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6899   -8.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255   -7.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8460   -7.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3309   -8.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9953   -9.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1748   -9.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0746   -8.6898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1514   -8.3448    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720   -3.4528    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11  7  2  0
  4  7  1  0
  5  6  2  0
 10 12  2  0
  6  1  1  0
 12 13  1  0
  7  8  1  0
 13 14  2  0
  1  2  2  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
 16 17  1  0
  4  5  1  0
 17 18  2  0
 18 13  1  0
  2  3  1  0
  1 21  1  0
  8  9  1  0
  9 19  2  0
  9 10  1  0
 16 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA555227

   (3E)-5-(4-chlorophenyl)-3-(4-fluorobenzylidene)furan-2(3H)-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: 300.72

Molecular Weight (Monoisotopic): 300.0353

AlogP: 4.46

#Rotatable Bonds: 2

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: 4.64

CX LogD: 4.64

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.60

Np Likeness Score: -0.61

References

1. Alam MM, Husain A, Hasan SM, Suruchi, Anwer T..  (2009)  Synthesis and pharmacological evaluation of 2(3H)-furanones and 2(3H)-pyrrolones, combining analgesic and anti-inflammatory properties with reduced gastrointestinal toxicity and lipid peroxidation.,  44  (6): [PMID:19059680] [10.1016/j.ejmech.2008.10.030]

2. Husain A, Khan SA, Iram F, Iqbal MA, Asif M..  (2019)  Insights into the chemistry and therapeutic potential of furanones: A versatile pharmacophore.,  171  [PMID:30909021] [10.1016/j.ejmech.2019.03.021]

Source

Source(1):

• Scientific Literature