3-(4-Fluorophenyl)-5-phenyl-6-carbethoxy-2-cyclohexen-1-one

ID: ALA2272754

PubChem CID: 5156916

Max Phase: Preclinical

Molecular Formula: C21H19FO3

Molecular Weight: 338.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1C(=O)C=C(c2ccc(F)cc2)CC1c1ccccc1

Standard InChI:  InChI=1S/C21H19FO3/c1-2-25-21(24)20-18(15-6-4-3-5-7-15)12-16(13-19(20)23)14-8-10-17(22)11-9-14/h3-11,13,18,20H,2,12H2,1H3

Standard InChI Key:  QWIIFQFGVSOWJH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   10.3119   -7.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0252   -7.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0252   -8.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3119   -8.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6029   -8.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6029   -7.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3119   -6.3270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8938   -7.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8938   -6.3270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1805   -7.5570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4715   -7.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7582   -7.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8938   -8.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8938   -9.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1805  -10.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4715   -9.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4715   -8.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1805   -8.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7384   -8.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4475   -8.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1607   -8.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1607   -9.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4475  -10.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7384   -9.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8739  -10.0209    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  1  7  2  0
  8  9  2  0
 11 12  1  0
 10 11  1  0
  8 10  1  0
  6  8  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
  5 13  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 22 25  1  0
  3 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2272754

   Ethyl 4-(4-fluorophenyl)-2-oxo-6-phenylcyclohex-3-ene-1-carboxylate

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: 338.38

Molecular Weight (Monoisotopic): 338.1318

AlogP: 4.15

#Rotatable Bonds: 4

Polar Surface Area: 43.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.65

CX Basic pKa: ┄

CX LogP: 4.80

CX LogD: 4.80

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.62

Np Likeness Score: -0.33

References

1. Shakil NA, Singh MK, Sathiyendiran M, Kumar J, Padaria JC..  (2013)  Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.,  59  [PMID:23229055] [10.1016/j.ejmech.2012.10.038]

Source

Source(1):

• Scientific Literature