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

ID: ALA2272753

PubChem CID: 5173480

Max Phase: Preclinical

Molecular Formula: C21H18FNO5

Molecular Weight: 383.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1C(=O)C=C(c2ccc(F)cc2)CC1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C21H18FNO5/c1-2-28-21(25)20-18(14-4-3-5-17(10-14)23(26)27)11-15(12-19(20)24)13-6-8-16(22)9-7-13/h3-10,12,18,20H,2,11H2,1H3

Standard InChI Key:  FKPIHMWYZYRBSX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    3.4603  -10.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7554  -10.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0421  -10.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0421   -9.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7554   -8.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603   -9.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1735  -10.4171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1735   -8.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8826   -9.1872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1735   -7.9532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8826   -7.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8826   -6.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7554   -7.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0421   -7.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0421   -6.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7554   -6.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603   -6.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603   -7.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289   -6.3105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289   -5.4892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6157   -6.7233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289  -10.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289  -11.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6157  -11.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0965  -11.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0965  -10.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6157  -10.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113  -11.6512    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
 19 20  2  0
 19 21  1  0
 15 19  1  0
  5 13  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 22 27  2  0
 25 28  1  0
  3 22  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2272753

   Ethyl 4-(4-fluorophenyl)-6-(3-nitrophenyl)-2-oxocyclohex-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: 383.38

Molecular Weight (Monoisotopic): 383.1169

AlogP: 4.05

#Rotatable Bonds: 5

Polar Surface Area: 86.51

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.77

CX Basic pKa: ┄

CX LogP: 4.74

CX LogD: 4.74

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.34

Np Likeness Score: -0.76

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