5-{2-Fluoro-4-[2-(2-fluoro-benzyl)-3-oxo-cyclohex-1-enylamino]-phenyl}-4,4-dimethyl-2,4-dihydro-pyrazol-3-one

ID: ALA131672

PubChem CID: 23647054

Max Phase: Preclinical

Molecular Formula: C24H23F2N3O2

Molecular Weight: 423.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C(=O)NN=C1c1ccc(NC2=C(Cc3ccccc3F)C(=O)CCC2)cc1F

Standard InChI:  InChI=1S/C24H23F2N3O2/c1-24(2)22(28-29-23(24)31)16-11-10-15(13-19(16)26)27-20-8-5-9-21(30)17(20)12-14-6-3-4-7-18(14)25/h3-4,6-7,10-11,13,27H,5,8-9,12H2,1-2H3,(H,29,31)

Standard InChI Key:  VDLINFRONRFGGR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    4.0542   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667    1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -4.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667    0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542    2.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542    0.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792    2.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750   -0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542    2.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -4.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    3.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875    2.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -2.0250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -3.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292    2.9375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792    0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2000    1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2000    0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750    3.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792    4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625    4.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  8  2  0
  5  1  1  0
  6  3  1  0
  7  2  1  0
  8 11  1  0
  9  4  1  0
 10  5  2  0
 11 16  1  0
 12  4  1  0
 13 10  1  0
 14  5  1  0
 15  9  1  0
 16 21  1  0
 17  7  2  0
 18 15  1  0
 19 12  2  0
 20 10  1  0
 21 14  2  0
 22  2  1  0
 23  2  1  0
 24 18  1  0
 25  8  1  0
 26 27  1  0
 27 25  1  0
 28 15  2  0
 29 18  2  0
 30 28  1  0
 31 30  2  0
  6  7  1  0
 16 13  2  0
 26 12  1  0
 31 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA131672

   3-[2-fluoro-4-({2-[(2-fluorophenyl)methyl]-3-oxocyclohex-1-en-1-yl}amino)phenyl]-4,4-dimethyl-4,5-dihydro-1H-pyrazol-5-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: 423.46

Molecular Weight (Monoisotopic): 423.1758

AlogP: 4.49

#Rotatable Bonds: 5

Polar Surface Area: 70.56

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.64

CX Basic pKa: 1.68

CX LogP: 4.55

CX LogD: 4.55

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.74

Np Likeness Score: -0.63

References

1. Edmondson SD, Mastracchio A, He J, Chung CC, Forrest MJ, Hofsess S, MacIntyre E, Metzger J, O'Connor N, Patel K, Tong X, Tota MR, Van der Ploeg LH, Varnerin JP, Fisher MH, Wyvratt MJ, Weber AE, Parmee ER..  (2003)  Benzyl vinylogous amide substituted aryldihydropyridazinones and aryldimethylpyrazolones as potent and selective PDE3B inhibitors.,  13  (22): [PMID:14592490] [10.1016/j.bmcl.2003.08.056]

Source

Source(1):

• Scientific Literature