N-(2-chloro-5-(trifluoromethyl)phenyl)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylamide

ID: ALA4789806

Cas Number: 380424-09-9

PubChem CID: 1527552

Max Phase: Preclinical

Molecular Formula: C18H12ClF3N2O3

Molecular Weight: 396.75

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C(\C#N)C(=O)Nc2cc(C(F)(F)F)ccc2Cl)ccc1O

Standard InChI:  InChI=1S/C18H12ClF3N2O3/c1-27-16-7-10(2-5-15(16)25)6-11(9-23)17(26)24-14-8-12(18(20,21)22)3-4-13(14)19/h2-8,25H,1H3,(H,24,26)/b11-6+

Standard InChI Key:  WLSVLYSVQYRXHB-IZZDOVSWSA-N

Molfile:  

 
     RDKit          2D

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   33.3335  -14.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1585  -14.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9210  -13.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9210  -14.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5065  -15.6237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0960  -13.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5710  -14.9104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5710  -13.4815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3960  -13.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6865  -12.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8623  -12.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4489  -13.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8658  -14.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6887  -14.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6265  -13.4803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4538  -14.9136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6288  -14.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8056  -14.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6298  -14.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0431  -13.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6262  -12.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8033  -12.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3889  -12.0553    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   37.0437  -14.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4187  -15.5644    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.7368  -15.7199    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   37.8947  -15.0522    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  4  5  3  0
  3  6  1  0
  2  7  2  0
  2  8  1  0
  8  9  1  0
  6 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  6  1  0
 12 15  1  0
 13 16  1  0
 16 17  1  0
  9 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  9  1  0
 22 23  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 19 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4789806

   N-[2-chloro-5-(trifluoromethyl)phenyl]-2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 396.75

Molecular Weight (Monoisotopic): 396.0489

AlogP: 4.62

#Rotatable Bonds: 4

Polar Surface Area: 82.35

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.88

CX Basic pKa: ┄

CX LogP: 4.40

CX LogD: 4.39

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: -1.23

References

1. Dalle Vedove A,Zonta F,Zanforlin E,Demitri N,Ribaudo G,Cazzanelli G,Ongaro A,Sarno S,Zagotto G,Battistutta R,Ruzzene M,Lolli G.  (2020)  A novel class of selective CK2 inhibitors targeting its open hinge conformation.,  195  [PMID:32283296] [10.1016/j.ejmech.2020.112267]

Source

Source(1):

• Scientific Literature