(E)-N-(7-chloroquinolin-4-yl)-3-(3-fluorophenyl)acrylamide

ID: ALA2042194

PubChem CID: 66573731

Max Phase: Preclinical

Molecular Formula: C18H12ClFN2O

Molecular Weight: 326.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cccc(F)c1)Nc1ccnc2cc(Cl)ccc12

Standard InChI:  InChI=1S/C18H12ClFN2O/c19-13-5-6-15-16(8-9-21-17(15)11-13)22-18(23)7-4-12-2-1-3-14(20)10-12/h1-11H,(H,21,22,23)/b7-4+

Standard InChI Key:  XBQRYXQEDNEHKO-QPJJXVBHSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -0.0110    1.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7057    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4180    1.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1346    0.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1390   -0.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8557   -0.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5679   -0.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8469    1.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0153    1.8657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7232    0.6244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7101   -1.8505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0022   -1.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0022   -0.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7188   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4311   -0.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1478   -0.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600   -0.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557   -1.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1390   -1.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4267   -1.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5679   -1.8657    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5635    0.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780    1.0597    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  2  0
  6  7  1  0
  7 22  2  0
 22  8  1  0
  4  8  2  0
  1  9  2  0
  1 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 11 20  1  0
 15 20  1  0
 18 21  1  0
 10 14  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2042194

   (E)-N-(7-chloro-4-quinolyl)-3-(3-fluorophenyl)prop-2-enamide

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: 326.76

Molecular Weight (Monoisotopic): 326.0622

AlogP: 4.68

#Rotatable Bonds: 3

Polar Surface Area: 41.99

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.45

CX Basic pKa: 4.21

CX LogP: 4.47

CX LogD: 4.47

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.71

Np Likeness Score: -1.46

References

1. Pérez BC, Teixeira C, Figueiras M, Gut J, Rosenthal PJ, Gomes JR, Gomes P..  (2012)  Novel cinnamic acid/4-aminoquinoline conjugates bearing non-proteinogenic amino acids: towards the development of potential dual action antimalarials.,  54  [PMID:22683112] [10.1016/j.ejmech.2012.05.022]

Source

Source(1):

• Scientific Literature