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

ID: ALA2042199

PubChem CID: 66573798

Max Phase: Preclinical

Molecular Formula: C18H12ClN3O3

Molecular Weight: 353.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cccc([N+](=O)[O-])c1)Nc1ccnc2cc(Cl)ccc12

Standard InChI:  InChI=1S/C18H12ClN3O3/c19-13-5-6-15-16(8-9-20-17(15)11-13)21-18(23)7-4-12-2-1-3-14(10-12)22(24)25/h1-11H,(H,20,21,23)/b7-4+

Standard InChI Key:  YISUEBWYGOLAKI-QPJJXVBHSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    0.0000    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.4437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.8562    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
 12 13  2  0
 12 14  1  0
  8 12  1  0
  3  6  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 15 24  1  0
 19 24  1  0
 22 25  1  0
  5 18  1  0
M  CHG  2  12   1  14  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2042199

   (E)-N-(7-chloro-4-quinolyl)-3-(3-nitrophenyl)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: 353.77

Molecular Weight (Monoisotopic): 353.0567

AlogP: 4.45

#Rotatable Bonds: 4

Polar Surface Area: 85.13

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.45

CX Basic pKa: 4.21

CX LogP: 4.27

CX LogD: 4.27

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.43

Np Likeness Score: -1.48

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