1-Ethyl-N-(4-methoxy-benzyl)-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxamide

ID: ALA558352

PubChem CID: 30133538

Max Phase: Preclinical

Molecular Formula: C21H19F3N2O3

Molecular Weight: 404.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1cc(C(=O)NCc2ccc(OC)cc2)c(=O)c2cc(C(F)(F)F)ccc21

Standard InChI:  InChI=1S/C21H19F3N2O3/c1-3-26-12-17(20(28)25-11-13-4-7-15(29-2)8-5-13)19(27)16-10-14(21(22,23)24)6-9-18(16)26/h4-10,12H,3,11H2,1-2H3,(H,25,28)

Standard InChI Key:  STBOJOLARVYICG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -3.5737   -1.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5737   -2.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592   -2.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1447   -1.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1447   -2.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302   -2.6358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158   -2.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158   -1.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302   -0.1608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132   -1.3983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013   -0.1608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302   -3.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158   -3.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4276   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2881   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0026   -0.5733    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7006   -1.7003    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8756   -0.2713    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421   -1.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5711   -1.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5711   -2.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566   -2.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421   -2.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2855   -2.6358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000   -2.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  2  0
  1  2  2  0
  7 15  1  0
  5  4  2  0
 15 16  1  0
  4  1  1  0
 13 17  1  0
  5 10  1  0
  1 18  1  0
  6  7  1  0
 18 19  1  0
  7  8  1  0
 18 20  1  0
  8  9  2  0
 18 21  1  0
  9 10  1  0
 17 22  1  0
  5  6  1  0
 22 23  2  0
 10 11  2  0
 23 24  1  0
 24 25  2  0
  9 12  1  0
 25 26  1  0
  2  3  1  0
 26 27  2  0
 27 22  1  0
 12 13  1  0
 25 28  1  0
  3  6  2  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA558352

   1-ethyl-N-[(4-methoxyphenyl)methyl]-4-oxo-6-(trifluoromethyl)quinoline-3-carboxamide

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: 404.39

Molecular Weight (Monoisotopic): 404.1348

AlogP: 3.98

#Rotatable Bonds: 5

Polar Surface Area: 60.33

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.30

CX LogP: 3.59

CX LogD: 3.59

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: -1.45

References

1. Niedermeier S, Singethan K, Rohrer SG, Matz M, Kossner M, Diederich S, Maisner A, Schmitz J, Hiltensperger G, Baumann K, Holzgrabe U, Schneider-Schaulies J..  (2009)  A small-molecule inhibitor of Nipah virus envelope protein-mediated membrane fusion.,  52  (14): [PMID:19499921] [10.1021/jm900411s]

Source

Source(1):

• Scientific Literature