7-Chloro-1-ethyl-6-fluoro-N-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

ID: ALA563338

PubChem CID: 44190927

Max Phase: Preclinical

Molecular Formula: C20H18ClFN2O3

Molecular Weight: 388.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1cc(C(=O)NCc2ccc(OC)cc2)c(=O)c2cc(F)c(Cl)cc21

Standard InChI:  InChI=1S/C20H18ClFN2O3/c1-3-24-11-15(19(25)14-8-17(22)16(21)9-18(14)24)20(26)23-10-12-4-6-13(27-2)7-5-12/h4-9,11H,3,10H2,1-2H3,(H,23,26)

Standard InChI Key:  ZAKYLIVEGOFMPI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    2.8225   -2.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8225   -3.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5370   -3.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5370   -2.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2515   -2.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2515   -3.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9659   -3.7895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6804   -3.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6804   -2.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9659   -2.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9659   -1.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3949   -2.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3949   -1.3145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1094   -2.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9659   -4.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6804   -5.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1094   -0.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1094   -0.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3949    0.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3949    1.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1094    1.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8238    1.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8238    0.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1094    2.3980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8238    2.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1081   -2.1395    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.1081   -3.7895    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  3  6  2  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
 17 18  1  0
  6  7  1  0
 18 19  2  0
  7  8  1  0
 19 20  1  0
  8  9  2  0
 20 21  2  0
  9 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 18  1  0
 10 11  2  0
 21 24  1  0
 24 25  1  0
  9 12  1  0
  1 26  1  0
  2  3  1  0
  2 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA563338

   7-chloro-1-ethyl-6-fluoro-N-[(4-methoxyphenyl)methyl]-4-oxoquinoline-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: 388.83

Molecular Weight (Monoisotopic): 388.0990

AlogP: 3.75

#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: ┄

CX LogP: 3.46

CX LogD: 3.46

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.72

Np Likeness Score: -1.54

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