N-(4-Aminobenzyl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide

ID: ALA552239

PubChem CID: 44190837

Max Phase: Preclinical

Molecular Formula: C19H18FN3O2

Molecular Weight: 339.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H18FN3O2/c1-2-23-11-16(18(24)15-9-13(20)5-8-17(15)23)19(25)22-10-12-3-6-14(21)7-4-12/h3-9,11H,2,10,21H2,1H3,(H,22,25)

Standard InChI Key:  IMEBUGGCICOOOG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -3.8659  -10.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8659  -11.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1514  -12.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1514  -10.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4370  -10.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4370  -11.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7225  -12.0149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0080  -11.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0080  -10.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7225  -10.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7225   -9.5399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2935  -10.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4209  -10.7774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2935   -9.5399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5804  -10.3649    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7225  -12.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0080  -13.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354  -10.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8499  -10.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5643  -10.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2788  -10.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2788  -11.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5643  -12.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8499  -11.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9933  -12.0149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  9 12  1  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 12 14  2  0
  1  2  2  0
  1 15  1  0
  5  4  2  0
  7 16  1  0
  4  1  1  0
 16 17  1  0
  5 10  1  0
 13 18  1  0
  6  7  1  0
 18 19  1  0
  7  8  1  0
 19 20  2  0
  8  9  2  0
 20 21  1  0
  9 10  1  0
 21 22  2  0
  5  6  1  0
 22 23  1  0
 10 11  2  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA552239

   N-[(4-aminophenyl)methyl]-1-ethyl-6-fluoro-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: 339.37

Molecular Weight (Monoisotopic): 339.1383

AlogP: 2.67

#Rotatable Bonds: 4

Polar Surface Area: 77.12

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.17

CX LogP: 2.18

CX LogD: 2.18

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.72

Np Likeness Score: -1.58

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