1-Ethyl-N-(2-(hydroxymethyl)phenyl)-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxamide

ID: ALA550346

PubChem CID: 44190929

Max Phase: Preclinical

Molecular Formula: C20H17F3N2O3

Molecular Weight: 390.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1cc(C(=O)Nc2ccccc2CO)c(=O)c2ccc(C(F)(F)F)cc21

Standard InChI:  InChI=1S/C20H17F3N2O3/c1-2-25-10-15(19(28)24-16-6-4-3-5-12(16)11-26)18(27)14-8-7-13(9-17(14)25)20(21,22)23/h3-10,26H,2,11H2,1H3,(H,24,28)

Standard InChI Key:  CCUJMHXESAWQPY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -2.9205   -4.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9205   -5.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2060   -5.7097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2060   -4.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4915   -4.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4915   -5.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7771   -5.7097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0626   -5.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0626   -4.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7771   -4.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7771   -3.2347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6519   -4.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6519   -3.2347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3663   -4.4722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7771   -6.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0626   -6.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6349   -5.7097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3494   -6.1222    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2224   -6.4241    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0474   -4.9952    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3663   -2.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3663   -1.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0808   -1.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7953   -1.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7953   -2.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0808   -3.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6519   -1.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6519   -0.7597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  2 17  1  0
  5 10  1  0
 17 18  1  0
  6  7  1  0
 17 19  1  0
  7  8  1  0
 17 20  1  0
  8  9  2  0
 13 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 25  1  0
  9 12  1  0
 25 26  2  0
 26 21  1  0
  2  3  1  0
 22 27  1  0
 12 13  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA550346

   1-ethyl-N-[2-(hydroxymethyl)phenyl]-4-oxo-7-(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: 390.36

Molecular Weight (Monoisotopic): 390.1191

AlogP: 3.78

#Rotatable Bonds: 4

Polar Surface Area: 71.33

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.90

CX Basic pKa: ┄

CX LogP: 3.27

CX LogD: 3.27

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.71

Np Likeness Score: -1.29

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