7-[4-(Ethoxycarbonyl)piperidin-1-yl]-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

ID: ALA557886

PubChem CID: 44191022

Max Phase: Preclinical

Molecular Formula: C20H23FN2O5

Molecular Weight: 390.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1CCN(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3CC)CC1

Standard InChI:  InChI=1S/C20H23FN2O5/c1-3-22-11-14(19(25)26)18(24)13-9-15(21)17(10-16(13)22)23-7-5-12(6-8-23)20(27)28-4-2/h9-12H,3-8H2,1-2H3,(H,25,26)

Standard InChI Key:  DNRKSKJYLJJTLU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -0.5841   -5.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5841   -6.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1304   -6.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1304   -4.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8449   -5.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8449   -6.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5593   -6.5550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738   -6.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738   -5.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5593   -4.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -6.5550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0130   -6.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7275   -6.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7275   -7.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0130   -7.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -7.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5593   -4.0800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -4.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -4.0800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7027   -5.3175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -4.9050    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4420   -7.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1564   -7.3800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4420   -8.6175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1564   -9.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1564   -9.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5593   -7.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738   -7.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  2 11  1  0
  4  1  1  0
 10 17  2  0
  5 10  1  0
  9 18  1  0
  7  6  1  0
 18 19  1  0
  7  8  1  0
 18 20  2  0
  8  9  2  0
  1 21  1  0
  9 10  1  0
 14 22  1  0
 11 12  1  0
 22 23  2  0
  5  6  1  0
  2  3  1  0
  3  6  2  0
 22 24  1  0
  1  2  2  0
 24 25  1  0
  5  4  2  0
 25 26  1  0
  7 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA557886

   7-(4-Ethoxycarbonylpiperidin-1-yl)-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid

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: 390.41

Molecular Weight (Monoisotopic): 390.1591

AlogP: 2.64

#Rotatable Bonds: 5

Polar Surface Area: 88.84

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.88

CX Basic pKa: 0.68

CX LogP: 2.56

CX LogD: 1.03

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.79

Np Likeness Score: -1.01

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