7-(4-Carbamoylpiperidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

ID: ALA550018

PubChem CID: 44191021

Max Phase: Preclinical

Molecular Formula: C19H20FN3O4

Molecular Weight: 373.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)C1CCN(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3C2CC2)CC1

Standard InChI:  InChI=1S/C19H20FN3O4/c20-14-7-12-15(8-16(14)22-5-3-10(4-6-22)18(21)25)23(11-1-2-11)9-13(17(12)24)19(26)27/h7-11H,1-6H2,(H2,21,25)(H,26,27)

Standard InChI Key:  AXIOIJYCBYMNOP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    4.9984   -3.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9984   -3.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7129   -4.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7129   -2.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4274   -3.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4274   -3.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1419   -4.2681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8563   -3.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8563   -3.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1419   -2.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2840   -4.2681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5695   -3.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8550   -4.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8550   -5.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5695   -5.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2840   -5.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1419   -1.7931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5708   -2.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5708   -1.7931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2853   -3.0306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2840   -2.6181    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406   -5.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406   -6.3306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4261   -5.0931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1419   -5.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7294   -5.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5544   -5.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  5  4  2  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
  6  7  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  1  0
  5  6  1  0
 22 24  2  0
  7 25  1  0
 26 25  1  0
 27 26  1  0
 25 27  1  0
  2  3  1  0
  3  6  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA550018

   7-(4-Carbamoylpiperidin-1-yl)-1-cyclopropyl-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: 373.38

Molecular Weight (Monoisotopic): 373.1438

AlogP: 1.88

#Rotatable Bonds: 4

Polar Surface Area: 105.63

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.87

CX Basic pKa: 0.65

CX LogP: 1.36

CX LogD: -0.18

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.85

Np Likeness Score: -0.99

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]

2. Hiltensperger G, Jones NG, Niedermeier S, Stich A, Kaiser M, Jung J, Puhl S, Damme A, Braunschweig H, Meinel L, Engstler M, Holzgrabe U..  (2012)  Synthesis and structure-activity relationships of new quinolone-type molecules against Trypanosoma brucei.,  55  (6): [PMID:22376072] [10.1021/jm101439s]

Source

Source(1):

• Scientific Literature