5-fluoro-4-oxo-1-(4-(pyridin-3-yl)benzyl)-1,4-dihydroquinoline-3-carboxylic acid

ID: ALA608399

PubChem CID: 24963516

Max Phase: Preclinical

Molecular Formula: C22H15FN2O3

Molecular Weight: 374.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cn(Cc2ccc(-c3cccnc3)cc2)c2cccc(F)c2c1=O

Standard InChI:  InChI=1S/C22H15FN2O3/c23-18-4-1-5-19-20(18)21(26)17(22(27)28)13-25(19)12-14-6-8-15(9-7-14)16-3-2-10-24-11-16/h1-11,13H,12H2,(H,27,28)

Standard InChI Key:  RWAHKTYMXPBNIM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   10.6252  -12.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6241  -13.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3396  -14.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3378  -12.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0539  -12.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0546  -13.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7705  -14.0849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4863  -13.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4815  -12.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7649  -12.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7605  -11.6056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1955  -12.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9132  -12.8298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1905  -11.5954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7723  -14.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4903  -15.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4969  -16.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2163  -16.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9273  -16.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9143  -15.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1944  -14.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6467  -16.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6567  -17.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3765  -17.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0870  -17.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3524  -16.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0714  -16.4935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3353  -11.6106    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  2  0
  9 12  1  0
  6  7  1  0
  7 15  1  0
  1  2  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
  5  4  2  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
  4  1  1  0
 19 20  1  0
  9 10  1  0
 20 21  2  0
 21 16  1  0
 10  5  1  0
 22 23  2  0
 10 11  2  0
 23 24  1  0
  2  3  1  0
 24 25  2  0
 25 27  1  0
 26 22  1  0
 19 22  1  0
 26 27  2  0
  5  6  1  0
  3  6  2  0
 12 13  1  0
  4 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA608399

   5-Fluoro-4-oxo-1-[(4-pyridin-3-ylphenyl)methyl]quinoline-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: 374.37

Molecular Weight (Monoisotopic): 374.1067

AlogP: 3.95

#Rotatable Bonds: 4

Polar Surface Area: 72.19

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.09

CX Basic pKa: 4.71

CX LogP: 3.47

CX LogD: 2.32

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.59

Np Likeness Score: -1.15

References

1. Yang FV, Shipe WD, Bunda JL, Nolt MB, Wisnoski DD, Zhao Z, Barrow JC, Ray WJ, Ma L, Wittmann M, Seager MA, Koeplinger KA, Hartman GD, Lindsley CW..  (2010)  Parallel synthesis of N-biaryl quinolone carboxylic acids as selective M(1) positive allosteric modulators.,  20  (2): [PMID:20004574] [10.1016/j.bmcl.2009.11.100]

Source

Source(1):

• Scientific Literature