5,7-Difluoro-3-methyl-2-(4-(3-methylpiperidin-1-yl)phenyl)quinolin-4(1H)-one

ID: ALA4100871

PubChem CID: 129259188

Max Phase: Preclinical

Molecular Formula: C22H22F2N2O

Molecular Weight: 368.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(-c2ccc(N3CCCC(C)C3)cc2)[nH]c2cc(F)cc(F)c2c1=O

Standard InChI:  InChI=1S/C22H22F2N2O/c1-13-4-3-9-26(12-13)17-7-5-15(6-8-17)21-14(2)22(27)20-18(24)10-16(23)11-19(20)25-21/h5-8,10-11,13H,3-4,9,12H2,1-2H3,(H,25,27)

Standard InChI Key:  RNMJDESKYCFJRV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   11.0545   -9.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0703   -7.0749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3621   -6.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3668   -5.8341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6544   -5.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9372   -5.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9324   -6.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6448   -7.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0840   -5.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0888   -4.6006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7922   -5.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7876   -6.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4998   -7.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2171   -6.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9295   -7.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9248   -7.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6331   -8.3350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3501   -7.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0626   -8.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3407   -9.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6283   -9.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2076   -8.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4953   -7.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5087   -5.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6588   -4.5947    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2172   -7.0592    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.7785   -7.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  4  3  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  9  4  1  0
  9 10  2  0
 11  9  1  0
 12 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 15 14  1  0
 16 15  2  0
 16 17  1  0
 17 18  1  0
 19 18  1  0
  1 19  1  0
 20  1  1  0
 21 20  1  0
 17 21  1  0
 22 16  1  0
 23 22  2  0
 13 23  1  0
 11 24  1  0
  5 25  1  0
  7 26  1  0
 19 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100871

   ---

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: 368.43

Molecular Weight (Monoisotopic): 368.1700

AlogP: 5.02

#Rotatable Bonds: 2

Polar Surface Area: 36.10

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.32

CX LogP: 5.25

CX LogD: 5.25

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: -0.82

References

1. Hong WD, Gibbons PD, Leung SC, Amewu R, Stocks PA, Stachulski A, Horta P, Cristiano MLS, Shone AE, Moss D, Ardrey A, Sharma R, Warman AJ, Bedingfield PTP, Fisher NE, Aljayyoussi G, Mead S, Caws M, Berry NG, Ward SA, Biagini GA, O'Neill PM, Nixon GL..  (2017)  Rational Design, Synthesis, and Biological Evaluation of Heterocyclic Quinolones Targeting the Respiratory Chain of Mycobacterium tuberculosis.,  60  (9): [PMID:28304162] [10.1021/acs.jmedchem.6b01718]

Source

Source(1):

• Scientific Literature