1-[8-(3-Dimethylamino-propoxy)-4-(4-fluoro-2-methyl-phenylamino)-quinolin-3-yl]-butan-1-one

ID: ALA93579

PubChem CID: 10477403

Max Phase: Preclinical

Molecular Formula: C25H30FN3O2

Molecular Weight: 423.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC(=O)c1cnc2c(OCCCN(C)C)cccc2c1Nc1ccc(F)cc1C

Standard InChI:  InChI=1S/C25H30FN3O2/c1-5-8-22(30)20-16-27-25-19(9-6-10-23(25)31-14-7-13-29(3)4)24(20)28-21-12-11-18(26)15-17(21)2/h6,9-12,15-16H,5,7-8,13-14H2,1-4H3,(H,27,28)

Standard InChI Key:  YZMUDYASWPWNPJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    2.7625   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -4.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500   -4.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625   -3.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542   -5.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500   -5.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -5.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125   -2.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -4.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -5.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -3.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875   -2.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167   -1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833   -9.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9667   -0.6917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -6.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -8.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -4.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042   -4.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833   -8.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -5.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -7.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375   -9.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958   -9.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -4.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3375   -4.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  1  1  0
  5  6  1  0
  6  3  1  0
  7  2  1  0
  8  4  1  0
  9  2  1  0
 10  8  1  0
 11  6  2  0
 12 10  2  0
 13  9  2  0
 14  8  2  0
 15 18  2  0
 16 25  1  0
 17  3  2  0
 18 14  1  0
 19 15  1  0
 20 11  1  0
 21 27  1  0
 22 17  1  0
 23 10  1  0
 24  9  1  0
 25 21  1  0
 26 22  2  0
 27 20  1  0
 28 16  1  0
 29 16  1  0
 30 24  1  0
 31 30  1  0
  5  7  2  0
 11 26  1  0
 15 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA93579

   3-Butyryl-4-(4-fluoro-2-methylphenyl-amino)-8-(3-dimethylaminopropoxy)quinoline

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: 423.53

Molecular Weight (Monoisotopic): 423.2322

AlogP: 5.74

#Rotatable Bonds: 10

Polar Surface Area: 54.46

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.26

CX LogP: 6.15

CX LogD: 4.30

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.33

Np Likeness Score: -1.38

References

1. Leach CA, Brown TH, Ife RJ, Keeling DJ, Parsons ME, Theobald CJ, Wiggall KJ..  (1995)  Reversible inhibitors of the gastric (H+/K+)-ATPase. 4. Identification of an inhibitor with an intermediate duration of action.,  38  (14): [PMID:7629813] [10.1021/jm00014a026]

Source

Source(1):

• Scientific Literature