1-(4-(4-fluoro-2-methylphenylamino)-8-(2-(methylsulfinyl)ethoxy)quinolin-3-yl)butan-1-one

ID: ALA4090802

PubChem CID: 54443266

Max Phase: Preclinical

Molecular Formula: C23H25FN2O3S

Molecular Weight: 428.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC(=O)c1cnc2c(OCC[S+](C)[O-])cccc2c1Nc1ccc(F)cc1C

Standard InChI:  InChI=1S/C23H25FN2O3S/c1-4-6-20(27)18-14-25-23-17(7-5-8-21(23)29-11-12-30(3)28)22(18)26-19-10-9-16(24)13-15(19)2/h5,7-10,13-14H,4,6,11-12H2,1-3H3,(H,25,26)

Standard InChI Key:  WPQIQQOTBKRKGA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   16.9547  -11.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2396  -11.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5240  -11.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5145  -10.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2294   -9.8808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7933   -9.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7877   -9.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0665   -8.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3459   -9.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3482   -9.8991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0730  -10.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6175   -8.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6237   -7.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3442   -7.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0620   -7.8159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9025   -9.0695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1846   -8.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4696   -9.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7536   -8.6613    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.7507   -7.8329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0386   -9.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5027   -8.6367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4918   -7.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2120   -7.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2077   -6.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4806   -6.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7604   -6.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7771   -7.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4716   -5.3214    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.9303   -7.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
 11 10  2  0
  6 11  1  0
  9 12  2  0
 13 12  1  0
 14 13  2  0
 15 14  1  0
  8 15  2  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
  7 22  1  0
 22 23  1  0
 23 24  2  0
 25 24  1  0
 26 25  2  0
 27 26  1  0
 28 27  2  0
 23 28  1  0
 26 29  1  0
 24 30  1  0
M  CHG  2  19   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4090802

   1-[4-(4-Fluoro-2-methylanilino)-8-(2-methylsulfinylethoxy)quinolin-3-yl]butan-1-one

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: 428.53

Molecular Weight (Monoisotopic): 428.1570

AlogP: 5.17

#Rotatable Bonds: 9

Polar Surface Area: 74.28

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.52

CX LogP: 4.64

CX LogD: 4.64

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: -1.16

References

1. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

Source

Source(1):

• Scientific Literature