4-(4-chloro-2-fluorophenylamino)-6,7-dimethoxy-N-methylquinoline-3-carboxamide

ID: ALA4783492

PubChem CID: 118704900

Max Phase: Preclinical

Molecular Formula: C19H17ClFN3O3

Molecular Weight: 389.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cnc2cc(OC)c(OC)cc2c1Nc1ccc(Cl)cc1F

Standard InChI:  InChI=1S/C19H17ClFN3O3/c1-22-19(25)12-9-23-15-8-17(27-3)16(26-2)7-11(15)18(12)24-14-5-4-10(20)6-13(14)21/h4-9H,1-3H3,(H,22,25)(H,23,24)

Standard InChI Key:  MXBCVSLLTIRSIL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    5.0586   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0574   -3.7622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7655   -4.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7637   -2.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4723   -2.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4731   -3.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1816   -4.1652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8899   -3.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8851   -2.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1760   -2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5917   -2.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3018   -2.9231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5867   -1.7016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1717   -1.7117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4618   -1.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4629   -0.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7539   -0.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474   -0.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0544   -1.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7640   -1.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3494   -4.1702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3487   -4.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0071   -2.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508   -2.5342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6431   -2.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1699   -0.0813    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3370   -0.0949    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  1  0
 11 13  2  0
  9 11  1  0
 10 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  2 21  1  0
 21 22  1  0
 12 23  1  0
  1 24  1  0
 24 25  1  0
 16 26  1  0
 18 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4783492

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 389.81

Molecular Weight (Monoisotopic): 389.0942

AlogP: 4.15

#Rotatable Bonds: 5

Polar Surface Area: 72.48

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.53

CX LogP: 4.38

CX LogD: 4.32

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: -1.42

References

1. Kettle JG,Alwan H,Bista M,Breed J,Davies NL,Eckersley K,Fillery S,Foote KM,Goodwin L,Jones DR,Käck H,Lau A,Nissink JW,Read J,Scott JS,Taylor B,Walker G,Wissler L,Wylot M.  (2016)  Potent and Selective Inhibitors of MTH1 Probe Its Role in Cancer Cell Survival.,  59  (6): [PMID:26878898] [10.1021/acs.jmedchem.5b01760]

Source

Source(1):

• Scientific Literature