N-(2-(4-methoxyphenylamino)-4-methylquinolin-6-yl)-1H-indole-2-carboxamide

ID: ALA3325857

PubChem CID: 20910538

Max Phase: Preclinical

Molecular Formula: C26H22N4O2

Molecular Weight: 422.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Nc2cc(C)c3cc(NC(=O)c4cc5ccccc5[nH]4)ccc3n2)cc1

Standard InChI:  InChI=1S/C26H22N4O2/c1-16-13-25(27-18-7-10-20(32-2)11-8-18)30-23-12-9-19(15-21(16)23)28-26(31)24-14-17-5-3-4-6-22(17)29-24/h3-15,29H,1-2H3,(H,27,30)(H,28,31)

Standard InChI Key:  XIHGBLWCWSAVQN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    5.3783   -6.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3772   -7.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0921   -8.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0903   -6.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8058   -6.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8065   -7.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5220   -8.0476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2370   -7.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2323   -6.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5163   -6.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5119   -5.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6637   -6.4009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9492   -6.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346   -6.4012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9494   -7.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2813   -8.1247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6163   -8.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3617   -8.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5384   -8.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1277   -9.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5391  -10.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3655  -10.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7725   -9.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9532   -8.0426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6661   -7.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3795   -8.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0919   -7.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0892   -6.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3679   -6.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6584   -6.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8016   -6.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5182   -6.7934    0.0000 C   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
 10 11  1  0
  1 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 19  1  0
 18 17  1  0
 17 15  2  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  8 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3325857

   N-{2-[(4-methoxyphenyl)amino]-4-methylquinolin-6-yl}-1H-indole-2-carboxamide

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: 422.49

Molecular Weight (Monoisotopic): 422.1743

AlogP: 6.03

#Rotatable Bonds: 5

Polar Surface Area: 79.04

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.90

CX Basic pKa: 6.19

CX LogP: 5.63

CX LogD: 5.61

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: -1.32

References

1. Kher SS, Penzo M, Fulle S, Finn PW, Blackman MJ, Jirgensons A..  (2014)  Substrate derived peptidic α-ketoamides as inhibitors of the malarial protease PfSUB1.,  24  (18): [PMID:25129616] [10.1016/j.bmcl.2014.07.086]

2. Lidumniece E, Withers-Martinez C, Hackett F, Blackman MJ, Jirgensons A..  (2022)  Subtilisin-like Serine Protease 1 (SUB1) as an Emerging Antimalarial Drug Target: Current Achievements in Inhibitor Discovery.,  65  (19.0): [PMID:36137276] [10.1021/acs.jmedchem.2c01093]

Source

Source(1):

• Scientific Literature