3-chloro-N-(4-(5-(4-methoxyphenyl)-4,5-dihydroisoxazol-3-yl)phenyl)-1H-indole-2-carboxamide

ID: ALA4170619

PubChem CID: 145951110

Max Phase: Preclinical

Molecular Formula: C25H20ClN3O3

Molecular Weight: 445.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2CC(c3ccc(NC(=O)c4[nH]c5ccccc5c4Cl)cc3)=NO2)cc1

Standard InChI:  InChI=1S/C25H20ClN3O3/c1-31-18-12-8-16(9-13-18)22-14-21(29-32-22)15-6-10-17(11-7-15)27-25(30)24-23(26)19-4-2-3-5-20(19)28-24/h2-13,22,28H,14H2,1H3,(H,27,30)

Standard InChI Key:  KHDXAHCWSNRZSF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   27.3786   -9.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3775  -10.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0896  -10.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0879   -9.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8006   -9.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8054  -10.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5896  -10.8326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0710  -10.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5818   -9.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8298   -8.7459    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.8923  -10.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3051  -10.8679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2968   -9.4443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1181   -9.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5329  -10.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3534  -10.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7587   -9.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3415   -8.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5223   -8.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5814   -9.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0706  -10.0835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8501   -9.8253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.8442   -9.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0611   -8.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5049   -8.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2543   -8.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9156   -8.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8246   -7.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0666   -7.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4084   -7.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4857   -7.0533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2392   -7.3834    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  1  0
  8  9  2  0
  9  5  1  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
 17 20  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
 23 25  1  0
 28 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4170619

   ---

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: 445.91

Molecular Weight (Monoisotopic): 445.1193

AlogP: 5.95

#Rotatable Bonds: 5

Polar Surface Area: 75.71

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.85

CX Basic pKa: 2.55

CX LogP: 5.20

CX LogD: 5.20

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.40

Np Likeness Score: -1.06

References

1. Keri RS, Chand K, Budagumpi S, Balappa Somappa S, Patil SA, Nagaraja BM..  (2017)  An overview of benzo[b]thiophene-based medicinal chemistry.,  138  [PMID:28759875] [10.1016/j.ejmech.2017.07.038]

Source

Source(1):

• Scientific Literature