N-(2-(4-Ethylphenylamino)benzo[d]oxazol-5-yl)-2-chloro-5-nitrobenzamide

ID: ALA4071513

PubChem CID: 54765630

Max Phase: Preclinical

Molecular Formula: C22H17ClN4O4

Molecular Weight: 436.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc(Nc2nc3cc(NC(=O)c4cc([N+](=O)[O-])ccc4Cl)ccc3o2)cc1

Standard InChI:  InChI=1S/C22H17ClN4O4/c1-2-13-3-5-14(6-4-13)25-22-26-19-11-15(7-10-20(19)31-22)24-21(28)17-12-16(27(29)30)8-9-18(17)23/h3-12H,2H2,1H3,(H,24,28)(H,25,26)

Standard InChI Key:  IGNWUQGZXIQDTJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    4.4766  -13.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4755  -13.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1835  -14.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1817  -12.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8904  -13.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8951  -13.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6752  -14.1963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1525  -13.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6674  -12.8718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697  -13.5263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3741  -12.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1912  -12.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5956  -12.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1828  -11.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3614  -11.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9607  -12.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5862  -10.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1725   -9.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7688  -12.7244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686  -11.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0608  -11.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4762  -11.4984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0659  -10.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3589  -10.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6503  -10.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6532  -11.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3607  -11.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643  -12.7245    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3589   -9.4502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513   -9.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -9.0418    0.0000 O   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
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
 17 18  1  0
  1 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 21  1  0
 27 28  1  0
 29 30  2  0
 29 31  1  0
 24 29  1  0
M  CHG  2  29   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4071513

   2-chloro-N-[2-(4-ethylanilino)-1,3-benzoxazol-5-yl]-5-nitrobenzamide

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: 436.86

Molecular Weight (Monoisotopic): 436.0938

AlogP: 5.95

#Rotatable Bonds: 6

Polar Surface Area: 110.30

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.29

CX Basic pKa: ┄

CX LogP: 6.04

CX LogD: 6.04

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.29

Np Likeness Score: -1.98

References

1. Kim D, Won HY, Hwang ES, Kim YK, Choo HP..  (2017)  Synthesis of benzoxazole derivatives as interleukin-6 antagonists.,  25  (12): [PMID:28442260] [10.1016/j.bmc.2017.03.072]

Source

Source(1):

• Scientific Literature