4-chloro-3-ethyl-1-methyl-N-(4-(4-nitrophenoxy)benzyl)-1H-pyrazole-5-carboxamide

ID: ALA2289582

PubChem CID: 15008464

Max Phase: Preclinical

Molecular Formula: C20H19ClN4O4

Molecular Weight: 414.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1nn(C)c(C(=O)NCc2ccc(Oc3ccc([N+](=O)[O-])cc3)cc2)c1Cl

Standard InChI:  InChI=1S/C20H19ClN4O4/c1-3-17-18(21)19(24(2)23-17)20(26)22-12-13-4-8-15(9-5-13)29-16-10-6-14(7-11-16)25(27)28/h4-11H,3,12H2,1-2H3,(H,22,26)

Standard InChI Key:  PWBUKCVFLIWIDS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   20.9666  -18.1190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6029  -18.6291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2847  -18.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0698  -17.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2553  -17.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5640  -19.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8069  -16.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9910  -16.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5810  -16.7574    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.9976  -18.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0085  -19.3982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6998  -18.1631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4129  -18.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1151  -18.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8242  -18.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5259  -18.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5154  -17.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7974  -16.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0986  -17.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2171  -16.8916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9307  -17.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9382  -18.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6510  -18.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3536  -18.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3389  -17.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6256  -16.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0697  -18.4846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7707  -18.0647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0827  -19.3017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  2  6  1  0
  5  7  1  0
  7  8  1  0
  4  9  1  0
  3 10  1  0
 10 11  2  0
 10 12  1  0
 12 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
 17 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 27 28  2  0
 27 29  1  0
 24 27  1  0
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2289582

   4-chloro-5-ethyl-2-methyl-N-[[4-(4-nitrophenoxy)phenyl]methyl]pyrazole-3-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: 414.85

Molecular Weight (Monoisotopic): 414.1095

AlogP: 4.27

#Rotatable Bonds: 7

Polar Surface Area: 99.29

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.15

CX Basic pKa: 1.32

CX LogP: 4.00

CX LogD: 4.00

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: -1.46

References

1. OKADA I, OKUI S, WADA M, TAKAHASHI Y.  (1996)  Synthesis and Insecticidal Activity of N-(4-Aryloxybenzyl)-pyrazolecarboxamide Derivatives,  21  (3): [10.1584/jpestics.21.305]

Source

Source(1):

• Scientific Literature