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

ID: ALA2289591

PubChem CID: 15008455

Max Phase: Preclinical

Molecular Formula: C20H19Cl2N3O2

Molecular Weight: 404.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1nn(C)c(C(=O)NCc2ccc(Oc3ccc(Cl)cc3)cc2)c1Cl

Standard InChI:  InChI=1S/C20H19Cl2N3O2/c1-3-17-18(22)19(25(2)24-17)20(26)23-12-13-4-8-15(9-5-13)27-16-10-6-14(21)7-11-16/h4-11H,3,12H2,1-2H3,(H,23,26)

Standard InChI Key:  ZCJYNFNJUQPDSI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   10.9911  -10.5084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6274  -11.0185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3092  -10.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0943   -9.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2798   -9.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5885  -11.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8314   -9.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0155   -9.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6055   -9.1468    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.0221  -10.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0330  -11.7876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7243  -10.5524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4374  -10.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1396  -10.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8487  -10.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5504  -10.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5399   -9.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8218   -9.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1231   -9.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2416   -9.2810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9552   -9.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9627  -10.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6755  -10.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3781  -10.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3634   -9.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6501   -9.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0923  -10.8729    0.0000 Cl  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
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289591

   4-chloro-N-[[4-(4-chlorophenoxy)phenyl]methyl]-5-ethyl-2-methylpyrazole-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: 404.30

Molecular Weight (Monoisotopic): 403.0854

AlogP: 5.01

#Rotatable Bonds: 6

Polar Surface Area: 56.15

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.15

CX Basic pKa: 1.32

CX LogP: 4.66

CX LogD: 4.66

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: -1.31

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]

2. Preston S,Garcia-Bustos J,Hall LG,Martin SD,Le TG,Kundu A,Ghoshal A,Nguyen NH,Jiao Y,Ruan B,Xue L,Huang F,Chang BCH,McGee SL,Wells TNC,Palmer MJ,Jabbar A,Gasser RB,Baell JB.  (2021)  1-Methyl-1H-pyrazole-5-carboxamide Derivatives Exhibit Unexpected Acute Mammalian Toxicity.,  64  (1.0): [PMID:33352050] [10.1021/acs.jmedchem.0c01793]

Source

Source(1):

• Scientific Literature