2,6-dimethyl-N-(4-(4-nitrophenoxy)benzyl)-2,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxamide

ID: ALA2289351

PubChem CID: 15008466

Max Phase: Preclinical

Molecular Formula: C22H22N4O4

Molecular Weight: 406.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1CCc2c1nn(C)c2C(=O)NCc1ccc(Oc2ccc([N+](=O)[O-])cc2)cc1

Standard InChI:  InChI=1S/C22H22N4O4/c1-14-3-12-19-20(14)24-25(2)21(19)22(27)23-13-15-4-8-17(9-5-15)30-18-10-6-16(7-11-18)26(28)29/h4-11,14H,3,12-13H2,1-2H3,(H,23,27)

Standard InChI Key:  JDIUYPUNNJKDLL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   12.6874  -14.6851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3236  -15.1994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0096  -14.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2848  -16.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7266  -15.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7375  -15.9726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4329  -14.7292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1502  -15.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8565  -14.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5698  -15.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2756  -14.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2651  -13.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5429  -13.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8400  -13.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9667  -13.4536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6845  -13.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6920  -14.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4089  -15.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1157  -14.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1010  -13.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3835  -13.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9761  -13.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7931  -13.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0782  -13.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4414  -12.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7587  -13.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9892  -12.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8358  -15.0549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5410  -14.6308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8489  -15.8761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 23  2  0
 22  1  2  0
  2  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
 26 27  1  0
 28 29  2  0
 28 30  1  0
 19 28  1  0
M  CHG  2  28   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2289351

   2,6-dimethyl-N-[[4-(4-nitrophenoxy)phenyl]methyl]-5,6-dihydro-4H-cyclopenta[c]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: 406.44

Molecular Weight (Monoisotopic): 406.1641

AlogP: 4.10

#Rotatable Bonds: 6

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: ┄

CX Basic pKa: 1.83

CX LogP: 3.98

CX LogD: 3.98

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: -1.04

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