N1-[1-[3-[4-(1H-Imidazol-1-yl)phenyl]-1-(4-nitrophenyl)-3-oxo]propyl]-pyridine-2-carboxamidrazone

ID: ALA3819602

PubChem CID: 127048365

Max Phase: Preclinical

Molecular Formula: C24H21N7O3

Molecular Weight: 455.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N/C(=N/NC(CC(=O)c1ccc(-n2ccnc2)cc1)c1ccc([N+](=O)[O-])cc1)c1ccccn1

Standard InChI:  InChI=1S/C24H21N7O3/c25-24(21-3-1-2-12-27-21)29-28-22(17-4-10-20(11-5-17)31(33)34)15-23(32)18-6-8-19(9-7-18)30-14-13-26-16-30/h1-14,16,22,28H,15H2,(H2,25,29)

Standard InChI Key:  SDVWJOULZMSBSK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511   -0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531   -1.9978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010   -3.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    2.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2029    2.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8003    1.4887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0990    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1389    1.3352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0978   -0.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3947   -1.5182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3904   -3.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0893   -3.7645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7924   -3.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7966   -1.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5023    3.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5029    5.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2041    5.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9048    5.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9042    3.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2016    7.4949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1617    8.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2400    8.0963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  7  1  0
  1  7  1  0
  4 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 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
 16 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 16  1  0
 32 33  2  0
 32 34  1  0
 29 32  1  0
M  CHG  2  32   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3819602

   ---

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: 455.48

Molecular Weight (Monoisotopic): 455.1706

AlogP: 3.40

#Rotatable Bonds: 9

Polar Surface Area: 141.33

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.25

CX LogP: 2.95

CX LogD: 2.92

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.13

Np Likeness Score: -1.61

References

1. Zampieri D, Mamolo MG, Vio L, Romano M, Skoko N, Baralle M, Pau V, De Logu A..  (2016)  Antimycobacterial activity of new N(1)-[1-[1-aryl-3-[4-(1H-imidazol-1-yl)phenyl]-3-oxo]propyl]-pyridine-2-carboxamidrazone derivatives.,  26  (14): [PMID:27241693] [10.1016/j.bmcl.2016.05.053]

Source

Source(1):

• Scientific Literature