2-(1-((5-(3-Chloro-4-nitrophenyl)-1,3,4-oxadiazol-2-yl)methyl)piperidin-4-yl)2H-benzo[d][1,2,3]triazole

ID: ALA2296612

PubChem CID: 76331267

Max Phase: Preclinical

Molecular Formula: C20H18ClN7O3

Molecular Weight: 439.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc(-c2nnc(CN3CCC(n4nc5ccccc5n4)CC3)o2)cc1Cl

Standard InChI:  InChI=1S/C20H18ClN7O3/c21-15-11-13(5-6-18(15)28(29)30)20-23-22-19(31-20)12-26-9-7-14(8-10-26)27-24-16-3-1-2-4-17(16)25-27/h1-6,11,14H,7-10,12H2

Standard InChI Key:  ZKTJTGSKUGLQLK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   18.7813  -15.6017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7968  -14.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5799  -14.5495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0466  -15.2204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5523  -15.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9785  -16.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7970  -16.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2231  -17.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8342  -17.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0198  -17.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5896  -17.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0918  -14.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3827  -14.7829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3827  -15.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6736  -16.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9645  -15.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9645  -14.7829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6736  -14.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3345  -16.9127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3161  -16.0941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5333  -15.8598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0656  -16.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5596  -17.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2424  -17.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4316  -18.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9381  -17.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2548  -16.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0400  -17.2205    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.2659  -18.6581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0828  -18.6354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8772  -19.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
  5  6  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 18  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 19 23  2  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 22 27  1  0
 23 24  1  0
 16 20  1  0
 12 13  1  0
  2 12  1  0
  8 28  1  0
 29 30  2  0
 29 31  1  0
  9 29  1  0
M  CHG  2  29   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2296612

   2-[[4-(Benzotriazol-2-yl)-1-piperidyl]methyl]-5-(3-chloro-4-nitro-phenyl)-1,3,4-oxadiazole

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: 439.86

Molecular Weight (Monoisotopic): 439.1160

AlogP: 3.88

#Rotatable Bonds: 5

Polar Surface Area: 116.01

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.16

CX LogP: 2.86

CX LogD: 2.67

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.34

Np Likeness Score: -1.83

References

1. Vankadari SR, Mandala D, Pochampalli J, Tigulla P, Valeru A, Thampu R.  (2013)  Synthesis, evaluation of antimicrobial activity, and molecular modeling of novel 2-((4-(2H-benzo[d] [1,2,3] triazol-2-yl)piperidin-1-yl)methyl)-5-substituted phenyl-1,3,4-oxadiazoles,  22  (12): [10.1007/s00044-013-0573-9]

Source

Source(1):

• Scientific Literature