5-Amino-1-[4-(2,6-dichloro-benzoyl)-benzyl]-1H-[1,2,3]triazole-4-carboxylic acid amide

ID: ALA319935

PubChem CID: 13649666

Max Phase: Preclinical

Molecular Formula: C17H13Cl2N5O2

Molecular Weight: 390.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1nnn(Cc2ccc(C(=O)c3c(Cl)cccc3Cl)cc2)c1N

Standard InChI:  InChI=1S/C17H13Cl2N5O2/c18-11-2-1-3-12(19)13(11)15(25)10-6-4-9(5-7-10)8-24-16(20)14(17(21)26)22-23-24/h1-7H,8,20H2,(H2,21,26)

Standard InChI Key:  WAUOJXWDROTZNF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -0.5333   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333   -1.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083   -1.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -1.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -0.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1000   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583   -0.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792   -4.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -4.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583   -1.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -3.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5375   -0.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500   -3.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083    0.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -2.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -4.2125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0542   -4.2167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -5.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  5  2  0
  5  1  1  0
  6  7  1  0
  7 10  1  0
  8  1  1  0
  9  3  1  0
 10 16  2  0
 11  6  2  0
 12  6  1  0
 13  2  1  0
 14  7  2  0
 15  8  2  0
 16 23  1  0
 17 22  2  0
 18  8  1  0
 19  9  1  0
 20 12  1  0
 21 11  1  0
 22 19  1  0
 23 19  2  0
 24 25  1  0
 25 12  2  0
 26 11  1  0
  3  4  1  0
 17 10  1  0
 26 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA319935

   5-Amino-1-(4-[2,6-dichlorobenzoyl]benzyl)-1,2,3-triazole-4-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: 390.23

Molecular Weight (Monoisotopic): 389.0446

AlogP: 2.55

#Rotatable Bonds: 5

Polar Surface Area: 116.89

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.08

CX Basic pKa: 0.38

CX LogP: 3.56

CX LogD: 3.56

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.65

Np Likeness Score: -1.64

References

1. Bochis RJ, Chabala JC, Harris E, Peterson LH, Barash L, Beattie T, Brown JE, Graham DW, Waksmunski FS, Tischler M..  (1991)  Benzylated 1,2,3-triazoles as anticoccidiostats.,  34  (9): [PMID:1895303] [10.1021/jm00113a024]

Source

Source(1):

• Scientific Literature