5-(2,4-Bis-trifluoromethyl-phenyl)-2-(5-chloro-2-hydroxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one

ID: ALA13855

PubChem CID: 135423093

Max Phase: Preclinical

Molecular Formula: C16H8ClF6N3O2

Molecular Weight: 423.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc(Cl)cc1-n1nc(-c2ccc(C(F)(F)F)cc2C(F)(F)F)nc1O

Standard InChI:  InChI=1S/C16H8ClF6N3O2/c17-8-2-4-12(27)11(6-8)26-14(28)24-13(25-26)9-3-1-7(15(18,19)20)5-10(9)16(21,22)23/h1-6,27H,(H,24,25,28)

Standard InChI Key:  KZJHVTHAPNKQRE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    2.6792   -1.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -1.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -0.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -0.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542   -0.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708    1.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -2.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667    0.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -0.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542    1.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542   -2.1667    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125   -1.9625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -1.9625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083    1.9208    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708    0.7583    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7208    1.4458    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6875   -3.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -4.4167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3125   -1.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  5  2  0
  5  1  1  0
  6  1  1  0
  7  8  2  0
  8  3  1  0
  9  7  1  0
 10 12  1  0
 11  7  1  0
 12 17  1  0
 13  6  2  0
 14  8  1  0
 15  6  1  0
 16  5  1  0
 17 14  2  0
 18  9  1  0
 19  9  1  0
 20  9  1  0
 21 10  1  0
 22 10  1  0
 23 10  1  0
 24 15  2  0
 25 13  1  0
 26 24  1  0
 27 25  1  0
 28 15  1  0
  3  4  1  0
 26 25  2  0
 11 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA13855

   ---

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: 423.70

Molecular Weight (Monoisotopic): 423.0209

AlogP: 5.04

#Rotatable Bonds: 2

Polar Surface Area: 71.17

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.96

CX Basic pKa: ┄

CX LogP: 6.13

CX LogD: 4.96

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: -1.04

References

1. Hewawasam P, Erway M, Thalody G, Weiner H, Boissard CG, Gribkoff VK, Meanwell NA, Lodge N, Starrett JE..  (2002)  The synthesis and structure-activity relationships of 1,3-diaryl 1,2,4-(4H)-triazol-5-ones: a new class of calcium-dependent, large conductance, potassium (maxi-K) channel opener targeted for urge urinary incontinence.,  12  (7): [PMID:11909730] [10.1016/s0960-894x(02)00099-9]

Source

Source(1):

• Scientific Literature