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

ID: ALA221810

PubChem CID: 135565394

Max Phase: Preclinical

Molecular Formula: C15H9ClF3N3O2

Molecular Weight: 355.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(-c2ccc(C(F)(F)F)cc2)nn1-c1cc(Cl)ccc1O

Standard InChI:  InChI=1S/C15H9ClF3N3O2/c16-10-5-6-12(23)11(7-10)22-14(24)20-13(21-22)8-1-3-9(4-2-8)15(17,18)19/h1-7,23H,(H,20,21,24)

Standard InChI Key:  XNRWPJIJOVVQRQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -2.3221   -2.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3210   -4.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4951   -4.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0860   -3.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5034   -2.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9348    1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9359    0.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2211    0.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5047    0.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075    1.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2229    1.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2254    2.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2333    3.3708    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4004    2.5472    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0503    2.5329    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2213   -0.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8894   -1.2465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6345   -2.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8083   -2.0310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554   -1.2447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1191   -2.6998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611   -3.3924    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5610   -3.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12  7  1  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  1  0
  3  4  2  0
 13 15  1  0
  7  8  2  0
 13 16  1  0
  9 17  1  0
 18 19  1  0
  8  9  1  0
  4  5  1  0
  9 10  2  0
  2  3  1  0
 17 18  1  0
 19 20  1  0
 20 21  1  0
 21 17  2  0
 10 11  1  0
 19 22  2  0
 20  1  1  0
  5  6  2  0
  5 23  1  0
 11 12  2  0
  2 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA221810

   ---

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: 355.70

Molecular Weight (Monoisotopic): 355.0335

AlogP: 3.61

#Rotatable Bonds: 2

Polar Surface Area: 70.91

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.72

CX Basic pKa: ┄

CX LogP: 4.35

CX LogD: 3.66

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: -1.07

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]

2. Romine JL, Martin SW, Meanwell NA, Gribkoff VK, Boissard CG, Dworetzky SI, Natale J, Moon S, Ortiz A, Yeleswaram S, Pajor L, Gao Q, Starrett JE..  (2007)  3-[(5-Chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl ]-1,3,4-oxadiazol-2(3H)-one, BMS-191011: opener of large-conductance Ca(2+)-activated potassium (maxi-K) channels, identification, solubility, and SAR.,  50  (3): [PMID:17266205] [10.1021/jm061006n]

Source

Source(1):

• Scientific Literature