5-Methylsulfanyl-3-(4-trifluoromethoxy-phenyl)-[1,2,4]triazole-1-carboxylic acid methyl-phenyl-amide

ID: ALA131051

PubChem CID: 10476544

Max Phase: Preclinical

Molecular Formula: C18H15F3N4O2S

Molecular Weight: 408.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1nc(-c2ccc(OC(F)(F)F)cc2)nn1C(=O)N(C)c1ccccc1

Standard InChI:  InChI=1S/C18H15F3N4O2S/c1-24(13-6-4-3-5-7-13)17(26)25-16(28-2)22-15(23-25)12-8-10-14(11-9-12)27-18(19,20)21/h3-11H,1-2H3

Standard InChI Key:  RKKAABIABTWSCU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -0.8126   -0.8460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0125   -0.8460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2693   -0.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4000    0.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0652   -0.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984   -1.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1189   -1.4255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9638   -2.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500    0.1929    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0543    0.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4539   -0.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042   -2.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6628   -0.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4473   -0.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6205    0.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032    1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2212    0.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4244   -2.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097   -2.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5736   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7477   -3.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2662   -2.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0219    0.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4053    0.9547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5768    1.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7878    2.5627    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7741    1.9526    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3787    1.5673    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
  2  3  2  0
 15 16  1  0
  6  8  2  0
 16 17  2  0
 17 10  1  0
  3  4  1  0
 12 18  2  0
  5  9  1  0
 18 19  1  0
  4  5  2  0
 19 20  2  0
  3 10  1  0
 20 21  1  0
  7 11  1  0
 21 22  2  0
 22 12  1  0
  5  1  1  0
  9 23  1  0
  1  2  1  0
 15 24  1  0
  7 12  1  0
 24 25  1  0
  1  6  1  0
 25 26  1  0
 10 13  2  0
 25 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA131051

   N-methyl-5-(methylthio)-N-phenyl-3-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole-1-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: 408.40

Molecular Weight (Monoisotopic): 408.0868

AlogP: 4.67

#Rotatable Bonds: 4

Polar Surface Area: 60.25

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.29

CX LogD: 6.29

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.59

Np Likeness Score: -1.80

References

1. Ebdrup S, Sørensen LG, Olsen OH, Jacobsen P..  (2004)  Synthesis and structure-activity relationship for a novel class of potent and selective carbamoyl-triazole based inhibitors of hormone sensitive lipase.,  47  (2): [PMID:14711311] [10.1021/jm031004s]

2. Taha MO, Dahabiyeh LA, Bustanji Y, Zalloum H, Saleh S..  (2008)  Combining ligand-based pharmacophore modeling, quantitative structure-activity relationship analysis and in silico screening for the discovery of new potent hormone sensitive lipase inhibitors.,  51  (20): [PMID:18808096] [10.1021/jm800718k]

3. McConville M, Fernández J, Angulo-Barturen Í, Bahamontes-Rosa N, Ballell-Pages L, Castañeda P, de Cózar C, Crespo B, Guijarro L, Jiménez-Díaz MB, Martínez-Martínez MS, de Mercado J, Santos-Villarejo Á, Sanz LM, Frigerio M, Washbourn G, Ward SA, Nixon GL, Biagini GA, Berry NG, Blackman MJ, Calderón F, O'Neill PM..  (2015)  Carbamoyl Triazoles, Known Serine Protease Inhibitors, Are a Potent New Class of Antimalarials.,  58  (16): [PMID:26222445] [10.1021/acs.jmedchem.5b00434]

Source

Source(1):

• Scientific Literature