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

ID: ALA130478

PubChem CID: 11210161

Max Phase: Preclinical

Molecular Formula: C13H13F3N4O2S

Molecular Weight: 346.33

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H13F3N4O2S/c1-19(2)12(21)20-11(23-3)17-10(18-20)8-4-6-9(7-5-8)22-13(14,15)16/h4-7H,1-3H3

Standard InChI Key:  FBOHEFQKBNWFPO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.0458  -16.9750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8708  -16.9750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1276  -16.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4583  -15.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7933  -16.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5600  -17.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7396  -17.5545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8946  -18.3960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4051  -16.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2539  -18.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0085  -15.9363    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.9088  -15.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5210  -16.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3054  -16.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4787  -15.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8614  -14.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0794  -15.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8366  -15.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2633  -15.1746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4349  -14.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6458  -13.5667    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.6323  -14.1767    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.2367  -14.5619    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
 12 13  2  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 12  1  0
  3 12  1  0
  3  4  1  0
 11 18  1  0
  7  9  1  0
 15 19  1  0
  4  5  2  0
 19 20  1  0
  7 10  1  0
 20 21  1  0
  5  1  1  0
 20 22  1  0
  5 11  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA130478

   N,N-dimethyl-5-(methylthio)-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: 346.33

Molecular Weight (Monoisotopic): 346.0711

AlogP: 3.10

#Rotatable Bonds: 3

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: 4.64

CX LogD: 4.64

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.80

Np Likeness Score: -1.85

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