ethyl 2,5-dimethyl-6-(5-phenyl-4H-1,2,4-triazol-3-ylthio)pyrimidine-4-carboxylate

ID: ALA1673330

PubChem CID: 2746800

Max Phase: Preclinical

Molecular Formula: C17H17N5O2S

Molecular Weight: 355.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1nc(C)nc(Sc2nnc(-c3ccccc3)[nH]2)c1C

Standard InChI:  InChI=1S/C17H17N5O2S/c1-4-24-16(23)13-10(2)15(19-11(3)18-13)25-17-20-14(21-22-17)12-8-6-5-7-9-12/h5-9H,4H2,1-3H3,(H,20,21,22)

Standard InChI Key:  BQBGKCNGZDTZNA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    3.8777  -15.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8766  -16.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5914  -17.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3078  -16.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3050  -15.8463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5896  -15.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5871  -14.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5912  -17.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0230  -17.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0242  -17.9132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7368  -16.6746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4519  -17.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1657  -16.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1618  -17.0893    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4476  -16.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4541  -15.8522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6722  -15.5890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1802  -16.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6579  -16.9238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578  -16.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0464  -15.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8706  -15.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2916  -16.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8823  -16.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595  -16.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
  2 14  1  0
  6  7  1  0
 14 15  1  0
 18 19  1  0
  3  4  2  0
 16 17  1  0
  3  8  1  0
  4  9  1  0
 15 16  2  0
 17 18  2  0
 19 15  1  0
  4  5  1  0
  9 10  2  0
 20 21  2  0
  2  3  1  0
 21 22  1  0
  9 11  1  0
 22 23  2  0
  5  6  2  0
 23 24  1  0
 11 12  1  0
 24 25  2  0
 25 20  1  0
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1673330

   ethyl 2,5-dimethyl-6-(5-phenyl-4H-1,2,4-triazol-3-ylthio)pyrimidine-4-carboxylate

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: 355.42

Molecular Weight (Monoisotopic): 355.1103

AlogP: 3.21

#Rotatable Bonds: 5

Polar Surface Area: 93.65

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.79

CX Basic pKa: 1.51

CX LogP: 3.89

CX LogD: 3.77

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.55

Np Likeness Score: -1.33

References

1. King-Keller S, Li M, Smith A, Zheng S, Kaur G, Yang X, Wang B, Docampo R..  (2010)  Chemical validation of phosphodiesterase C as a chemotherapeutic target in Trypanosoma cruzi, the etiological agent of Chagas' disease.,  54  (9): [PMID:20625148] [10.1128/aac.00313-10]

2. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays