1-(((2R,3S)-3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole

ID: ALA486029

PubChem CID: 11759286

Max Phase: Preclinical

Molecular Formula: C17H13ClFN3O

Molecular Weight: 329.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1ccc([C@]2(Cn3cncn3)O[C@H]2c2ccccc2Cl)cc1

Standard InChI:  InChI=1S/C17H13ClFN3O/c18-15-4-2-1-3-14(15)16-17(23-16,9-22-11-20-10-21-22)12-5-7-13(19)8-6-12/h1-8,10-11,16H,9H2/t16-,17-/m0/s1

Standard InChI Key:  ZMYFCFLJBGAQRS-IRXDYDNUSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    6.6357   -9.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6345  -10.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3506  -10.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0684  -10.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0655   -9.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3488   -9.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3504  -11.5695    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.7843  -10.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1986  -11.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6108  -10.7374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7785  -12.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9097  -11.8633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9078  -12.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6180  -13.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3291  -12.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3256  -11.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6148  -11.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0459  -13.0945    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.0545  -12.9428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5888  -13.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0920  -14.2805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8711  -14.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8493  -13.1783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  1  0
  5  6  2  0
  9 12  1  1
  6  1  1  0
 12 13  2  0
  1  2  2  0
 13 14  1  0
  3  7  1  0
 14 15  2  0
  9  8  1  0
 15 16  1  0
 10  9  1  0
 16 17  2  0
 17 12  1  0
  8 10  1  0
 15 18  1  0
  3  4  2  0
 11 19  1  0
 19 20  1  0
  4  5  1  0
  8  4  1  6
  2  3  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA486029

   EPOXICONAZOLE

Molecule Features

Natural Product: Yes

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: 329.76

Molecular Weight (Monoisotopic): 329.0731

AlogP: 3.74

#Rotatable Bonds: 4

Polar Surface Area: 43.24

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.00

CX LogP: 3.74

CX LogD: 3.74

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.68

Np Likeness Score: -0.78

References

1. Meyer V, Damveld RA, Arentshorst M, Stahl U, van den Hondel CA, Ram AF..  (2007)  Survival in the presence of antifungals: genome-wide expression profiling of Aspergillus niger in response to sublethal concentrations of caspofungin and fenpropimorph.,  282  (45): [PMID:17804411] [10.1074/jbc.m705856200]

2. Klix MB, Verreet JA, Beyer M..  (2007)  Comparison of the declining triazole sensitivity of Gibberella zeae and increased sensitivity achieved by advances in triazole fungicide development,  26  (4): [10.1016/j.cropro.2006.06.006]

3. Cools HJ, Bayon C, Atkins S, Lucas JA, Fraaije BA..  (2012)  Overexpression of the sterol 14α-demethylase gene (MgCYP51) in Mycosphaerella graminicola isolates confers a novel azole fungicide sensitivity phenotype.,  68  (7): [PMID:22411894] [10.1002/ps.3263]

4. Leroux P, Gredt M, Remuson F, Micoud A, Walker AS..  (2013)  Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.,  69  (1): [PMID:23073993] [10.1002/ps.3408]

Source

Source(1):

• Scientific Literature