3-((4-fluorophenylsulfonyl)methyl)-5-(thiophen-2-yl)-1,2,4-oxadiazole

ID: ALA1673328

PubChem CID: 2822463

Max Phase: Preclinical

Molecular Formula: C13H9FN2O3S2

Molecular Weight: 324.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(Cc1noc(-c2cccs2)n1)c1ccc(F)cc1

Standard InChI:  InChI=1S/C13H9FN2O3S2/c14-9-3-5-10(6-4-9)21(17,18)8-12-15-13(19-16-12)11-2-1-7-20-11/h1-7H,8H2

Standard InChI Key:  ZDQZUHSSQHCPIC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   18.3777  -10.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3766  -11.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0914  -11.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8078  -11.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8050  -10.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0896  -10.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5230  -11.8299    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.2368  -11.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9519  -11.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0430  -12.6477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8502  -12.8179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2612  -12.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7086  -11.4905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0893  -12.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5689  -12.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3555  -12.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3621  -11.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5795  -11.4431    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.1042  -12.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1042  -12.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6632  -10.1793    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  2  3  1  0
  5  6  2  0
  6  1  1  0
  9 10  2  0
 11 12  1  0
 13  9  1  0
 17 18  1  0
  1  2  2  0
  4  7  1  0
 15 16  1  0
  3  4  2  0
  7  8  1  0
 14 15  2  0
 16 17  2  0
 18 14  1  0
 12 14  1  0
  8  9  1  0
  7 19  2  0
 12 13  2  0
  7 20  2  0
  4  5  1  0
  1 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1673328

   3-((4-Fluorophenylsulfonyl)methyl)-5-(thiophen-2-yl)-1,2,4-oxadiazole

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: 324.36

Molecular Weight (Monoisotopic): 324.0039

AlogP: 2.91

#Rotatable Bonds: 4

Polar Surface Area: 73.06

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.41

CX Basic pKa: ┄

CX LogP: 3.03

CX LogD: 3.03

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: -2.89

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. Antonova-Koch Y, Meister S, Abraham M, Luth MR, Ottilie S, Lukens AK, Sakata-Kato T, Vanaerschot M, Owen E, Jado JC, Maher SP, Calla J, Plouffe D, Zhong Y, Chen K, Chaumeau V, Conway AJ, McNamara CW, Ibanez M, Gagaring K, Serrano FN, Eribez K, Taggard CM, Cheung AL, Lincoln C, Ambachew B, Rouillier M, Siegel D, Nosten F, Kyle DE, Gamo FJ, Zhou Y, Llinás M, Fidock DA, Wirth DF, Burrows J, Campo B, Winzeler EA..  (2018)  Open-source discovery of chemical leads for next-generation chemoprotective antimalarials.,  362  (6419): [PMID:30523084] [10.1126/science.aat9446]

Source

Source(2):

• Scientific Literature
• Winzeler Lab Plasmodium Screening Data