4-(4-fluorophenylthio)-7-nitrobenzo[c][1,2,5]oxadiazole

ID: ALA2430539

Chembl Id: CHEMBL2430539

PubChem CID: 2821626

Max Phase: Preclinical

Molecular Formula: C12H6FN3O3S

Molecular Weight: 291.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc(Sc2ccc(F)cc2)c2nonc12

Standard InChI:  InChI=1S/C12H6FN3O3S/c13-7-1-3-8(4-2-7)20-10-6-5-9(16(17)18)11-12(10)15-19-14-11/h1-6H

Standard InChI Key:  ZJIWLIYXWOPEDX-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2430539

   Cyto5H11

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: 291.26

Molecular Weight (Monoisotopic): 291.0114

AlogP: 3.42

#Rotatable Bonds: 3

Polar Surface Area: 82.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.59

CX LogD: 3.59

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.54

Np Likeness Score: -2.04

References

1. Kessler U, Castagnolo D, Pagano M, Deodato D, Bernardini M, Pilger B, Ranadheera C, Botta M..  (2013)  Discovery and synthesis of novel benzofurazan derivatives as inhibitors of influenza A virus.,  23  (20): [PMID:24012120] [10.1016/j.bmcl.2013.08.048]

2. Tomek P, Palmer BD, Flanagan JU, Sun C, Raven EL, Ching LM..  (2017)  Discovery and evaluation of inhibitors to the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1 (IDO1): Probing the active site-inhibitor interactions.,  126  [PMID:28011425] [10.1016/j.ejmech.2016.12.029]

3. 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]

4. Mancini RS, Barden CJ, Weaver DF, Reed MA..  (2021)  Furazans in Medicinal Chemistry.,  64  (4.0): [PMID:33569941] [10.1021/acs.jmedchem.0c01901]

Source

Source(2):

• Scientific Literature
• Winzeler Lab Plasmodium Screening Data