3-(1H-Benzo[d]imidazol-6-yl)-5-(4-fluorophenyl)-1,2,4-oxadiazole

ID: ALA3586646

Chembl Id: CHEMBL3586646

PubChem CID: 122180503

Max Phase: Preclinical

Molecular Formula: C15H9FN4O

Molecular Weight: 280.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1ccc(-c2nc(-c3ccc4nc[nH]c4c3)no2)cc1

Standard InChI:  InChI=1S/C15H9FN4O/c16-11-4-1-9(2-5-11)15-19-14(20-21-15)10-3-6-12-13(7-10)18-8-17-12/h1-8H,(H,17,18)

Standard InChI Key:  LBOBFSYTLJJUGA-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3586646

   ---

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: 280.26

Molecular Weight (Monoisotopic): 280.0760

AlogP: 3.42

#Rotatable Bonds: 2

Polar Surface Area: 67.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.77

CX Basic pKa: 5.31

CX LogP: 3.64

CX LogD: 3.64

Aromatic Rings: 4

Heavy Atoms: 21

QED Weighted: 0.61

Np Likeness Score: -1.94

References

1. Xu LL, Zhu JF, Xu XL, Zhu J, Li L, Xi MY, Jiang ZY, Zhang MY, Liu F, Lu MC, Bao QC, Li Q, Zhang C, Wei JL, Zhang XJ, Zhang LS, You QD, Sun HP..  (2015)  Discovery and Modification of in Vivo Active Nrf2 Activators with 1,2,4-Oxadiazole Core: Hits Identification and Structure-Activity Relationship Study.,  58  (14): [PMID:26111355] [10.1021/acs.jmedchem.5b00170]

2. Xu LL, Wu YF, Wang L, Li CC, Li L, Di B, You QD, Jiang ZY..  (2018)  Structure-activity and structure-property relationships of novel Nrf2 activators with a 1,2,4-oxadiazole core and their therapeutic effects on acetaminophen (APAP)-induced acute liver injury.,  157  [PMID:30196061] [10.1016/j.ejmech.2018.08.071]

3. Tran KT, Pallesen JS, Solbak SMØ, Narayanan D, Baig A, Zang J, Aguayo-Orozco A, Carmona RMC, Garcia AD, Bach A..  (2019)  A Comparative Assessment Study of Known Small-Molecule Keap1-Nrf2 Protein-Protein Interaction Inhibitors: Chemical Synthesis, Binding Properties, and Cellular Activity.,  62  (17): [PMID:31411465] [10.1021/acs.jmedchem.9b00723]

4. Lin H, Qiao Y, Yang H, Li Q, Chen Y, Qu W, Liu W, Feng F, Sun H..  (2020)  Design and evaluation of Nrf2 activators with 1,3,4-oxa/thiadiazole core as neuro-protective agents against oxidative stress in PC-12 cells.,  30  (2): [PMID:31859162] [10.1016/j.bmcl.2019.126853]

5. Dai Z, An LY, Chen XY, Yang F, Zhao N, Li CC, Ren R, Li BY, Tao WY, Li P, Jiang C, Yan F, Jiang ZY, You QD, Di B, Xu LL..  (2022)  Target Fishing Reveals a Novel Mechanism of 1,2,4-Oxadiazole Derivatives Targeting Rpn6, a Subunit of 26S Proteasome.,  65  (6.0): [PMID:35253427] [10.1021/acs.jmedchem.1c02210]

Source

Source(1):

• Scientific Literature