5-Methoxy-3-(4-phenoxyphenyl)-1,3,4-oxadiazol-2(3H)-one

ID: ALA2171700

Chembl Id: CHEMBL2171700

PubChem CID: 18184754

Max Phase: Preclinical

Molecular Formula: C15H12N2O4

Molecular Weight: 284.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1nn(-c2ccc(Oc3ccccc3)cc2)c(=O)o1

Standard InChI:  InChI=1S/C15H12N2O4/c1-19-14-16-17(15(18)21-14)11-7-9-13(10-8-11)20-12-5-3-2-4-6-12/h2-10H,1H3

Standard InChI Key:  YAKCIFSNRAIAJM-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2171700

   5-Methoxy-3-(4-phenoxyphenyl)-1,3,4-oxadiazol-2-one

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: 284.27

Molecular Weight (Monoisotopic): 284.0797

AlogP: 2.63

#Rotatable Bonds: 4

Polar Surface Area: 66.49

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.78

CX LogD: 3.78

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.74

Np Likeness Score: -0.87

References

1. Point V, Pavan Kumar KV, Marc S, Delorme V, Parsiegla G, Amara S, Carrière F, Buono G, Fotiadu F, Canaan S, Leclaire J, Cavalier JF..  (2012)  Analysis of the discriminative inhibition of mammalian digestive lipases by 3-phenyl substituted 1,3,4-oxadiazol-2(3H)-ones.,  58  [PMID:23153815] [10.1016/j.ejmech.2012.10.040]

2. Holtfrerich A, Hanekamp W, Lehr M..  (2013)  (4-Phenoxyphenyl)tetrazolecarboxamides and related compounds as dual inhibitors of fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL).,  63  [PMID:23455058] [10.1016/j.ejmech.2013.01.050]

3. Kiss LE, Ferreira HS, Beliaev A, Torrao L, Bonifacio MJ, Learmonth DA.  (2011)  Design, synthesis, and structureactivity relationships of 1,3,4-oxadiazol-2(3H)-ones as novel FAAH inhibitors,  2  (9): [10.1039/C1MD00136A]

4. Aida J, Fushimi M, Kusumoto T, Sugiyama H, Arimura N, Ikeda S, Sasaki M, Sogabe S, Aoyama K, Koike T..  (2018)  Design, Synthesis, and Evaluation of Piperazinyl Pyrrolidin-2-ones as a Novel Series of Reversible Monoacylglycerol Lipase Inhibitors.,  61  (20): [PMID:30251836] [10.1021/acs.jmedchem.8b00824]

5. Point V,Bénarouche A,Zarrillo J,Guy A,Magnez R,Fonseca L,Raux B,Leclaire J,Buono G,Fotiadu F,Durand T,Carrière F,Vaysse C,Couëdelo L,Cavalier JF.  (2016)  Slowing down fat digestion and absorption by an oxadiazolone inhibitor targeting selectively gastric lipolysis.,  123  [PMID:27543878] [10.1016/j.ejmech.2016.08.009]

6. Afzal O,Akhtar MS,Kumar S,Ali MR,Jaggi M,Bawa S.  (2016)  Hit to lead optimization of a series of N-[4-(1,3-benzothiazol-2-yl)phenyl]acetamides as monoacylglycerol lipase inhibitors with potential anticancer activity.,  121  [PMID:27267002] [10.1016/j.ejmech.2016.05.038]

7. Cavalier JF, Spilling CD, Durand T, Camoin L, Canaan S..  (2021)  Lipolytic enzymes inhibitors: A new way for antibacterial drugs discovery.,  209  [PMID:33071055] [10.1016/j.ejmech.2020.112908]

Source

Source(1):

• Scientific Literature