5-((2S-4R)-1-acetyl-4-hydroxypyrrolidin-2-yl)-3-(4-(thiophen-3-yl)phenyl)-1,2,4-oxadiazole

ID: ALA4875450

PubChem CID: 164627415

Max Phase: Preclinical

Molecular Formula: C18H17N3O3S

Molecular Weight: 355.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)N1C[C@H](O)C[C@H]1c1nc(-c2ccc(-c3ccsc3)cc2)no1

Standard InChI:  InChI=1S/C18H17N3O3S/c1-11(22)21-9-15(23)8-16(21)18-19-17(20-24-18)13-4-2-12(3-5-13)14-6-7-25-10-14/h2-7,10,15-16,23H,8-9H2,1H3/t15-,16+/m1/s1

Standard InChI Key:  MKRVGSKWSIWIDZ-CVEARBPZSA-N

Molfile:  

 
     RDKit          2D

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   19.8382   -9.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8370   -9.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5451  -10.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2547   -9.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2519   -9.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5433   -8.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9581   -8.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1290  -10.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7078   -8.9485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2523   -8.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8410   -7.6329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0424   -7.8060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3831   -9.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8358  -10.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2439  -11.2372    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.0433  -11.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0653   -8.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4765   -9.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2751   -8.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3575   -8.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6097   -7.8077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4352   -7.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0393   -6.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6566   -6.7613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8845   -9.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  2  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  7  2  0
  8 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16  8  2  0
 17 10  1  1
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 19 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4875450

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 355.42

Molecular Weight (Monoisotopic): 355.0991

AlogP: 3.12

#Rotatable Bonds: 3

Polar Surface Area: 79.46

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.40

CX LogD: 2.40

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: -1.56

References

1. Potenza M, Sciarretta M, Chini MG, Saviano A, Maione F, D'Auria MV, De Marino S, Giordano A, Hofstetter RK, Festa C, Werz O, Bifulco G..  (2021)  Structure-based screening for the discovery of 1,2,4-oxadiazoles as promising hits for the development of new anti-inflammatory agents interfering with eicosanoid biosynthesis pathways.,  224  [PMID:34315041] [10.1016/j.ejmech.2021.113693]

Source

Source(1):

• Scientific Literature