5-(2,4,5-trifluoro-3-hydroxyphenyl)-3-(4-(thiophen-3-yl)phenyl)-1,2,4-oxadiazole

ID: ALA4866994

PubChem CID: 164619679

Max Phase: Preclinical

Molecular Formula: C18H9F3N2O2S

Molecular Weight: 374.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Oc1c(F)c(F)cc(-c2nc(-c3ccc(-c4ccsc4)cc3)no2)c1F

Standard InChI:  InChI=1S/C18H9F3N2O2S/c19-13-7-12(14(20)16(24)15(13)21)18-22-17(23-25-18)10-3-1-9(2-4-10)11-5-6-26-8-11/h1-8,24H

Standard InChI Key:  RIYSKGFVNNSQLL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   11.8891   -8.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8880   -9.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5960   -9.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3057   -9.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3029   -8.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5942   -8.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0090   -8.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1800   -9.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7587   -8.5110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3033   -7.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8920   -7.1955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0933   -7.3685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4341   -9.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8868  -10.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2948  -10.7997    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.0943  -10.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1163   -7.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4491   -8.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2613   -8.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7400   -8.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4007   -7.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5895   -7.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8762   -6.7360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2512   -6.5777    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.5532   -8.2299    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.5962   -9.5575    0.0000 F   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
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  8 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
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 10 17  1  0
 17 18  2  0
 18 19  1  0
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 20 21  1  0
 21 22  2  0
 22 17  1  0
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 20 25  1  0
 19 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4866994

   ---

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: 374.34

Molecular Weight (Monoisotopic): 374.0337

AlogP: 5.26

#Rotatable Bonds: 3

Polar Surface Area: 59.15

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.13

CX Basic pKa: ┄

CX LogP: 5.76

CX LogD: 4.50

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.50

Np Likeness Score: -1.77

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