(S)-5-(1-amino-2-(4-hydroxyphenyl)ethyl)-3-(4-(thiophen-3-yl)phenyl)-1,2,4-oxadiazole

ID: ALA4877213

PubChem CID: 164626591

Max Phase: Preclinical

Molecular Formula: C20H17N3O2S

Molecular Weight: 363.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N[C@@H](Cc1ccc(O)cc1)c1nc(-c2ccc(-c3ccsc3)cc2)no1

Standard InChI:  InChI=1S/C20H17N3O2S/c21-18(11-13-1-7-17(24)8-2-13)20-22-19(23-25-20)15-5-3-14(4-6-15)16-9-10-26-12-16/h1-10,12,18,24H,11,21H2/t18-/m0/s1

Standard InChI Key:  CXNSALDJTWMBNH-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

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    2.6695  -16.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6684  -17.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3832  -18.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0997  -17.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0968  -16.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3813  -16.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8097  -16.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9536  -18.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5666  -16.8430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1165  -16.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7012  -15.5149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8948  -15.6896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2005  -17.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6480  -18.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600  -19.1537    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8671  -18.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9373  -16.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2757  -17.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4196  -15.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5044  -16.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0919  -17.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5044  -17.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3294  -17.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7419  -17.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3294  -16.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5669  -17.1437    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
 10 17  1  0
 17 18  1  0
 21 18  1  0
 17 19  1  1
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 20 25  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4877213

   ---

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: 363.44

Molecular Weight (Monoisotopic): 363.1041

AlogP: 4.41

#Rotatable Bonds: 5

Polar Surface Area: 85.17

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.21

CX Basic pKa: 7.14

CX LogP: 4.74

CX LogD: 4.54

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -1.35

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