1-{5-[4-(5-Ethyl-[1,2,4]oxadiazol-3-yl)-phenoxy]-3-methyl-pentyl}-3-pyridin-4-yl-imidazolidin-2-one

ID: ALA195749

PubChem CID: 5278485

Max Phase: Preclinical

Molecular Formula: C24H29N5O3

Molecular Weight: 435.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1nc(-c2ccc(OCCC(C)CCN3CCN(c4ccncc4)C3=O)cc2)no1

Standard InChI:  InChI=1S/C24H29N5O3/c1-3-22-26-23(27-32-22)19-4-6-21(7-5-19)31-17-11-18(2)10-14-28-15-16-29(24(28)30)20-8-12-25-13-9-20/h4-9,12-13,18H,3,10-11,14-17H2,1-2H3

Standard InChI Key:  JQPXDPNYNDNAMJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    1.0542   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292   -3.4500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -0.2875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0042   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8792   -2.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8875   -0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3042   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -3.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833   -3.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2917   -1.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417   -1.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6875   -3.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5667   -1.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8667   -2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3250   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5792   -2.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -2.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250   -4.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2167    0.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7292   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0417    0.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4 11  1  0
  5  4  2  0
  6  1  1  0
  7  3  2  0
  8  5  1  0
  9  2  1  0
 10  2  1  0
 11 17  2  0
 12  1  2  0
 13  6  1  0
 14  6  1  0
 15 27  1  0
 16 21  2  0
 17 22  1  0
 18 24  1  0
 19 10  2  0
 20 10  1  0
 21 18  1  0
 22 18  2  0
 23 14  1  0
 24 25  1  0
 25 30  1  0
 26 19  1  0
 27 20  2  0
 28  7  1  0
 29 23  1  0
 30 29  1  0
 31 28  1  0
 32 29  1  0
  9 13  1  0
 26 15  2  0
 16 11  1  0
  8  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA195749

   1-[5-[4-(5-Ethyl-1,2,4-oxadiazol-3-yl)phenoxy]-3-methyl-pentyl]-3-(4-pyridyl)imidazolidin-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: 435.53

Molecular Weight (Monoisotopic): 435.2270

AlogP: 4.43

#Rotatable Bonds: 10

Polar Surface Area: 84.59

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.48

CX LogP: 3.85

CX LogD: 3.85

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.47

Np Likeness Score: -1.62

References

1. Chang CS, Lin YT, Shih SR, Lee CC, Lee YC, Tai CL, Tseng SN, Chern JH..  (2005)  Design, synthesis, and antipicornavirus activity of 1-[5-(4-arylphenoxy)alkyl]-3-pyridin-4-ylimidazolidin-2-one derivatives.,  48  (10): [PMID:15887961] [10.1021/jm050033v]

2. Egorova A, Ekins S, Schmidtke M, Makarov V..  (2019)  Back to the future: Advances in development of broad-spectrum capsid-binding inhibitors of enteroviruses.,  178  [PMID:31226653] [10.1016/j.ejmech.2019.06.008]

Source

Source(1):

• Scientific Literature