(5Z)-5-(1,3-Benzodioxol-5-ylmethylene)-3-methyl-2-(propylthio)-3,5-dihydro-4H-imidazol-4-one

ID: ALA5194491

PubChem CID: 168289232

Max Phase: Preclinical

Molecular Formula: C15H16N2O3S

Molecular Weight: 304.37

Names and Identifiers

Canonical SMILES:  CCCSC1=N/C(=C\c2ccc3c(c2)OCO3)C(=O)N1C

Standard InChI:  InChI=1S/C15H16N2O3S/c1-3-6-21-15-16-11(14(18)17(15)2)7-10-4-5-12-13(8-10)20-9-19-12/h4-5,7-8H,3,6,9H2,1-2H3/b11-7-

Standard InChI Key:  UXIAMCZUNQBRTJ-XFFZJAGNSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -1.3604    0.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7728   -0.4809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1956   -1.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4535   -0.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5359    0.0412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2611   -1.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9757   -0.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6903   -1.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049   -0.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1744   -1.0307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6692   -0.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1744    0.3160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049    0.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6903    0.4809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9757    0.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3879   -1.9102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5698   -0.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903    0.9756    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5148    1.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8446    1.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6692    1.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  2  0
  4  6  2  0
  6  7  1  0
  8  7  1  0
  9  8  2  0
 10  9  1  0
 11 10  1  0
 12 11  1  0
  9 13  1  0
 12 13  1  0
 13 14  2  0
  7 15  2  0
 15 14  1  0
  3 16  2  0
  2 17  1  0
  1 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5194491

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 304.37

Molecular Weight (Monoisotopic): 304.0882

AlogP: 2.73

#Rotatable Bonds: 3

Polar Surface Area: 51.13

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.81

Np Likeness Score: -0.72

References

1. Tahtouh T, Durieu E, Villiers B, Bruyère C, Nguyen TL, Fant X, Ahn KH, Khurana L, Deau E, Lindberg MF, Sévère E, Miege F, Roche D, Limanton E, L'Helgoual'ch JM, Burgy G, Guiheneuf S, Herault Y, Kendall DA, Carreaux F, Bazureau JP, Meijer L..  (2022)  Structure-Activity Relationship in the Leucettine Family of Kinase Inhibitors.,  65  (2.0): [PMID:34928152] [10.1021/acs.jmedchem.1c01141]

Source

Source(1):

• Scientific Literature