(5Z)-5-[(2,2-d2)-1,3-benzodioxol-5-ylmethylidene]-2-(phenylamino)-3,5-dihydro-4H-imidazol-4-one

ID: ALA5199422

PubChem CID: 168291843

Max Phase: Preclinical

Molecular Formula: C17H13N3O3

Molecular Weight: 307.31

Names and Identifiers

Canonical SMILES:  [2H]C1([2H])Oc2ccc(/C=C3\N=C(Nc4ccccc4)NC3=O)cc2O1

Standard InChI:  InChI=1S/C17H13N3O3/c21-16-13(8-11-6-7-14-15(9-11)23-10-22-14)19-17(20-16)18-12-4-2-1-3-5-12/h1-9H,10H2,(H2,18,19,20,21)/b13-8-/i10D2

Standard InChI Key:  PGPHHJBZEGSUNE-AAMUNQNUSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -1.4617    0.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8730   -0.4881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3289   -1.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5708   -0.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6709    0.0577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1443   -1.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8583   -0.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5734   -1.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2874   -0.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863    0.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5711    0.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8571    0.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4881   -1.9149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8110    0.9988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6329    1.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9582    1.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7903    1.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2730    1.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9238    0.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1156    0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0728   -1.0091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0709    0.3264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5570   -0.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2730   -0.7541    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2730    0.0710    0.0000 H   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
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
  3 13  2  0
  1 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
  9 21  1  0
 10 22  1  0
 22 23  1  0
 23 21  1  0
 23 24  1  0
 23 25  1  0
M  ISO  2  24   2  25   2
M  END

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: 307.31

Molecular Weight (Monoisotopic): 307.0957

AlogP: 2.35

#Rotatable Bonds: 2

Polar Surface Area: 71.95

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.87

CX Basic pKa: 0.61

CX LogP: 2.55

CX LogD: 2.55

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: -0.45

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