(E)-5-(4-(dimethylamino)-2-hydroxybenzylidene)-1-methyl-3-phenyl-2-thioxoimidazolidin-4-one

ID: ALA5268551

Max Phase: Preclinical

Molecular Formula: C19H19N3O2S

Molecular Weight: 353.45

Names and Identifiers

Canonical SMILES:  CN1C(=S)N(c2ccccc2)C(=O)/C1=C\c1ccc(N(C)C)cc1O

Standard InChI:  InChI=1S/C19H19N3O2S/c1-20(2)15-10-9-13(17(23)12-15)11-16-18(24)22(19(25)21(16)3)14-7-5-4-6-8-14/h4-12,23H,1-3H3/b16-11+

Standard InChI Key:  LAEIDNUMTXOSSM-LFIBNONCSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    1.8181   -1.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2306   -2.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0556   -2.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4681   -1.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0556   -0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2307   -0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8181    0.0064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9942    0.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4109   -0.4846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158    0.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5302    1.3120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5302    2.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1488    0.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9457    0.9542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013    1.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6130    0.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6130    0.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230   -0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0392    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7535   -0.3416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4681    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7535   -1.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0392    0.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248    1.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248    2.1362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  6  1  2  0
  6  5  1  0
  6  7  1  0
  8  7  1  0
  8  9  2  0
 10  8  1  0
 11 10  1  0
 11 12  1  0
 13  7  1  0
 11 13  1  0
 13 14  2  0
 15 10  2  0
 16 15  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 23 19  1  0
 16 24  1  0
 24 23  2  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5268551

   ---

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: 353.45

Molecular Weight (Monoisotopic): 353.1198

AlogP: 3.06

#Rotatable Bonds: 3

Polar Surface Area: 47.02

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.27

CX Basic pKa: 3.65

CX LogP: 3.48

CX LogD: 3.47

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: -0.99

References

1. Shim S, Jeong DU, Kim H, Kim CY, Park H, Jin Y, Kim KM, Lee HJ, Kim DH, Bae YS, Choi Y..  (2022)  Discovery of a NADPH oxidase inhibitor, (E)-3-cyclohexyl-5-(4-((2-hydroxyethyl)(methyl)amino)benzylidene)-1-methyl-2-thioxoimidazolidin-4-oneone, as a novel therapeutic for Parkinson's disease.,  244  [PMID:36274279] [10.1016/j.ejmech.2022.114854]

Source

Source(1):

• Scientific Literature