(E)-5-(2-hydroxy-4-((3-hydroxypropyl)(methyl)amino)benzylidene)-1-methyl-3-phenyl-2-thioxoimidazolidin-4-one

ID: ALA5286033

Max Phase: Preclinical

Molecular Formula: C21H23N3O3S

Molecular Weight: 397.50

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H23N3O3S/c1-22(11-6-12-25)17-10-9-15(19(26)14-17)13-18-20(27)24(21(28)23(18)2)16-7-4-3-5-8-16/h3-5,7-10,13-14,25-26H,6,11-12H2,1-2H3/b18-13+

Standard InChI Key:  YFDZIYYMSKMRAQ-QGOAFFKASA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -4.5404   -0.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8259    0.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1113   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3967    0.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6822   -0.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6822   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    0.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2513   -0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4585    0.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4585    0.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1731    1.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8877    0.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661    0.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4827   -0.4846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8902    0.0063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027   -0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8902   -1.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027   -2.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1278   -2.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5404   -1.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1279   -0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2209    0.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0179    0.9543    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022    1.3120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022    2.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531    1.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    0.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531    2.1364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  5  6  1  0
  7  5  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 16 15  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 16 21  1  0
 22 15  1  0
 22 23  2  0
 24 22  1  0
 24 12  1  0
 24 25  1  0
 10 26  1  0
 27  7  1  0
 26 27  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286033

   ---

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: 397.50

Molecular Weight (Monoisotopic): 397.1460

AlogP: 2.82

#Rotatable Bonds: 6

Polar Surface Area: 67.25

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.27

CX Basic pKa: 3.94

CX LogP: 2.85

CX LogD: 2.84

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -1.01

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