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

ID: ALA5270712

Max Phase: Preclinical

Molecular Formula: C19H25N3O2S

Molecular Weight: 359.50

Names and Identifiers

Canonical SMILES:  CN1C(=S)N(C2CCCCC2)C(=O)/C1=C\c1ccc(N(C)C)cc1O

Standard InChI:  InChI=1S/C19H25N3O2S/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/h9-12,14,23H,4-8H2,1-3H3/b16-11+

Standard InChI Key:  RHINPLABJJMGEG-LFIBNONCSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -2.0397    0.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3251    1.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6133    0.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6133    0.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233   -0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7544   -0.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7544   -1.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4690    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013    1.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159    0.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305    1.3123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1493    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186    0.0064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9944    0.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305    2.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4109   -0.4847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9464    0.9545    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2312   -0.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0564   -0.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4690   -1.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562   -2.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2312   -2.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186   -1.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3251    2.1367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  3 10  1  0
 10 11  2  0
 12 11  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  0
 11 15  1  0
 12 16  1  0
 15 17  2  0
 13 18  2  0
 19 14  1  0
 19 20  1  0
 21 20  1  0
 22 21  1  0
 23 22  1  0
 19 24  1  0
 24 23  1  0
  2 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5270712

   ---

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: 359.50

Molecular Weight (Monoisotopic): 359.1667

AlogP: 3.19

#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: 9.28

CX Basic pKa: 3.65

CX LogP: 3.62

CX LogD: 3.61

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.66

Np Likeness Score: -0.69

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