(E)-3-cyclohexyl-5-(4-((2-hydroxyethyl)(methyl)amino)benzylidene)-1-methyl-2-thioxoimidazolidin-4-one

ID: ALA5266063

Max Phase: Preclinical

Molecular Formula: C20H27N3O2S

Molecular Weight: 373.52

Names and Identifiers

Canonical SMILES:  CN1C(=S)N(C2CCCCC2)C(=O)/C1=C\c1ccc(N(C)CCO)cc1

Standard InChI:  InChI=1S/C20H27N3O2S/c1-21(12-13-24)16-10-8-15(9-11-16)14-18-19(25)23(20(26)22(18)2)17-6-4-3-5-7-17/h8-11,14,17,24H,3-7,12-13H2,1-2H3/b18-14+

Standard InChI Key:  ZRIXYNJXSCQFPE-NBVRZTHBSA-N

Molfile:  

 
     RDKit          2D

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   -0.6104    1.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013    0.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013    0.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6086   -0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397   -0.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397   -1.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159    1.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5306    0.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    1.3123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333    0.0064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7091    0.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    2.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1256   -0.4847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6610    0.9545    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9459   -0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710   -0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1836   -1.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710   -2.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9459   -2.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333   -1.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4689   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1836    0.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  4  3  2  0
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 19 24  1  0
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  9 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5266063

   ---

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: 373.52

Molecular Weight (Monoisotopic): 373.1824

AlogP: 2.85

#Rotatable Bonds: 5

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: ┄

CX Basic pKa: 2.88

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.64

Np Likeness Score: -0.91

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