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

ID: ALA5269857

Max Phase: Preclinical

Molecular Formula: C21H29N3O2S

Molecular Weight: 387.55

Names and Identifiers

Canonical SMILES:  CCN(CC)c1ccc(/C=C2\C(=O)N(C3CCCCC3)C(=S)N2C)c(O)c1

Standard InChI:  InChI=1S/C21H29N3O2S/c1-4-23(5-2)17-12-11-15(19(25)14-17)13-18-20(26)24(21(27)22(18)3)16-9-7-6-8-10-16/h11-14,16,25H,4-10H2,1-3H3/b18-13+

Standard InChI Key:  JSMJURUWKJMZCJ-QGOAFFKASA-N

Molfile:  

 
     RDKit          2D

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    2.5881   -2.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4131   -2.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256   -1.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4131   -0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5881   -0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1755    0.0064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3515    0.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7681   -0.4847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1731    0.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8876    1.3120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8876    2.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5062    0.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031    0.9543    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4585    1.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559    0.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559    0.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9658   -0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6821    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3966   -0.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3966   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6821    0.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    1.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    2.1364    0.0000 O   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
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  8  7  1  0
  8  9  2  0
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 11 13  1  0
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 16 26  1  0
 26 25  2  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5269857

   ---

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: 387.55

Molecular Weight (Monoisotopic): 387.1980

AlogP: 3.97

#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: 9.27

CX Basic pKa: 4.51

CX LogP: 4.33

CX LogD: 4.33

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -0.77

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