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

ID: ALA5279528

Max Phase: Preclinical

Molecular Formula: C20H27N3O3S

Molecular Weight: 389.52

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H27N3O3S/c1-21(10-11-24)16-9-8-14(18(25)13-16)12-17-19(26)23(20(27)22(17)2)15-6-4-3-5-7-15/h8-9,12-13,15,24-25H,3-7,10-11H2,1-2H3/b17-12+

Standard InChI Key:  ODPBDBGVZVJLFJ-SFQUDFHCSA-N

Molfile:  

 
     RDKit          2D

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    2.9451   -2.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7701   -2.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1826   -1.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7701   -0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9452   -0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7087    0.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1254   -0.4846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5302    0.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2447    1.3120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2447    2.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8633    0.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.9542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158    1.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013    0.8994    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
   -0.6085   -0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0391   -0.3416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7535    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4681   -0.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1826    0.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0391   -1.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247    0.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103    1.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103    2.1362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 16 26  1  0
 26 25  2  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5279528

   ---

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: 389.52

Molecular Weight (Monoisotopic): 389.1773

AlogP: 2.55

#Rotatable Bonds: 5

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: 2.07

CX LogP: 2.93

CX LogD: 2.92

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: -0.81

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