3-Phenyl-5-(2,4-dihydroxybenzylidene)-1-methyl-2-thiohydantoin

ID: ALA3827574

PubChem CID: 127043501

Max Phase: Preclinical

Molecular Formula: C17H14N2O3S

Molecular Weight: 326.38

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H14N2O3S/c1-18-14(9-11-7-8-13(20)10-15(11)21)16(22)19(17(18)23)12-5-3-2-4-6-12/h2-10,20-21H,1H3/b14-9-

Standard InChI Key:  SZKUWDYXQPVNPJ-ZROIWOOFSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056   -3.8679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372   -5.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0391   -6.2662    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -5.2877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786   -3.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2409   -3.4780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9460   -3.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8976   -0.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019    0.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2031    1.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4999    0.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4957   -0.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5409    1.3359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    1.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508   -6.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4504   -7.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4759   -9.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989   -8.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -7.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248   -6.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  1  6  1  0
  2  8  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 13 16  1  0
 11 17  1  0
  1  9  2  0
  5 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3827574

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 326.38

Molecular Weight (Monoisotopic): 326.0725

AlogP: 2.70

#Rotatable Bonds: 2

Polar Surface Area: 64.01

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.94

CX Basic pKa: 0.21

CX LogP: 3.07

CX LogD: 3.05

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.66

Np Likeness Score: -0.44

References

1. Bae YS, Choi S, Park JJ, Joo JH, Cui M, Cho H, Lee WJ, Lee SH..  (2016)  Synthesis and biological evaluation of 3-substituted 5-benzylidene-1-methyl-2-thiohydantoins as potent NADPH oxidase (NOX) inhibitors.,  24  (18): [PMID:27407031] [10.1016/j.bmc.2016.06.056]

Source

Source(1):

• Scientific Literature