(Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(4-nitrophenyl)-2-thioxothiazolidin-4-one

ID: ALA561122

PubChem CID: 5861007

Max Phase: Preclinical

Molecular Formula: C18H14N2O6S2

Molecular Weight: 418.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\SC(=S)N(c3ccc([N+](=O)[O-])cc3)C2=O)cc(OC)c1O

Standard InChI:  InChI=1S/C18H14N2O6S2/c1-25-13-7-10(8-14(26-2)16(13)21)9-15-17(22)19(18(27)28-15)11-3-5-12(6-4-11)20(23)24/h3-9,21H,1-2H3/b15-9-

Standard InChI Key:  BZGORQAAWKXLDP-DHDCSXOGSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    9.7020   -9.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9569   -9.9212    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7819   -9.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0368   -9.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3694   -8.6516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2668  -10.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9313  -11.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4162  -12.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0806  -12.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2601  -12.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7752  -12.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1108  -11.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9547  -12.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6192  -13.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9246  -13.6033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5655  -13.4308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2300  -14.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3694   -7.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6549   -7.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6549   -6.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3694   -6.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0839   -6.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0839   -7.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8215   -8.8816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9173   -8.8816    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.3694   -5.3516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6549   -4.9391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0839   -4.9391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  6  7  1  0
 10 15  1  0
  2  3  1  0
  9 16  1  0
  7  8  2  0
 16 17  1  0
  3  4  1  0
  5 18  1  0
  8  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  9 10  2  0
 20 21  2  0
  5  1  1  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
 23 18  1  0
  1  2  1  0
  4 24  2  0
 11 12  2  0
  1 25  2  0
 12  7  1  0
  3  6  2  0
 11 13  1  0
 26 27  2  0
 26 28  1  0
 21 26  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA561122

   (Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(4-nitrophenyl)-2-thioxothiazolidin-4-one

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: 418.45

Molecular Weight (Monoisotopic): 418.0293

AlogP: 3.72

#Rotatable Bonds: 5

Polar Surface Area: 102.14

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: ┄

CX LogP: 3.94

CX LogD: 3.94

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.34

Np Likeness Score: -1.35

References

1. Aiello D, Barnes MH, Biswas EE, Biswas SB, Gu S, Williams JD, Bowlin TL, Moir DT..  (2009)  Discovery, characterization and comparison of inhibitors of Bacillus anthracis and Staphylococcus aureus replicative DNA helicases.,  17  (13): [PMID:19477652] [10.1016/j.bmc.2009.05.014]

Source

Source(1):

• Scientific Literature