(Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-thioxo-3-(3-(trifluoromethyl)phenyl)thiazolidin-4-one

ID: ALA561523

PubChem CID: 1310066

Max Phase: Preclinical

Molecular Formula: C19H14F3NO4S2

Molecular Weight: 441.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\SC(=S)N(c3cccc(C(F)(F)F)c3)C2=O)cc(OC)c1O

Standard InChI:  InChI=1S/C19H14F3NO4S2/c1-26-13-6-10(7-14(27-2)16(13)24)8-15-17(25)23(18(28)29-15)12-5-3-4-11(9-12)19(20,21)22/h3-9,24H,1-2H3/b15-8-

Standard InChI Key:  MASLKHTWMHYHNX-NVNXTCNLSA-N

Molfile:  

     RDKit          2D

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   -1.1898  -12.5222    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3648  -12.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1098  -11.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7773  -11.2526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1202  -13.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2154  -13.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2695  -14.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0660  -15.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1919  -14.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5275  -15.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2221  -16.2043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4189  -16.0319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833  -16.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0628   -9.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628  -10.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6748  -11.4826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2293  -11.4826    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6517   -8.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3661   -8.3651    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642   -9.4921    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.2392   -8.0632    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  6  7  1  0
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  7  8  2  0
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  3  4  1  0
  5 18  1  0
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 18 19  2  0
  4  5  1  0
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  9 10  2  0
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  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
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  3  6  2  0
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 11 13  1  0
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 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA561523

   (Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-thioxo-3-(3-(trifluoromethyl)phenyl)thiazolidin-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: 441.45

Molecular Weight (Monoisotopic): 441.0316

AlogP: 4.83

#Rotatable Bonds: 4

Polar Surface Area: 59.00

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: ┄

CX LogP: 4.88

CX LogD: 4.87

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: -1.43

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