2-(5-(4-Methoxybenzylidene)-2,4-dioxothiazolidin-3-yl)-N-(4-methoxyphenyl)acetamide

ID: ALA4554477

PubChem CID: 16632104

Max Phase: Preclinical

Molecular Formula: C20H18N2O5S

Molecular Weight: 398.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C2\SC(=O)N(CC(=O)Nc3ccc(OC)cc3)C2=O)cc1

Standard InChI:  InChI=1S/C20H18N2O5S/c1-26-15-7-3-13(4-8-15)11-17-19(24)22(20(25)28-17)12-18(23)21-14-5-9-16(27-2)10-6-14/h3-11H,12H2,1-2H3,(H,21,23)/b17-11-

Standard InChI Key:  VYTSSXJUZNXNQC-BOPFTXTBSA-N

Molfile:  

 
     RDKit          2D

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    5.5097  -22.8086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7682  -22.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011  -21.5415    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4382  -22.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6568  -21.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4865  -20.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0996  -20.4219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9257  -19.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1436  -19.3663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5351  -19.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7080  -20.7188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5457  -21.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9934  -23.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8103  -23.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2899  -24.0558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1068  -23.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5863  -24.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4025  -24.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7365  -23.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2524  -23.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4379  -23.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1436  -22.6397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2072  -23.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5493  -23.7136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0294  -24.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9716  -18.5674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5775  -18.0190    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  1  0
  4  5  1  0
  5  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
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  3 13  2  0
  2 14  1  0
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 17 18  2  0
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 22 17  1  0
 15 23  2  0
  1 24  2  0
 20 25  1  0
 25 26  1  0
 10 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4554477

   N-(4-methoxyphenyl)-2-[(5Z)-5-[(4-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 398.44

Molecular Weight (Monoisotopic): 398.0936

AlogP: 3.38

#Rotatable Bonds: 6

Polar Surface Area: 84.94

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.16

CX Basic pKa: ┄

CX LogP: 2.67

CX LogD: 2.67

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.75

Np Likeness Score: -1.67

References

1. Hassan GS, Georgey HH, Mohammed EZ, Omar FA..  (2019)  Anti-hepatitis-C virus activity and QSAR study of certain thiazolidinone and thiazolotriazine derivatives as potential NS5B polymerase inhibitors.,  184  [PMID:31604164] [10.1016/j.ejmech.2019.111747]

Source

Source(1):

• Scientific Literature