4-(4-Oxo-3-phenyl-2-phenylimino-thiazolidin-5-ylidenemethyl)-benzoic acid

ID: ALA2297516

PubChem CID: 2254837

Max Phase: Preclinical

Molecular Formula: C23H16N2O3S

Molecular Weight: 400.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(/C=C2/S/C(=N\c3ccccc3)N(c3ccccc3)C2=O)cc1

Standard InChI:  InChI=1S/C23H16N2O3S/c26-21-20(15-16-11-13-17(14-12-16)22(27)28)29-23(24-18-7-3-1-4-8-18)25(21)19-9-5-2-6-10-19/h1-15H,(H,27,28)/b20-15+,24-23-

Standard InChI Key:  SAKYBTFUWBZKRG-MIIQOVFOSA-N

Molfile:  

     RDKit          2D

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    2.6616   -4.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587   -3.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9501   -2.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0770   -4.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9565   -3.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4295   -1.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9909   -5.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3826   -5.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5531   -6.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3313   -6.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9393   -6.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7657   -5.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5391   -2.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0214   -2.6810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8693   -1.2738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  3  4  2  0
  4  5  1  0
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 19 20  2  0
 20 15  1  0
 21 22  2  0
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 26 21  1  0
  9 21  1  0
 27 28  1  0
 27 29  2  0
 18 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2297516

   4-[(E)-(4-oxo-3-phenyl-2-phenylimino-1,3-thiazolidin-5-ylidene)methyl]benzoic acid

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: 400.46

Molecular Weight (Monoisotopic): 400.0882

AlogP: 5.19

#Rotatable Bonds: 4

Polar Surface Area: 69.97

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.07

CX Basic pKa: 0.08

CX LogP: 5.45

CX LogD: 2.33

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.61

Np Likeness Score: -1.29

References

1. Zhao D, Liu H, Zheng L, He G, Qu D, Han S.  (2013)  Synthesis of novel 4-thiazolidione derivatives as antibacterial agents against drug-resistant Staphylococcus epidermidis,  22  (8): [10.1007/s00044-012-0363-9]

Source

Source(1):

• Scientific Literature