3-((5-(5-chloro-4-hydroxy-2-methoxybenzylidene)-3-methyl-4-oxothiazolidin-2-ylidene)amino)benzoic acid

ID: ALA212225

PubChem CID: 44413855

Max Phase: Preclinical

Molecular Formula: C19H15ClN2O5S

Molecular Weight: 418.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(O)c(Cl)cc1/C=C1\S/C(=N/c2cccc(C(=O)O)c2)N(C)C1=O

Standard InChI:  InChI=1S/C19H15ClN2O5S/c1-22-17(24)16(8-11-7-13(20)14(23)9-15(11)27-2)28-19(22)21-12-5-3-4-10(6-12)18(25)26/h3-9,23H,1-2H3,(H,25,26)/b16-8-,21-19+

Standard InChI Key:  ICPWURUZEGNJQW-AYINJXBPSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    1.8780  -12.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0507  -12.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6266  -13.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285  -14.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8590  -14.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2794  -13.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1983  -13.5950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5993  -12.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2490  -12.1229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8531  -11.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5744  -11.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4156  -12.7716    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2989  -11.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0029  -11.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7269  -11.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4304  -12.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4103  -12.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6808  -13.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9803  -12.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7536  -10.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607  -11.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6574  -14.0761    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.1137  -13.2882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7467  -10.7773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4709  -10.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3029  -12.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1278  -12.2180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016  -11.4843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 13 14  1  0
  3  7  1  0
 14 15  2  0
  3  4  2  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
  8  9  1  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  4  5  1  0
 10 20  2  0
  2  3  1  0
  9 21  1  0
  5  6  2  0
 18 22  1  0
  9 10  1  0
 17 23  1  0
 10 11  1  0
 15 24  1  0
 11 12  1  0
 24 25  1  0
 12  8  1  0
  6  1  1  0
 11 13  2  0
 26 27  1  0
 26 28  2  0
  1 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA212225

   3-[[(5Z)-5-[(5-chloro-4-hydroxy-2-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]amino]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: 418.86

Molecular Weight (Monoisotopic): 418.0390

AlogP: 3.99

#Rotatable Bonds: 4

Polar Surface Area: 99.43

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.89

CX Basic pKa: 2.57

CX LogP: 3.71

CX LogD: 0.55

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.73

Np Likeness Score: -1.09

References

1. Dayam R, Aiello F, Deng J, Wu Y, Garofalo A, Chen X, Neamati N..  (2006)  Discovery of small molecule integrin alphavbeta3 antagonists as novel anticancer agents.,  49  (15): [PMID:16854058] [10.1021/jm051296s]

Source

Source(1):

• Scientific Literature