3-(5-(2-hydroxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)benzoic acid

ID: ALA2011401

PubChem CID: 2408328

Max Phase: Preclinical

Molecular Formula: C17H11NO4S2

Molecular Weight: 357.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cccc(N2C(=O)/C(=C/c3ccccc3O)SC2=S)c1

Standard InChI:  InChI=1S/C17H11NO4S2/c19-13-7-2-1-4-10(13)9-14-15(20)18(17(23)24-14)12-6-3-5-11(8-12)16(21)22/h1-9,19H,(H,21,22)/b14-9-

Standard InChI Key:  GRZLHGXVUKGZAV-ZROIWOOFSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -4.2723  -10.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2734  -11.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5586  -12.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8422  -11.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8450  -10.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5604  -10.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1321  -10.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4164  -10.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3984  -11.5905    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082  -11.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1385  -11.1493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6385  -10.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3998   -9.7034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3355  -12.6062    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6863  -11.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1135  -11.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9375  -11.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3345  -11.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9013  -10.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787  -10.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2949   -9.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1196   -9.6394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -8.9577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5629   -9.5330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
 12  8  1  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
 10 14  2  0
  5  7  1  0
 11 15  1  0
  3  4  2  0
 15 16  2  0
  7  8  2  0
 16 17  1  0
  8  9  1  0
 17 18  2  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
 20 15  1  0
  2  3  1  0
 19 21  1  0
  5  6  2  0
 21 22  1  0
  9 10  1  0
 21 23  2  0
 10 11  1  0
  6 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2011401

   3-[(5Z)-5-[(2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]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: 357.41

Molecular Weight (Monoisotopic): 357.0129

AlogP: 3.50

#Rotatable Bonds: 3

Polar Surface Area: 77.84

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.90

CX Basic pKa: ┄

CX LogP: 3.98

CX LogD: 0.75

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.65

Np Likeness Score: -1.50

References

1. Brvar M, Perdih A, Hodnik V, Renko M, Anderluh G, Jerala R, Solmajer T..  (2012)  In silico discovery and biophysical evaluation of novel 5-(2-hydroxybenzylidene) rhodanine inhibitors of DNA gyrase B.,  20  (8): [PMID:22444877] [10.1016/j.bmc.2012.02.052]

2. Al-Asri J, Fazekas E, Lehoczki G, Perdih A, Görick C, Melzig MF, Gyémánt G, Wolber G, Mortier J..  (2015)  From carbohydrates to drug-like fragments: Rational development of novel α-amylase inhibitors.,  23  (20): [PMID:26395057] [10.1016/j.bmc.2015.09.007]

Source

Source(1):

• Scientific Literature