{4-Oxo-5-[1-phenyl-meth-(Z)-ylidene]-2-thioxo-thiazolidin-3-yl}-acetic acid

ID: ALA66070

Cas Number: 1151944-57-8

PubChem CID: 1201131

Max Phase: Preclinical

Molecular Formula: C12H9NO3S2

Molecular Weight: 279.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CN1C(=O)/C(=C/c2ccccc2)SC1=S

Standard InChI:  InChI=1S/C12H9NO3S2/c14-10(15)7-13-11(16)9(18-12(13)17)6-8-4-2-1-3-5-8/h1-6H,7H2,(H,14,15)/b9-6-

Standard InChI Key:  CMANXDDFFAZWJR-TWGQIWQCSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   -2.9457    0.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5588   -0.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3872   -0.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6026   -1.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9895   -0.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610    0.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5480    0.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7633    0.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5084   -0.2966    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3166   -0.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5715    0.4880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0959    0.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0959    1.7979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562    0.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693    0.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7539    0.4459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7977   -0.6161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8015   -0.9640    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  2  3  1  0
  5  6  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  6  1  1  0
 10 18  2  0
  1  2  2  0
 12 13  2  0
  6  7  1  0
 11 14  1  0
  3  4  2  0
 14 15  1  0
  7  8  2  0
  8  9  1  0
 15 16  1  0
 15 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA66070

   [(5Z)-5-benzylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic 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: 279.34

Molecular Weight (Monoisotopic): 279.0024

AlogP: 1.97

#Rotatable Bonds: 3

Polar Surface Area: 57.61

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.71

CX Basic pKa: ┄

CX LogP: 2.44

CX LogD: -0.86

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.68

Np Likeness Score: -1.65

References

1. Grant EB, Guiadeen D, Baum EZ, Foleno BD, Jin H, Montenegro DA, Nelson EA, Bush K, Hlasta DJ..  (2000)  The synthesis and SAR of rhodanines as novel class C beta-lactamase inhibitors.,  10  (19): [PMID:11012024] [10.1016/s0960-894x(00)00444-3]

2. Smith TK, Young BL, Denton H, Hughes DL, Wagner GK..  (2009)  First small molecular inhibitors of T. brucei dolicholphosphate mannose synthase (DPMS), a validated drug target in African sleeping sickness.,  19  (6): [PMID:19217283] [10.1016/j.bmcl.2009.01.083]

3. Zinglé C, Tritsch D, Grosdemange-Billiard C, Rohmer M..  (2014)  Catechol-rhodanine derivatives: Specific and promiscuous inhibitors of Escherichia coli deoxyxylulose phosphate reductoisomerase (DXR).,  22  (14): [PMID:24890653] [10.1016/j.bmc.2014.05.004]

4. Zhang D, Markoulides MS, Stepanovs D, Rydzik AM, El-Hussein A, Bon C, Kamps JJAG, Umland KD, Collins PM, Cahill ST, Wang DY, von Delft F, Brem J, McDonough MA, Schofield CJ..  (2018)  Structure activity relationship studies on rhodanines and derived enethiol inhibitors of metallo-β-lactamases.,  26  (11): [PMID:29655609] [10.1016/j.bmc.2018.02.043]

5. Xiang Y, Chen C, Wang WM, Xu LW, Yang KW, Oelschlaeger P, He Y..  (2018)  Rhodanine as a Potent Scaffold for the Development of Broad-Spectrum Metallo-β-lactamase Inhibitors.,  9  (4): [PMID:29670701] [10.1021/acsmedchemlett.7b00548]

Source

Source(1):

• Scientific Literature