3-(5-(2,3-dimethoxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoic acid

ID: ALA2323030

Cas Number: 1421702-02-4

PubChem CID: 1201262

Max Phase: Preclinical

Molecular Formula: C15H15NO5S2

Molecular Weight: 353.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(/C=C2/SC(=S)N(CCC(=O)O)C2=O)c1OC

Standard InChI:  InChI=1S/C15H15NO5S2/c1-20-10-5-3-4-9(13(10)21-2)8-11-14(19)16(15(22)23-11)7-6-12(17)18/h3-5,8H,6-7H2,1-2H3,(H,17,18)/b11-8+

Standard InChI Key:  WBJNKIGKWHXRGD-DHZHZOJOSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    3.7172  -11.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7161  -12.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4241  -13.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1338  -12.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1309  -11.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4223  -11.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4199  -10.5654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1264  -10.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0094  -11.3830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092  -10.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0080  -13.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0074  -13.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458  -14.3184    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978  -15.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4150  -15.0965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680  -14.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4457  -14.0684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1169  -15.7566    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8949  -15.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5620  -16.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0418  -17.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7089  -17.9120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8546  -17.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  1  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 16 17  2  0
 14 18  2  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2323030

   3-[(5E)-5-(2,3-dimethoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]propanoic 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: 353.42

Molecular Weight (Monoisotopic): 353.0392

AlogP: 2.38

#Rotatable Bonds: 6

Polar Surface Area: 76.07

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.70

CX Basic pKa: ┄

CX LogP: 2.36

CX LogD: -0.94

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.62

Np Likeness Score: -1.38

References

1. Zhang M, Catrow JL, Ji H..  (2013)  High-Throughput Selectivity Assays for Small-Molecule Inhibitors of β-Catenin/T-Cell Factor Protein-Protein Interactions.,  4  (2): [PMID:24900664] [10.1021/ml300367f]

2. McCoy MA, Spicer D, Wells N, Hoogewijs K, Fiedler M, Baud MGJ..  (2022)  Biophysical Survey of Small-Molecule β-Catenin Inhibitors: A Cautionary Tale.,  65  (10.0): [PMID:35581674] [10.1021/acs.jmedchem.2c00228]

Source

Source(1):

• Scientific Literature