5-(3,4-dihydroxybenzylidene)-2-thioxothiazolidin-4-one

ID: ALA255556

Chembl Id: CHEMBL255556

Cas Number: 97852-89-6

PubChem CID: 5337713

Max Phase: Preclinical

Molecular Formula: C10H7NO3S2

Molecular Weight: 253.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=S)S/C1=C\c1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C10H7NO3S2/c12-6-2-1-5(3-7(6)13)4-8-9(14)11-10(15)16-8/h1-4,12-13H,(H,11,14,15)/b8-4-

Standard InChI Key:  WVCFNVNKWVWZFT-YWEYNIOJSA-N

Alternative Forms

1. Parent:

   

   ALA255556

   5-(3,4-Dihydroxy-benzylidene)-2-thioxo-thiazolidin-4-one

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: 253.30

Molecular Weight (Monoisotopic): 252.9867

AlogP: 1.59

#Rotatable Bonds: 1

Polar Surface Area: 69.56

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.93

CX Basic pKa: ┄

CX LogP: 2.13

CX LogD: 0.30

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.40

Np Likeness Score: -0.75

References

1. Irvine MW, Patrick GL, Kewney J, Hastings SF, MacKenzie SJ..  (2008)  Rhodanine derivatives as novel inhibitors of PDE4.,  18  (6): [PMID:18304812] [10.1016/j.bmcl.2008.01.117]

2. Mustata G, Follis AV, Hammoudeh DI, Metallo SJ, Wang H, Prochownik EV, Lazo JS, Bahar I..  (2009)  Discovery of novel Myc-Max heterodimer disruptors with a three-dimensional pharmacophore model.,  52  (5): [PMID:19215087] [10.1021/jm801278g]

3. Mendgen T, Steuer C, Klein CD..  (2012)  Privileged scaffolds or promiscuous binders: a comparative study on rhodanines and related heterocycles in medicinal chemistry.,  55  (2): [PMID:22077389] [10.1021/jm201243p]

4.  (2011)  Low molecular weight MYC-MAX inhibitors, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data