(Z)-2-(5-(3,4-Dihydroxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-N-hydroxyacetamide

ID: ALA3309763

PubChem CID: 102129533

Max Phase: Preclinical

Molecular Formula: C12H10N2O5S2

Molecular Weight: 326.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN1C(=O)/C(=C/c2ccc(O)c(O)c2)SC1=S)NO

Standard InChI:  InChI=1S/C12H10N2O5S2/c15-7-2-1-6(3-8(7)16)4-9-11(18)14(12(20)21-9)5-10(17)13-19/h1-4,15-16,19H,5H2,(H,13,17)/b9-4-

Standard InChI Key:  OCWLWNNESIGNST-WTKPLQERSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   14.7782  -11.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7770  -12.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4851  -12.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1948  -12.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1919  -11.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4833  -11.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0704  -11.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0690  -12.8663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8981  -11.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6073  -11.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6950  -12.4416    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.4949  -12.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9009  -11.8992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3517  -11.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8301  -13.3538    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.5181  -10.4940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7133  -11.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1961  -12.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0085  -12.3814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8666  -13.2177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4914  -13.0407    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
  1  7  1  0
  2  8  1  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 12 15  2  0
 14 16  2  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3309763

   2-[(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-hydroxyacetamide

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: 326.36

Molecular Weight (Monoisotopic): 326.0031

AlogP: 0.80

#Rotatable Bonds: 3

Polar Surface Area: 110.10

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.60

CX Basic pKa: ┄

CX LogP: 1.02

CX LogD: 1.00

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.21

Np Likeness Score: -1.11

References

1. 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]

Source

Source(1):

• Scientific Literature