(E)-5-(4-hydroxybenzylidene)-3-(2-oxo-2-phenylethyl)-2-thioxothiazolidin-4-one

ID: ALA4555906

PubChem CID: 155557211

Max Phase: Preclinical

Molecular Formula: C18H13NO3S2

Molecular Weight: 355.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CN1C(=O)/C(=C\c2ccc(O)cc2)SC1=S)c1ccccc1

Standard InChI:  InChI=1S/C18H13NO3S2/c20-14-8-6-12(7-9-14)10-16-17(22)19(18(23)24-16)11-15(21)13-4-2-1-3-5-13/h1-10,20H,11H2/b16-10+

Standard InChI Key:  OSGWBOQCVIYYMT-MHWRWJLKSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   24.7262  -11.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5475  -11.0486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8060  -10.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1389   -9.7815    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.4760  -10.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2533  -11.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2503  -12.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9606  -12.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5369  -12.6886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2450  -11.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5877  -10.0163    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.7605   -9.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9533  -13.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6628  -13.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3771  -13.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3775  -12.6931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6674  -12.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0481  -10.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3409   -9.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6331  -10.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6317  -11.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3438  -11.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0528  -11.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9198  -11.4933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  1 10  2  0
  3 11  2  0
  5 12  2  0
  8 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  8  1  0
 12 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4555906

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 355.44

Molecular Weight (Monoisotopic): 355.0337

AlogP: 3.48

#Rotatable Bonds: 4

Polar Surface Area: 57.61

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.31

CX Basic pKa: ┄

CX LogP: 3.89

CX LogD: 3.89

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.52

Np Likeness Score: -1.27

References

1. Xu JF, Wang TT, Yuan Q, Duan YT, Xu YJ, Lv PC, Wang XM, Yang YS, Zhu HL..  (2019)  Discovery and development of novel rhodanine derivatives targeting enoyl-acyl carrier protein reductase.,  27  (8): [PMID:30846404] [10.1016/j.bmc.2019.02.043]

Source

Source(1):

• Scientific Literature