2-(2,4-Dioxo-5-(2,3,6-trichlorobenzylidene)thiazolidin-3-yl)-N-(4-methylpiperazin-1-yl)acetamide

ID: ALA4129450

PubChem CID: 145963279

Max Phase: Preclinical

Molecular Formula: C17H17Cl3N4O3S

Molecular Weight: 463.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(NC(=O)CN2C(=O)S/C(=C\c3c(Cl)ccc(Cl)c3Cl)C2=O)CC1

Standard InChI:  InChI=1S/C17H17Cl3N4O3S/c1-22-4-6-23(7-5-22)21-14(25)9-24-16(26)13(28-17(24)27)8-10-11(18)2-3-12(19)15(10)20/h2-3,8H,4-7,9H2,1H3,(H,21,25)/b13-8-

Standard InChI Key:  HGSYUTHQDDLTJN-JYRVWZFOSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    5.9916   -6.4834    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8166   -6.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0735   -5.6993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4041   -5.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7391   -5.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4029   -4.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3008   -7.1514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9544   -5.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3415   -5.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8584   -5.4453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0310   -4.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8161   -4.3848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4187   -4.0858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9887   -3.5781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7724   -3.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9462   -2.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3365   -1.9690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5499   -2.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3732   -3.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5121   -1.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577   -5.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451   -6.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1168   -7.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9064   -7.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5155   -6.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3873   -4.9327    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1605   -6.0365    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3012   -7.0510    0.0000 Cl  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
  4  6  2  0
  2  7  2  0
  5  8  2  0
  8  9  1  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
  9 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25  9  1  0
 21 26  1  0
 22 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4129450

   ---

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: 463.77

Molecular Weight (Monoisotopic): 462.0087

AlogP: 2.96

#Rotatable Bonds: 4

Polar Surface Area: 72.96

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.84

CX Basic pKa: 6.97

CX LogP: 2.27

CX LogD: 2.14

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.55

Np Likeness Score: -1.79

References

1. 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]

Source

Source(1):

• Scientific Literature