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

ID: ALA4068716

Chembl Id: CHEMBL4068716

PubChem CID: 53362017

Max Phase: Preclinical

Molecular Formula: C17H17Cl3N4O2S2

Molecular Weight: 479.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(NC(=O)CN2C(=O)/C(=C/c3c(Cl)ccc(Cl)c3Cl)SC2=S)CC1

Standard InChI:  InChI=1S/C17H17Cl3N4O2S2/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:  GTHJLNHVDYJCCB-JYRVWZFOSA-N

Alternative Forms

1. Parent:

   

   ALA4068716

   N-(4-Methylpiperazin-1-Yl)-2-[(5z)-4-Oxo-2-Thioxo-5-(2,3,6-Trichlorobenzylidene)-1,3-Thiazolidin-3-Yl]acetamide

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: 479.84

Molecular Weight (Monoisotopic): 477.9859

AlogP: 3.13

#Rotatable Bonds: 4

Polar Surface Area: 55.89

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.03

CX Basic pKa: 6.97

CX LogP: 3.16

CX LogD: 3.03

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: -1.89

References

1. Gilberg E, Gütschow M, Bajorath J..  (2018)  X-ray Structures of Target-Ligand Complexes Containing Compounds with Assay Interference Potential.,  61  (3): [PMID:29328660] [10.1021/acs.jmedchem.7b01780]

2. 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]

3. Romero E, Oueslati S, Benchekroun M, D'Hollander ACA, Ventre S, Vijayakumar K, Minard C, Exilie C, Tlili L, Retailleau P, Zavala A, Elisée E, Selwa E, Nguyen LA, Pruvost A, Naas T, Iorga BI, Dodd RH, Cariou K..  (2021)  Azetidinimines as a novel series of non-covalent broad-spectrum inhibitors of β-lactamases with submicromolar activities against carbapenemases KPC-2 (class A), NDM-1 (class B) and OXA-48 (class D).,  219  [PMID:33862516] [10.1016/j.ejmech.2021.113418]

Source

Source(1):

• Scientific Literature