3-((Z)-((Z)-3-ethyl-5-(2-(2-methoxy-2-oxoethoxy)benzylidene)-4-oxothiazolidin-2-ylidene)amino)benzoic acid

ID: ALA2418562

Chembl Id: CHEMBL2418562

PubChem CID: 71818598

Max Phase: Preclinical

Molecular Formula: C22H20N2O6S

Molecular Weight: 440.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1C(=O)/C(=C/c2ccccc2OCC(=O)OC)S/C1=N\c1cccc(C(=O)O)c1

Standard InChI:  InChI=1S/C22H20N2O6S/c1-3-24-20(26)18(12-14-7-4-5-10-17(14)30-13-19(25)29-2)31-22(24)23-16-9-6-8-15(11-16)21(27)28/h4-12H,3,13H2,1-2H3,(H,27,28)/b18-12-,23-22-

Standard InChI Key:  WHQHTBZYAZZZMH-YPTZCYRCSA-N

Alternative Forms

1. Parent:

   

   ALA2418562

   3-[[(5Z)-3-ethyl-5-[[2-(2-methoxy-2-oxoethoxy)phenyl]methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]amino]benzoic acid

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: 440.48

Molecular Weight (Monoisotopic): 440.1042

AlogP: 3.56

#Rotatable Bonds: 7

Polar Surface Area: 105.50

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.88

CX Basic pKa: 2.52

CX LogP: 3.41

CX LogD: 0.37

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.52

Np Likeness Score: -1.53

References

1. Poyraz O, Jeankumar VU, Saxena S, Schnell R, Haraldsson M, Yogeeswari P, Sriram D, Schneider G..  (2013)  Structure-guided design of novel thiazolidine inhibitors of O-acetyl serine sulfhydrylase from Mycobacterium tuberculosis.,  56  (16): [PMID:23879381] [10.1021/jm400710k]

Source

Source(1):

• Scientific Literature