3-((Z)-((Z)-3-allyl-5-(2-(carboxymethoxy)benzylidene)-4-oxothiazolidin-2-ylidene)amino)benzoic acid

ID: ALA2418565

Chembl Id: CHEMBL2418565

PubChem CID: 27431553

Max Phase: Preclinical

Molecular Formula: C22H18N2O6S

Molecular Weight: 438.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H18N2O6S/c1-2-10-24-20(27)18(12-14-6-3-4-9-17(14)30-13-19(25)26)31-22(24)23-16-8-5-7-15(11-16)21(28)29/h2-9,11-12H,1,10,13H2,(H,25,26)(H,28,29)/b18-12-,23-22-

Standard InChI Key:  XJLQAHHJSNLRFY-YPTZCYRCSA-N

Alternative Forms

1. Parent:

   

   ALA2418565

   3-[[(5Z)-5-[[2-(carboxymethoxy)phenyl]methylidene]-4-oxo-3-prop-2-enyl-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: 438.46

Molecular Weight (Monoisotopic): 438.0886

AlogP: 3.64

#Rotatable Bonds: 8

Polar Surface Area: 116.50

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.20

CX Basic pKa: 2.30

CX LogP: 3.49

CX LogD: -2.84

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: -1.49

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