3-((Z)-((Z)-5-(4-Hydroxybenzylidene)-3-allyl-4-oxothiazolidin-2-ylidene)amino)benzoic Acid

ID: ALA2418548

Chembl Id: CHEMBL2418548

PubChem CID: 18846386

Max Phase: Preclinical

Molecular Formula: C20H16N2O4S

Molecular Weight: 380.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCN1C(=O)/C(=C/c2ccc(O)cc2)S/C1=N\c1cccc(C(=O)O)c1

Standard InChI:  InChI=1S/C20H16N2O4S/c1-2-10-22-18(24)17(11-13-6-8-16(23)9-7-13)27-20(22)21-15-5-3-4-14(12-15)19(25)26/h2-9,11-12,23H,1,10H2,(H,25,26)/b17-11-,21-20-

Standard InChI Key:  IBMPRVWUMIDHFQ-ICSPAVNMSA-N

Alternative Forms

1. Parent:

   

   ALA2418548

   3-[[(5Z)-5-[(4-hydroxyphenyl)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: 380.43

Molecular Weight (Monoisotopic): 380.0831

AlogP: 3.88

#Rotatable Bonds: 5

Polar Surface Area: 90.20

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.87

CX Basic pKa: 2.40

CX LogP: 4.05

CX LogD: 0.97

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -1.17

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