3,5-bis(3-bromo-4-hydroxybenzylidene)-tetrahydrothiopyran-4-one

ID: ALA406574

Chembl Id: CHEMBL406574

PubChem CID: 24827670

Max Phase: Preclinical

Molecular Formula: C19H14Br2O3S

Molecular Weight: 482.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccc(O)c(Br)c2)CSC/C1=C\c1ccc(O)c(Br)c1

Standard InChI:  InChI=1S/C19H14Br2O3S/c20-15-7-11(1-3-17(15)22)5-13-9-25-10-14(19(13)24)6-12-2-4-18(23)16(21)8-12/h1-8,22-23H,9-10H2/b13-5+,14-6+

Standard InChI Key:  GNKXWUPJIPHMJA-ACFHMISVSA-N

Alternative Forms

1. Parent:

   

   ALA406574

   (3Z,5Z)-3,5-bis[(3-bromo-4-hydroxyphenyl)methylidene]thian-4-one

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: 482.19

Molecular Weight (Monoisotopic): 479.9030

AlogP: 5.41

#Rotatable Bonds: 2

Polar Surface Area: 57.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.34

CX Basic pKa: ┄

CX LogP: 6.04

CX LogD: 5.65

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.56

Np Likeness Score: -0.02

References

1. Mai A, Cheng D, Bedford MT, Valente S, Nebbioso A, Perrone A, Brosch G, Sbardella G, De Bellis F, Miceli M, Altucci L..  (2008)  epigenetic multiple ligands: mixed histone/protein methyltransferase, acetyltransferase, and class III deacetylase (sirtuin) inhibitors.,  51  (7): [PMID:18348515] [10.1021/jm701595q]

2. Bouchut A, Rotili D, Pierrot C, Valente S, Lafitte S, Schultz J, Hoglund U, Mazzone R, Lucidi A, Fabrizi G, Pechalrieu D, Arimondo PB, Skinner-Adams TS, Chua MJ, Andrews KT, Mai A, Khalife J..  (2019)  Identification of novel quinazoline derivatives as potent antiplasmodial agents.,  161  [PMID:30366254] [10.1016/j.ejmech.2018.10.041]

Source

Source(1):

• Scientific Literature