(Z)-2-(4-fluorobenzylidene)-4,6-dihydroxybenzofuran-3(2H)-one

ID: ALA1814451

Chembl Id: CHEMBL1814451

PubChem CID: 53392683

Max Phase: Preclinical

Molecular Formula: C15H9FO4

Molecular Weight: 272.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccc(F)cc2)Oc2cc(O)cc(O)c21

Standard InChI:  InChI=1S/C15H9FO4/c16-9-3-1-8(2-4-9)5-13-15(19)14-11(18)6-10(17)7-12(14)20-13/h1-7,17-18H/b13-5-

Standard InChI Key:  AVESZKUTVADLAH-ACAGNQJTSA-N

Alternative Forms

1. Parent:

   

   ALA1814451

   (2Z)-2-[(4-fluorophenyl)methylene]-4,6-dihydroxy-benzofuran-3-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: 272.23

Molecular Weight (Monoisotopic): 272.0485

AlogP: 2.85

#Rotatable Bonds: 1

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.70

CX Basic pKa:

CX LogP: 3.39

CX LogD: 3.21

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.78

Np Likeness Score: 0.31

References

1. Haudecoeur R, Ahmed-Belkacem A, Yi W, Fortuné A, Brillet R, Belle C, Nicolle E, Pallier C, Pawlotsky JM, Boumendjel A..  (2011)  Discovery of naturally occurring aurones that are potent allosteric inhibitors of hepatitis C virus RNA-dependent RNA polymerase.,  54  (15): [PMID:21699179] [10.1021/jm200242p]

2. Zhang M, Xu XH, Cui Y, Xie LG, Kong CH..  (2012)  Synthesis and herbicidal potential of substituted aurones.,  68  (11): [PMID:22718431] [10.1002/ps.3339]

3. Olleik H, Yahiaoui S, Roulier B, Courvoisier-Dezord E, Perrier J, Pérès B, Hijazi A, Baydoun E, Raymond J, Boumendjel A, Maresca M, Haudecoeur R..  (2019)  Aurone derivatives as promising antibacterial agents against resistant Gram-positive pathogens.,  165  [PMID:30665143] [10.1016/j.ejmech.2019.01.022]

Source

Source(1):

• Scientific Literature