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

ID: ALA382905

Chembl Id: CHEMBL382905

PubChem CID: 11701582

Max Phase: Preclinical

Molecular Formula: C15H10O4

Molecular Weight: 254.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccccc2)Oc2cc(O)cc(O)c21

Standard InChI:  InChI=1S/C15H10O4/c16-10-7-11(17)14-12(8-10)19-13(15(14)18)6-9-4-2-1-3-5-9/h1-8,16-17H/b13-6-

Standard InChI Key:  IVVNIXHMQKNNTE-MLPAPPSSSA-N

Alternative Forms

1. Parent:

   

   ALA382905

   (2Z)-2-benzylidene-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: 254.24

Molecular Weight (Monoisotopic): 254.0579

AlogP: 2.71

#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: 3.25

CX LogD: 3.07

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.77

Np Likeness Score: 0.72

References

1. Okombi S, Rival D, Bonnet S, Mariotte AM, Perrier E, Boumendjel A..  (2006)  Discovery of benzylidenebenzofuran-3(2H)-one (aurones) as inhibitors of tyrosinase derived from human melanocytes.,  49  (1): [PMID:16392817] [10.1021/jm050715i]

2. Lee CY, Chew EH, Go ML..  (2010)  Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: synthesis, evaluation and SAR.,  45  (7): [PMID:20392544] [10.1016/j.ejmech.2010.03.023]

3. Souard F, Okombi S, Beney C, Chevalley S, Valentin A, Boumendjel A..  (2010)  1-Azaaurones derived from the naturally occurring aurones as potential antimalarial drugs.,  18  (15): [PMID:20630767] [10.1016/j.bmc.2010.06.008]

4. 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]

5. 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]

6. 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