(E)-3-(2,4-dihydroxyphenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one

ID: ALA3335590

PubChem CID: 5939029

Max Phase: Preclinical

Molecular Formula: C15H12O4

Molecular Weight: 256.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(O)cc1O)c1cccc(O)c1

Standard InChI:  InChI=1S/C15H12O4/c16-12-3-1-2-11(8-12)14(18)7-5-10-4-6-13(17)9-15(10)19/h1-9,16-17,19H/b7-5+

Standard InChI Key:  YDBQXALJOAOTJJ-FNORWQNLSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    0.4773   -5.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4762   -6.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1842   -6.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8939   -6.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8911   -5.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1825   -5.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972   -5.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3065   -5.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5942   -4.5254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0126   -5.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7219   -5.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7219   -6.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4303   -6.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1374   -6.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1317   -5.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4227   -5.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4160   -4.5131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8472   -6.9588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2318   -5.3490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 16 17  1  0
 14 18  1  0
  1 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335590

   (E)-3-(2,4-dihydroxyphenyl)-1-(3-hydroxyphenyl)prop-2-en-1-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: 256.26

Molecular Weight (Monoisotopic): 256.0736

AlogP: 2.70

#Rotatable Bonds: 3

Polar Surface Area: 77.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.47

CX Basic pKa: ┄

CX LogP: 2.98

CX LogD: 2.94

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.58

Np Likeness Score: 0.50

References

1. Balsera B, Mulet J, Fernández-Carvajal A, de la Torre-Martínez R, Ferrer-Montiel A, Hernández-Jiménez JG, Estévez-Herrera J, Borges R, Freitas AE, López MG, García-López MT, González-Muñiz R, Pérez de Vega MJ, Valor LM, Svobodová L, Sala S, Sala F, Criado M..  (2014)  Chalcones as positive allosteric modulators of α7 nicotinic acetylcholine receptors: a new target for a privileged structure.,  86  [PMID:25232969] [10.1016/j.ejmech.2014.09.039]

2. Nijampatnam B, Casals L, Zheng R, Wu H, Velu SE..  (2016)  Hydroxychalcone inhibitors of Streptococcus mutans glucosyl transferases and biofilms as potential anticaries agents.,  26  (15): [PMID:27371109] [10.1016/j.bmcl.2016.06.033]

3. Nijampatnam B, Casals L, Zheng R, Wu H, Velu SE..  (2016)  Hydroxychalcone inhibitors of Streptococcus mutans glucosyl transferases and biofilms as potential anticaries agents.,  26  (15): [PMID:27371109] [10.1016/j.bmcl.2016.06.033]

4. Trivedi-Parmar V, Jorgensen WL..  (2018)  Advances and Insights for Small Molecule Inhibition of Macrophage Migration Inhibitory Factor.,  61  (18): [PMID:29812929] [10.1021/acs.jmedchem.8b00589]

Source

Source(1):

• Scientific Literature