7-Chloro-2-(4-hydroxy-phenyl)-3-methoxy-chromen-4-one

ID: ALA163467

PubChem CID: 14804707

Max Phase: Preclinical

Molecular Formula: C16H11ClO4

Molecular Weight: 302.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(-c2ccc(O)cc2)oc2cc(Cl)ccc2c1=O

Standard InChI:  InChI=1S/C16H11ClO4/c1-20-16-14(19)12-7-4-10(17)8-13(12)21-15(16)9-2-5-11(18)6-3-9/h2-8,18H,1H3

Standard InChI Key:  PZAXKBYPGZOMEQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    5.6750   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6750   -3.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -3.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6375   -3.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125   -3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1500   -4.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -4.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7125   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -3.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7125   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -3.0250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.7542   -2.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -4.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  6  1  0
  6  4  1  0
  7  5  2  0
  8  2  1  0
  9  6  2  0
 10  4  2  0
 11  1  1  0
 12  8  2  0
 13  8  1  0
 14 15  2  0
 15  9  1  0
 16 17  1  0
 17 13  2  0
 18 12  1  0
 19 14  1  0
 20 16  1  0
 21 11  1  0
  3  5  1  0
 18 16  2  0
 14  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA163467

   7-Chloro-2-(4-hydroxyphenyl)-3-methoxychromen-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: 302.71

Molecular Weight (Monoisotopic): 302.0346

AlogP: 3.83

#Rotatable Bonds: 2

Polar Surface Area: 59.67

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.55

CX Basic pKa: ┄

CX LogP: 3.13

CX LogD: 3.10

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.78

Np Likeness Score: 0.45

References

1. De Meyer N, Haemers A, Mishra L, Pandey HK, Pieters LA, Vanden Berghe DA, Vlietinck AJ..  (1991)  4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.,  34  (2): [PMID:1847431] [10.1021/jm00106a039]

2. Venkateswararao E, Son MJ, Sharma N, Manickam M, Boggu P, Kim YH, Woo SH, Jung SH..  (2015)  Exploration of Pharmacophore in Chrysosplenol C as Activator in Ventricular Myocyte Contraction.,  6  (7): [PMID:26191362] [10.1021/acsmedchemlett.5b00043]

Source

Source(1):

• Scientific Literature