2-(4-Hydroxy-phenyl)-3,7-dimethoxy-5-methyl-chromen-4-one

ID: ALA348970

PubChem CID: 14804713

Max Phase: Preclinical

Molecular Formula: C18H16O5

Molecular Weight: 312.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C)c2c(=O)c(OC)c(-c3ccc(O)cc3)oc2c1

Standard InChI:  InChI=1S/C18H16O5/c1-10-8-13(21-2)9-14-15(10)16(20)18(22-3)17(23-14)11-4-6-12(19)7-5-11/h4-9,19H,1-3H3

Standard InChI Key:  YDVWRZBDQQROKN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  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
    5.1542   -4.2292    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
    4.6292   -3.9250    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
    4.1125   -4.2292    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
    5.1500   -4.8292    0.0000 O   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
    3.5917   -3.3250    0.0000 C   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -4.8292    0.0000 C   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
    2.9167   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  3  1  0
  5  2  1  0
  6  4  1  0
  7  5  2  0
  8  6  2  0
  9  3  1  0
 10  2  2  0
 11  7  1  0
 12  8  1  0
 13  1  1  0
 14  9  2  0
 15  9  1  0
 16 17  1  0
 17 15  2  0
 18 14  1  0
 19 12  1  0
 20  7  1  0
 21 16  1  0
 22 13  1  0
 23 19  1  0
  6  5  1  0
 18 16  2  0
 12 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA348970

   4'-Hydroxy-3,7-dimethoxy-5-methyl flavone

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: 312.32

Molecular Weight (Monoisotopic): 312.0998

AlogP: 3.49

#Rotatable Bonds: 3

Polar Surface Area: 68.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.55

CX Basic pKa: ┄

CX LogP: 2.89

CX LogD: 2.86

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.80

Np Likeness Score: 0.89

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]

Source

Source(1):

• Scientific Literature