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

ID: ALA166029

Cas Number: 59259-80-2

PubChem CID: 14414499

Max Phase: Preclinical

Molecular Formula: C18H16O6

Molecular Weight: 328.32

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H16O6/c1-21-12-8-13(22-2)15-14(9-12)24-17(18(23-3)16(15)20)10-4-6-11(19)7-5-10/h4-9,19H,1-3H3

Standard InChI Key:  NGOJYRXQNKPQOD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  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
    4.6292   -3.9250    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
    4.6375   -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
    3.5917   -3.9292    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   -3.3250    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
    4.1167   -4.8292    0.0000 O   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
    7.2292   -3.0292    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
    3.0750   -3.0250    0.0000 O   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
    3.5917   -5.1292    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  2  1  0
  4  1  2  0
  5  4  1  0
  6  5  1  0
  7  3  2  0
  8  6  2  0
  9  7  1  0
 10  4  1  0
 11  2  2  0
 12  8  1  0
 13  1  1  0
 14 10  2  0
 15 10  1  0
 16  7  1  0
 17 19  1  0
 18 14  1  0
 19 15  2  0
 20 12  1  0
 21 17  1  0
 22 13  1  0
 23 16  1  0
 24 20  1  0
  6  3  1  0
 18 17  2  0
 12  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA166029

   2-(4-Hydroxyphenyl)-3,5,7-trimethoxy-4H-1-benzopyran-4-one

Molecule Features

Natural Product: Yes

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: 328.32

Molecular Weight (Monoisotopic): 328.0947

AlogP: 3.19

#Rotatable Bonds: 4

Polar Surface Area: 78.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.55

CX Basic pKa: ┄

CX LogP: 2.21

CX LogD: 2.18

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: 1.06

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