5-Methoxy-1-methyl-2-(4-hydroxyphenyl)-4-quinolone

ID: ALA5267077

Max Phase: Preclinical

Molecular Formula: C17H15NO3

Molecular Weight: 281.31

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cc(=O)c3c(O)cccc3n2C)cc1

Standard InChI:  InChI=1S/C17H15NO3/c1-18-13-4-3-5-15(19)17(13)16(20)10-14(18)11-6-8-12(21-2)9-7-11/h3-10,19H,1-2H3

Standard InChI Key:  RTZODIXFKMIZAA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -2.8565   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1419    0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300   -0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300   -1.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1400   -1.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8565   -1.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7153    0.2073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007   -0.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007   -1.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7153   -1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7153   -2.2682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1400   -2.2674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7153    1.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7139    0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4270    1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1418    1.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4315   -0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8565    1.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8565    2.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  1  0
  9  8  2  0
 10  9  1  0
  4 10  1  0
 10 11  2  0
  5 12  1  0
  7 13  1  0
 14  8  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 18 17  1  0
 14 19  1  0
 19 18  2  0
 17 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5267077

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 281.31

Molecular Weight (Monoisotopic): 281.1052

AlogP: 2.92

#Rotatable Bonds: 2

Polar Surface Area: 51.46

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.82

CX Basic pKa: 1.69

CX LogP: 3.27

CX LogD: 3.26

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.79

Np Likeness Score: 0.27

References

1. Nhoek P, Ahn S, Pel P, Kim YM, Huh J, Kim HW, Noh M, Chin YW..  (2023)  Alkaloids and Coumarins with Adiponectin-Secretion-Promoting Activities from the Leaves of Orixa japonica.,  86  (1.0): [PMID:36529937] [10.1021/acs.jnatprod.2c00844]

Source

Source(1):

• Scientific Literature