5-Hydroxy-6-methoxy-1-methyl-2-(4-methoxyphenyl)-4-quinolone

ID: ALA5289185

Max Phase: Preclinical

Molecular Formula: C18H17NO4

Molecular Weight: 311.34

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cc(=O)c3c(O)c(OC)ccc3n2C)cc1

Standard InChI:  InChI=1S/C18H17NO4/c1-19-13-8-9-16(23-3)18(21)17(13)15(20)10-14(19)11-4-6-12(22-2)7-5-11/h4-10,21H,1-3H3

Standard InChI Key:  AHAAASHGZWDPAB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -2.4991   -0.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845    0.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -0.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -1.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7828   -1.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4991   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3580    0.2091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -0.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -1.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3580   -1.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3580   -2.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7828   -2.2656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3580    1.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0712    0.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0713    1.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843    1.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992    1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007    0.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7889   -0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2136   -1.4449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2136   -2.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2136    1.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2136    2.2700    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
  6 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5289185

   ---

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: 311.34

Molecular Weight (Monoisotopic): 311.1158

AlogP: 2.93

#Rotatable Bonds: 3

Polar Surface Area: 60.69

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.34

CX Basic pKa: 2.01

CX LogP: 3.11

CX LogD: 3.11

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.81

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