4,8-Dimethoxy-3-(3'-methyl-2'-oxobutyl)-2-quinolone

ID: ALA5278952

Max Phase: Preclinical

Molecular Formula: C16H19NO4

Molecular Weight: 289.33

Names and Identifiers

Canonical SMILES:  COc1c(CC(=O)C(C)C)c(=O)[nH]c2c(OC)cccc12

Standard InChI:  InChI=1S/C16H19NO4/c1-9(2)12(18)8-11-15(21-4)10-6-5-7-13(20-3)14(10)17-16(11)19/h5-7,9H,8H2,1-4H3,(H,17,19)

Standard InChI Key:  LTOAQZYUGICYOK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.8571    0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425    0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4307    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4307   -0.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407   -0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571   -0.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013   -0.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160   -0.8256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160    1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131   -0.8256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1425    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278   -0.4130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1425    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407   -1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4261   -2.0625    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  2  0
  9  8  1  0
 10  9  1  0
  4 10  1  0
  7 11  1  0
 11 12  1  0
  9 13  2  0
  8 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 16 19  1  0
  5 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5278952

   ---

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: 289.33

Molecular Weight (Monoisotopic): 289.1314

AlogP: 2.31

#Rotatable Bonds: 5

Polar Surface Area: 68.39

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.60

CX Basic pKa: ┄

CX LogP: 1.89

CX LogD: 1.89

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.92

Np Likeness Score: 0.62

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