5-hydroxy-1-methyl-2-phenyl-4-quinolone

ID: ALA5283771

Max Phase: Preclinical

Molecular Formula: C16H13NO2

Molecular Weight: 251.28

Names and Identifiers

Canonical SMILES:  Cn1c(-c2ccccc2)cc(=O)c2c(O)cccc21

Standard InChI:  InChI=1S/C16H13NO2/c1-17-12-8-5-9-14(18)16(12)15(19)10-13(17)11-6-3-2-4-7-11/h2-10,18H,1H3

Standard InChI Key:  PKIWUAXCGOWBKS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   -2.4998    0.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853    0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0734    0.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0734   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7836   -1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998   -0.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588    0.6198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    0.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588   -1.8557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7836   -1.8549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588    1.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0704    0.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706    1.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7835    1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4984    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    0.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881    0.2054    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
M  END

Alternative Forms

1. Parent:

   

   ALA5283771

   ---

Molecule Features

Natural Product: Yes

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: 251.28

Molecular Weight (Monoisotopic): 251.0946

AlogP: 2.91

#Rotatable Bonds: 1

Polar Surface Area: 42.23

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.82

CX Basic pKa: 1.71

CX LogP: 3.43

CX LogD: 3.41

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.72

Np Likeness Score: 0.31

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