3-[3-(2-Hydroxy-ethoxy)-phenyl]-1H-quinolin-2-one

ID: ALA97218

PubChem CID: 6918599

Max Phase: Preclinical

Molecular Formula: C17H15NO3

Molecular Weight: 281.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCCOc1cccc(-c2cc3ccccc3nc2O)c1

Standard InChI:  InChI=1S/C17H15NO3/c19-8-9-21-14-6-3-5-12(10-14)15-11-13-4-1-2-7-16(13)18-17(15)20/h1-7,10-11,19H,8-9H2,(H,18,20)

Standard InChI Key:  CAPTUZLISRNFKN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    3.3417   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375   -2.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -2.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2000   -1.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6292   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542   -0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6292   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9125   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  2  0
  5  1  1  0
  6  7  2  0
  7  4  1  0
  8  2  1  0
  9  5  2  0
 10  9  1  0
 11  5  1  0
 12 10  1  0
 13 18  1  0
 14 11  2  0
 15  6  1  0
 16  7  1  0
 17 14  1  0
 18 19  1  0
 19 12  1  0
 20 21  1  0
 21 16  2  0
  3  6  1  0
 17 10  2  0
 15 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA97218

   3-[3-(2-Hydroxy-ethoxy)-phenyl]-1H-quinolin-2-one

Molecule Features

Natural Product: No

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: 281.31

Molecular Weight (Monoisotopic): 281.1052

AlogP: 2.98

#Rotatable Bonds: 4

Polar Surface Area: 62.58

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.69

CX Basic pKa: 1.53

CX LogP: 3.22

CX LogD: 3.22

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.77

Np Likeness Score: -0.51

References

1. Xiao Z, Waters NC, Woodard CL, Li Z, Li PK..  (2001)  Design and synthesis of Pfmrk inhibitors as potential antimalarial agents.,  11  (21): [PMID:11597420] [10.1016/s0960-894x(01)00578-9]

2. Bhattacharjee AK, Geyer JA, Woodard CL, Kathcart AK, Nichols DA, Prigge ST, Li Z, Mott BT, Waters NC..  (2004)  A three-dimensional in silico pharmacophore model for inhibition of Plasmodium falciparum cyclin-dependent kinases and discovery of different classes of novel Pfmrk specific inhibitors.,  47  (22): [PMID:15481979] [10.1021/jm040108f]

3. Cabrera DG, Horatscheck A, Wilson CR, Basarab G, Eyermann CJ, Chibale K..  (2018)  Plasmodial Kinase Inhibitors: License to Cure?,  61  (18): [PMID:29771541] [10.1021/acs.jmedchem.8b00329]

Source

Source(1):

• Scientific Literature