Ethyl 2-(3-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-6-carboxylate

ID: ALA4559684

PubChem CID: 155209424

Max Phase: Preclinical

Molecular Formula: C18H15NO4

Molecular Weight: 309.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc2[nH]c(-c3cccc(O)c3)cc(=O)c2c1

Standard InChI:  InChI=1S/C18H15NO4/c1-2-23-18(22)12-6-7-15-14(9-12)17(21)10-16(19-15)11-4-3-5-13(20)8-11/h3-10,20H,2H2,1H3,(H,19,21)

Standard InChI Key:  YSUJPYKZNRRJRD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    5.3929  -20.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917  -21.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0998  -21.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0980  -20.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8066  -20.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8054  -21.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5155  -21.9722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2313  -21.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2325  -20.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5179  -20.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9340  -21.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9304  -22.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6361  -23.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3460  -22.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3456  -21.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6393  -21.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5179  -19.5046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6851  -20.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6849  -19.5137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9775  -20.7396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2696  -20.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5620  -20.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0531  -21.5649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  8 11  1  0
 10 17  2  0
  1 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 15 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4559684

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 309.32

Molecular Weight (Monoisotopic): 309.1001

AlogP: 3.08

#Rotatable Bonds: 3

Polar Surface Area: 79.39

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.35

CX Basic pKa: ┄

CX LogP: 3.30

CX LogD: 3.30

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.73

Np Likeness Score: -0.06

References

1. Lin MS, Hong TM, Chou TH, Yang SC, Chung WC, Weng CW, Tsai ML, Cheng TR, Chen JJW, Lee TC, Wong CH, Chein RJ, Yang PC..  (2019)  4(1H)-quinolone derivatives overcome acquired resistance to anti-microtubule agents by targeting the colchicine site of β-tubulin.,  181  [PMID:31419740] [10.1016/j.ejmech.2019.111584]

Source

Source(1):

• Scientific Literature