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

ID: ALA4523003

PubChem CID: 22425146

Max Phase: Preclinical

Molecular Formula: C18H14FNO3

Molecular Weight: 311.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc2[nH]c(-c3ccc(F)cc3)cc(=O)c2c1

Standard InChI:  InChI=1S/C18H14FNO3/c1-2-23-18(22)12-5-8-15-14(9-12)17(21)10-16(20-15)11-3-6-13(19)7-4-11/h3-10H,2H2,1H3,(H,20,21)

Standard InChI Key:  QCVYSWVGFDMXFU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    5.1163   -9.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1152  -10.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8232  -10.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8215   -9.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5301   -9.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5289  -10.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2390  -10.8947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9548  -10.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9560   -9.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2414   -9.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6575  -10.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6539  -11.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3596  -12.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0694  -11.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0691  -10.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3628  -10.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2414   -8.4272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4085   -9.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4083   -8.4362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7009   -9.6621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9931   -9.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2855   -9.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7765  -12.1276    0.0000 F   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
 14 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4523003

   Ethyl 2-(4-fluorophenyl)-4-hydroxyquinoline-6-carboxylate

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: 311.31

Molecular Weight (Monoisotopic): 311.0958

AlogP: 3.51

#Rotatable Bonds: 3

Polar Surface Area: 59.16

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.75

CX LogD: 3.75

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: -0.71

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