4-(4-Fluorophenyl)-6,7-methylenedioxyquinolin-2(1H)-one

ID: ALA2420809

PubChem CID: 71770296

Max Phase: Preclinical

Molecular Formula: C16H10FNO3

Molecular Weight: 283.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1cc(-c2ccc(F)cc2)c2cc3c(cc2[nH]1)OCO3

Standard InChI:  InChI=1S/C16H10FNO3/c17-10-3-1-9(2-4-10)11-6-16(19)18-13-7-15-14(5-12(11)13)20-8-21-15/h1-7H,8H2,(H,18,19)

Standard InChI Key:  OHXPCPUWEDSACQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
   35.0729   -7.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0711   -6.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7797   -6.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7805   -7.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4890   -7.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1973   -7.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1926   -6.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4835   -6.1030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4898   -8.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7813   -8.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7826   -9.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4917  -10.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2009   -9.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1961   -8.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3649   -7.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3615   -6.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5796   -6.2648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0997   -6.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5850   -7.5932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.8978   -6.0935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4945  -11.0043    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 15  1  1  0
  1  4  2  0
  3  2  2  0
  2 16  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  3  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  5  9  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
  7 20  2  0
 12 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2420809

   8-(4-fluorophenyl)-5H-[1,3]dioxolo[4,5-g]quinolin-6-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: 283.26

Molecular Weight (Monoisotopic): 283.0645

AlogP: 3.06

#Rotatable Bonds: 1

Polar Surface Area: 51.32

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.66

CX Basic pKa: ┄

CX LogP: 2.80

CX LogD: 2.80

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.75

Np Likeness Score: -0.40

References

1. Chen YF, Lin YC, Huang PK, Chan HC, Kuo SC, Lee KH, Huang LJ..  (2013)  Design and synthesis of 6,7-methylenedioxy-4-substituted phenylquinolin-2(1H)-one derivatives as novel anticancer agents that induce apoptosis with cell cycle arrest at G2/M phase.,  21  (17): [PMID:23867385] [10.1016/j.bmc.2013.06.046]

Source

Source(1):

• Scientific Literature