3-Fluoro-5-oxo-2-piperazin-1-yl-5H-7-oxa-11b-aza-benzo[c]fluorene-6-carboxylic acid

ID: ALA293053

PubChem CID: 10809850

Max Phase: Preclinical

Molecular Formula: C20H16FN3O4

Molecular Weight: 381.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1c(=O)c2cc(F)c(N3CCNCC3)cc2n2c1oc1ccccc12

Standard InChI:  InChI=1S/C20H16FN3O4/c21-12-9-11-14(10-15(12)23-7-5-22-6-8-23)24-13-3-1-2-4-16(13)28-19(24)17(18(11)25)20(26)27/h1-4,9-10,22H,5-8H2,(H,26,27)

Standard InChI Key:  BVMNBCFZDUSZQL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    3.5167   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -2.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -0.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -2.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6500   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6500   -1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625   -2.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917    0.0583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4958   -3.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292    0.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625   -0.7792    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -1.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -3.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4958   -2.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250   -4.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500   -4.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  1  0
  5  6  1  0
  6  3  1  0
  7  1  1  0
  8  4  2  0
  9  2  1  0
 10  8  1  0
 11  5  2  0
 12  3  1  0
 13  7  1  0
 14 11  1  0
 15 10  1  0
 16  6  2  0
 17 25  1  0
 18 12  2  0
 19 14  1  0
 20 12  1  0
 21 15  1  0
 22 15  1  0
 23  9  1  0
 24 13  1  0
 25 22  1  0
 26 21  1  0
 27 23  2  0
 28 24  2  0
 13  9  2  0
  4  5  1  0
 27 28  1  0
 10 14  2  0
 26 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA293053

   3-Fluoro-5-oxo-2-piperazin-1-yl-[1,3]benzoxazolo[3,2-a]quinoline-6-carboxylic acid

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: 381.36

Molecular Weight (Monoisotopic): 381.1125

AlogP: 2.45

#Rotatable Bonds: 2

Polar Surface Area: 87.19

Molecular Species: ZWITTERION

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.64

CX Basic pKa: 8.67

CX LogP: 0.37

CX LogD: 0.37

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.55

Np Likeness Score: -0.53

References

1. Kim DH, Chung SJ, Yeon SW.  (1995)  3-Fluoro-2-(4-methylpiperazin-1-yl)-5,12-dihydro-5-oxobenzoxazolo[3,2-a]quinoline-6-carboxylic acid: Synthesis and In vitro cytotoxic activity,  5  (17): [10.1016/0960-894X(95)00338-T]

Source

Source(1):

• Scientific Literature