3-(Dimethylamino)propyl-7-fluoro-5,12-dioxo-5,12-dihydroindolizino[2,3-g]quinoline-6-carboxylate

ID: ALA4177102

PubChem CID: 145971265

Max Phase: Preclinical

Molecular Formula: C21H18FN3O4

Molecular Weight: 395.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCCOC(=O)c1c2c(n3cccc(F)c13)C(=O)c1ncccc1C2=O

Standard InChI:  InChI=1S/C21H18FN3O4/c1-24(2)9-5-11-29-21(28)15-14-18(25-10-4-7-13(22)17(15)25)20(27)16-12(19(14)26)6-3-8-23-16/h3-4,6-8,10H,5,9,11H2,1-2H3

Standard InChI Key:  UUHOHYWBEDWKTR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   14.8401  -17.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8390  -18.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5470  -18.9879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5452  -17.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2538  -17.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2572  -18.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9696  -18.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9628  -17.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6798  -17.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6815  -18.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4618  -17.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9469  -18.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4596  -18.8258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7917  -19.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6123  -19.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0996  -19.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7664  -18.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9732  -19.8056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9583  -16.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8656  -16.7813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6827  -16.7746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4511  -16.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2476  -17.5826    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.0855  -16.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9026  -16.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3054  -15.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1225  -15.3390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5340  -16.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5212  -14.6263    0.0000 C   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  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
 10 13  1  0
 12 11  2  0
 11  9  1  0
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  7 18  2  0
  8 19  2  0
 11 20  1  0
 20 21  1  0
 20 22  2  0
 17 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4177102

   ---

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: 395.39

Molecular Weight (Monoisotopic): 395.1281

AlogP: 2.36

#Rotatable Bonds: 5

Polar Surface Area: 80.98

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.06

CX LogP: 1.87

CX LogD: 1.13

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -0.77

References

1. Yu Q, Yang H, Zhu TW, Yu LM, Chen JW, Gu LQ, Huang ZS, An LK..  (2018)  Synthesis, cytotoxicity and structure-activity relationship of indolizinoquinolinedione derivatives as DNA topoisomerase IB catalytic inhibitors.,  152  [PMID:29705710] [10.1016/j.ejmech.2018.04.040]

Source

Source(1):

• Scientific Literature