Ethyl-8-(3-(dimethylamino)propanamido)-5,12-dioxo-5,12-dihydroindolizino[2,3-g]quinoline-6-carboxylate

ID: ALA4173330

PubChem CID: 145949510

Max Phase: Preclinical

Molecular Formula: C23H22N4O5

Molecular Weight: 434.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1c2c(n3ccc(NC(=O)CCN(C)C)cc13)C(=O)c1ncccc1C2=O

Standard InChI:  InChI=1S/C23H22N4O5/c1-4-32-23(31)17-15-12-13(25-16(28)8-10-26(2)3)7-11-27(15)20-18(17)21(29)14-6-5-9-24-19(14)22(20)30/h5-7,9,11-12H,4,8,10H2,1-3H3,(H,25,28)

Standard InChI Key:  NJLHHDSIGNXSCF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    9.1610   -2.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1599   -3.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8679   -3.7708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8661   -2.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5748   -2.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5781   -3.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2905   -3.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2837   -2.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0007   -2.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0024   -3.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7827   -2.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2678   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7805   -3.6088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1127   -4.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9332   -4.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4205   -3.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0873   -3.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2942   -4.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2793   -1.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1865   -1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0037   -1.5575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7721   -0.8599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4181   -2.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2352   -2.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2336   -3.7805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6450   -4.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4622   -4.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2393   -5.1959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8736   -5.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6908   -5.1861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1023   -5.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0966   -4.4768    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
 21 23  1  0
 23 24  1  0
 16 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4173330

   ---

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: 434.45

Molecular Weight (Monoisotopic): 434.1590

AlogP: 2.18

#Rotatable Bonds: 6

Polar Surface Area: 110.08

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.81

CX Basic pKa: 9.15

CX LogP: 1.37

CX LogD: -0.38

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -0.85

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