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

ID: ALA4168844

PubChem CID: 145955972

Max Phase: Preclinical

Molecular Formula: C25H24N4O6

Molecular Weight: 476.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1c2c(n3ccc(NC(=O)CCN4CCOCC4)cc13)C(=O)c1ncccc1C2=O

Standard InChI:  InChI=1S/C25H24N4O6/c1-2-35-25(33)19-17-14-15(27-18(30)6-8-28-10-12-34-13-11-28)5-9-29(17)22-20(19)23(31)16-4-3-7-26-21(16)24(22)32/h3-5,7,9,14H,2,6,8,10-13H2,1H3,(H,27,30)

Standard InChI Key:  VRAVNECFEXGEKW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
    0.6300  -11.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6289  -12.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3369  -12.5577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3352  -10.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0438  -11.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472  -12.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7595  -12.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7528  -10.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4697  -11.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714  -12.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2518  -11.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7368  -11.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2495  -12.3956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5817  -13.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4022  -13.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8895  -12.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5564  -11.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7632  -13.3754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7483  -10.0906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6555  -10.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4727  -10.3443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2411   -9.6468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8871  -11.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7043  -11.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026  -12.5674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1140  -13.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9312  -13.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7083  -13.9828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3427  -13.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1598  -13.9730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5673  -14.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3810  -14.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7905  -13.9707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3803  -13.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5605  -13.2624    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 35  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4168844

   ---

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: 476.49

Molecular Weight (Monoisotopic): 476.1696

AlogP: 1.95

#Rotatable Bonds: 6

Polar Surface Area: 119.31

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.81

CX Basic pKa: 6.98

CX LogP: 1.15

CX LogD: 1.01

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.42

Np Likeness Score: -1.11

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