14-(5-bromopyridin-3-yl)-7,8,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(13H)-one

ID: ALA5277629

Max Phase: Preclinical

Molecular Formula: C23H17BrN4O

Molecular Weight: 445.32

Names and Identifiers

Canonical SMILES:  O=C1c2ccccc2N(c2cncc(Br)c2)C2c3[nH]c4ccccc4c3CCN12

Standard InChI:  InChI=1S/C23H17BrN4O/c24-14-11-15(13-25-12-14)28-20-8-4-2-6-18(20)23(29)27-10-9-17-16-5-1-3-7-19(16)26-21(17)22(27)28/h1-8,11-13,22,26H,9-10H2

Standard InChI Key:  WHGFMUXACHXWMK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 34  0  0  0  0  0  0  0  0999 V2000
   -3.2308    0.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5162    1.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8044    0.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8044    0.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5145   -0.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308    0.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0197   -0.1263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5347    0.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196    1.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6839    1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1367    2.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6217    1.3811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2859    0.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7709   -0.0403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5916    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9273    0.7996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4424    1.4673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8549    2.1818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7455    0.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2308    0.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984   -0.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0788   -0.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3584   -0.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7707   -1.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3587   -2.1818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4666   -2.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8785   -1.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4703   -0.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7037   -1.4715    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  4  7  1  0
  8  7  1  0
  9  8  2  0
  3  9  1  0
  9 10  1  0
 11 10  1  0
 12 11  1  0
 13 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  1  0
 17 18  2  0
 16 19  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 15 22  1  0
 23 14  1  0
 24 23  2  0
 25 24  1  0
 26 25  2  0
 27 26  1  0
 28 27  2  0
 23 28  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5277629

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 445.32

Molecular Weight (Monoisotopic): 444.0586

AlogP: 5.17

#Rotatable Bonds: 1

Polar Surface Area: 52.23

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.58

CX LogP: 4.42

CX LogD: 4.42

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.44

Np Likeness Score: -0.41

References

1. Hao X, Deng J, Zhang H, Liang Z, Lei F, Wang Y, Yang X, Wang Z..  (2021)  Design, synthesis and bioactivity evaluation of novel N-phenyl-substituted evodiamine derivatives as potent anti-tumor agents.,  55  [PMID:34990980] [10.1016/j.bmc.2021.116595]

Source

Source(1):

• Scientific Literature