Methyl 3-[(6-(3-Aminopropyl)-5,11-dioxo-6,11-dihydro-5Hindeno[1,2-c]isoquinolin-3-yl)amino]-3-oxopropanoate

ID: ALA2312571

PubChem CID: 71546517

Max Phase: Preclinical

Molecular Formula: C23H21N3O5

Molecular Weight: 419.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CC(=O)Nc1ccc2c3c(n(CCCN)c(=O)c2c1)-c1ccccc1C3=O

Standard InChI:  InChI=1S/C23H21N3O5/c1-31-19(28)12-18(27)25-13-7-8-14-17(11-13)23(30)26(10-4-9-24)21-15-5-2-3-6-16(15)22(29)20(14)21/h2-3,5-8,11H,4,9-10,12,24H2,1H3,(H,25,27)

Standard InChI Key:  WPRKQIRWRMVZPA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    5.1877   -7.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -5.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1953   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1932   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4914   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4897   -4.9570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0114    1.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5021    1.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3837    2.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7736    4.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2819    4.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4013    3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095    2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1065    3.8582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 15 20  1  0
 20 21  2  0
 20 22  1  0
 22 12  1  0
 22 23  2  0
 23  9  1  0
 14 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 29 30  1  0
 30 13  1  0
 30 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2312571

   Methyl 3-[[6-(3-aminopropyl)-5,11-dioxoindeno[1,2-c]isoquinolin-3-yl]amino]-3-oxopropanoate

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: 419.44

Molecular Weight (Monoisotopic): 419.1481

AlogP: 2.06

#Rotatable Bonds: 6

Polar Surface Area: 120.49

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.78

CX Basic pKa: 9.57

CX LogP: 0.66

CX LogD: -1.46

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.36

Np Likeness Score: -0.31

References

1. Conda-Sheridan M, Reddy PV, Morrell A, Cobb BT, Marchand C, Agama K, Chergui A, Renaud A, Stephen AG, Bindu LK, Pommier Y, Cushman M..  (2013)  Synthesis and biological evaluation of indenoisoquinolines that inhibit both tyrosyl-DNA phosphodiesterase I (Tdp1) and topoisomerase I (Top1).,  56  (1): [PMID:23259865] [10.1021/jm3014458]

2. Conda-Sheridan M, Park EJ, Beck DE, Reddy PV, Nguyen TX, Hu B, Chen L, White JJ, van Breemen RB, Pezzuto JM, Cushman M..  (2013)  Design, synthesis, and biological evaluation of indenoisoquinoline rexinoids with chemopreventive potential.,  56  (6): [PMID:23472886] [10.1021/jm400026k]

3.  (2016)  Synthesis and use of dual tyrosyl-DNA phosphodiesterase I (Tdp1)—topoisomerase I (Top1) inhibitors, 

Source

Source(2):

• Scientific Literature
• BindingDB Database