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

ID: ALA2312893

PubChem CID: 71546985

Max Phase: Preclinical

Molecular Formula: C23H24ClN3O4

Molecular Weight: 405.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CNc1ccc2c3c(n(CCCN)c(=O)c2c1)-c1ccccc1C3=O.Cl

Standard InChI:  InChI=1S/C23H23N3O4.ClH/c1-2-30-19(27)13-25-14-8-9-15-18(12-14)23(29)26(11-5-10-24)21-16-6-3-4-7-17(16)22(28)20(15)21;/h3-4,6-9,12,25H,2,5,10-11,13,24H2,1H3;1H

Standard InChI Key:  OLKSZMPHPUVHEQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   12.9034  -21.9238    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.9274  -23.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9262  -24.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6368  -24.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6350  -23.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3461  -23.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3496  -24.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0646  -24.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7807  -24.4388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0577  -23.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7778  -23.6119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2314  -22.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0587  -22.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3965  -23.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2209  -23.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7082  -22.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3654  -21.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5420  -21.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0668  -25.6767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4920  -24.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6832  -21.7717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2109  -24.8537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4973  -24.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7821  -24.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0685  -24.4368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3532  -24.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6396  -24.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804  -25.6756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2065  -24.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9209  -24.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6353  -24.4373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  6 10  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
 10 11  2  0
 11 14  1  0
 13 12  1  0
 12 10  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  8 19  2  0
  9 20  1  0
 12 21  2  0
  3 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 24 28  2  0
 20 29  1  0
 29 30  1  0
 30 31  1  0
M  END

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: 405.45

Molecular Weight (Monoisotopic): 405.1689

AlogP: 2.54

#Rotatable Bonds: 7

Polar Surface Area: 103.42

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.57

CX LogP: 0.83

CX LogD: -1.28

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: -0.35

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]

Source

Source(1):

• Scientific Literature