6-[3-(4-aminopiperidinyl)-1-propyl]-5,6-dihydro-2,3-dimethoxy-8,9-methylenedioxy-5,11-dioxo-11H-indeno[1,2-c]isoquinoline dihydrochloride

ID: ALA3216203

PubChem CID: 16090539

Max Phase: Preclinical

Molecular Formula: C27H31Cl2N3O6

Molecular Weight: 491.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c3c(n(CCCN4CCC(N)CC4)c(=O)c2cc1OC)-c1cc2c(cc1C3=O)OCO2.Cl.Cl

Standard InChI:  InChI=1S/C27H29N3O6.2ClH/c1-33-20-10-16-19(13-21(20)34-2)27(32)30(7-3-6-29-8-4-15(28)5-9-29)25-17-11-22-23(36-14-35-22)12-18(17)26(31)24(16)25;;/h10-13,15H,3-9,14,28H2,1-2H3;2*1H

Standard InChI Key:  MWYRSOGNIJCIDF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 38 41  0  0  0  0  0  0  0  0999 V2000
   11.1982    1.7240    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5415   -3.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7987   -2.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7987   -0.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019   -2.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2842   -0.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5415   -0.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238    1.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2488    1.9832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5575    1.8666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2302   -0.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916   -0.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916    1.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4874   -0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4874    1.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446    1.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446   -0.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9841   -0.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9841    1.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4184    1.6822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2861    0.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4184   -0.6906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2163   -2.1561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2377    3.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1082   -3.0720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5404   -4.5824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011   -5.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1402   -2.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5314    4.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5203    5.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8139    6.5068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8050    8.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0995    8.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4031    8.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4121    6.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1176    5.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4387    8.6286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6982    1.7240    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  4  7  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  6 12  1  0
 11 12  1  0
  9 13  1  0
 12 13  2  0
 11 14  1  0
 13 15  1  0
 14 15  2  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 16 19  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 21 22  1  0
 11 23  2  0
  9 24  1  0
  3 25  1  0
  2 26  1  0
 26 27  1  0
 25 28  1  0
 24 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 31 36  1  0
 35 36  1  0
 34 37  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: 491.54

Molecular Weight (Monoisotopic): 491.2056

AlogP: 2.77

#Rotatable Bonds: 6

Polar Surface Area: 105.25

Molecular Species: BASE

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.08

CX LogP: 0.72

CX LogD: -1.89

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.44

Np Likeness Score: 0.02

References

1. Nagarajan M, Morrell A, Ioanoviciu A, Antony S, Kohlhagen G, Agama K, Hollingshead M, Pommier Y, Cushman M..  (2006)  Synthesis and evaluation of indenoisoquinoline topoisomerase I inhibitors substituted with nitrogen heterocycles.,  49  (21): [PMID:17034134] [10.1021/jm060564z]

Source

Source(1):

• Scientific Literature