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

ID: ALA557541

PubChem CID: 16090529

Max Phase: Preclinical

Molecular Formula: C24H21ClN4O6

Molecular Weight: 460.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c3c(n(CCCn4cncn4)c(=O)c2cc1OC)-c1cc2c(cc1C3=O)OCO2.Cl

Standard InChI:  InChI=1S/C24H20N4O6.ClH/c1-31-17-6-13-16(9-18(17)32-2)24(30)28(5-3-4-27-11-25-10-26-27)22-14-7-19-20(34-12-33-19)8-15(14)23(29)21(13)22;/h6-11H,3-5,12H2,1-2H3;1H

Standard InChI Key:  PSSHRQLUYSNEPT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
    9.8990    1.4883    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
    4.9429    7.9884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4083    8.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1660    7.0146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691    5.8939    0.0000 C   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  2  0
 33 34  1  0
 31 35  1  0
 34 35  2  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: 460.45

Molecular Weight (Monoisotopic): 460.1383

AlogP: 2.64

#Rotatable Bonds: 6

Polar Surface Area: 106.70

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.29

CX LogP: 1.03

CX LogD: 1.03

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.38

Np Likeness Score: -0.27

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