3-(2,3-Dimethoxy-5,12-dioxo-5,12-dihydro-8,10-dioxa-6-aza-benzo[a]cyclopenta[h]fluoren-6-yl)-propyl-ammonium chloride

ID: ALA421238

Chembl Id: CHEMBL421238

PubChem CID: 9846329

Max Phase: Preclinical

Molecular Formula: C22H21ClN2O6

Molecular Weight: 408.41

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H20N2O6.ClH/c1-27-15-6-11-14(9-16(15)28-2)22(26)24(5-3-4-23)20-12-7-17-18(30-10-29-17)8-13(12)21(25)19(11)20;/h6-9H,3-5,10,23H2,1-2H3;1H

Standard InChI Key:  VSYDJLWBQBQQAK-UHFFFAOYSA-N

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: 408.41

Molecular Weight (Monoisotopic): 408.1321

AlogP: 2.31

#Rotatable Bonds: 5

Polar Surface Area: 102.01

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.57

CX LogP: 0.69

CX LogD: -1.43

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.54

Np Likeness Score: 0.41

References

1. Morrell A, Antony S, Kohlhagen G, Pommier Y, Cushman M..  (2004)  Synthesis of nitrated indenoisoquinolines as topoisomerase I inhibitors.,  14  (14): [PMID:15203138] [10.1016/j.bmcl.2004.05.022]

2. Cushman M, Jayaraman M, Vroman JA, Fukunaga AK, Fox BM, Kohlhagen G, Strumberg D, Pommier Y..  (2000)  Synthesis of new indeno[1,2-c]isoquinolines: cytotoxic non-camptothecin topoisomerase I inhibitors.,  43  (20): [PMID:11020283] [10.1021/jm000029d]

3. Nagarajan M, Morrell A, Fort BC, Meckley MR, Antony S, Kohlhagen G, Pommier Y, Cushman M..  (2004)  Synthesis and anticancer activity of simplified indenoisoquinoline topoisomerase I inhibitors lacking substituents on the aromatic rings.,  47  (23): [PMID:15509164] [10.1021/jm040025z]

4. Morrell A, Jayaraman M, Nagarajan M, Fox BM, Meckley MR, Ioanoviciu A, Pommier Y, Antony S, Hollingshead M, Cushman M..  (2006)  Evaluation of indenoisoquinoline topoisomerase I inhibitors using a hollow fiber assay.,  16  (16): [PMID:16750365] [10.1016/j.bmcl.2006.05.048]

5. 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