ID: ALA187631

Max Phase: Preclinical

Molecular Formula: C21H19ClN2O6

Molecular Weight: 394.38

Molecule Type: Small molecule

Representations

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

Standard InChI:  InChI=1S/C21H18N2O6.ClH/c1-26-14-5-10-13(8-15(14)27-2)21(25)23(4-3-22)19-11-6-16-17(29-9-28-16)7-12(11)20(24)18(10)19;/h5-8H,3-4,9,22H2,1-2H3;1H

Standard InChI Key:  HGKJLPYOQQNYSU-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

Properties

Molecular Weight: 394.38

Molecular Weight (Monoisotopic): 394.1165

AlogP: 1.92

#Rotatable Bonds: 4

Polar Surface Area: 102.01

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 8.79

CX LogP: 0.63

CX LogD: -0.77

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: 0.42

References

1. Nagarajan M, Xiao X, Antony S, Kohlhagen G, Pommier Y, Cushman M..  (2003)  Design, synthesis, and biological evaluation of indenoisoquinoline topoisomerase I inhibitors featuring polyamine side chains on the lactam nitrogen.,  46  (26): [PMID:14667224] [10.1021/jm030313f]

2. 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]

3. 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]

Source

Source(1):

• Scientific Literature