ID: ALA187863

Max Phase: Preclinical

Molecular Formula: C20H19ClN2O2

Molecular Weight: 318.38

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cl.NCCCCn1c2c(c3ccccc3c1=O)C(=O)c1ccccc1-2

Standard InChI:  InChI=1S/C20H18N2O2.ClH/c21-11-5-6-12-22-18-14-8-2-3-9-15(14)19(23)17(18)13-7-1-4-10-16(13)20(22)24;/h1-4,7-10H,5-6,11-12,21H2;1H

Standard InChI Key:  DPVMCOIVRZSKKX-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: 318.38

Molecular Weight (Monoisotopic): 318.1368

AlogP: 2.95

#Rotatable Bonds: 4

Polar Surface Area: 65.09

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 10.00

CX LogP: 1.90

CX LogD: -0.57

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.59

Np Likeness Score: 0.12

References

1. 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]

2. 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]

3. Morrell A, Placzek MS, Steffen JD, Antony S, Agama K, Pommier Y, Cushman M..  (2007)  Investigation of the lactam side chain length necessary for optimal indenoisoquinoline topoisomerase I inhibition and cytotoxicity in human cancer cell cultures.,  50  (9): [PMID:17402722] [10.1021/jm0613119]

4. Nguyen TX, Morrell A, Conda-Sheridan M, Marchand C, Agama K, Bermingham A, Stephen AG, Chergui A, Naumova A, Fisher R, O'Keefe BR, Pommier Y, Cushman M..  (2012)  Synthesis and biological evaluation of the first dual tyrosyl-DNA phosphodiesterase I (Tdp1)-topoisomerase I (Top1) inhibitors.,  55  (9): [PMID:22536944] [10.1021/jm300335n]

Source

Source(1):

• Scientific Literature