6-(3-Chloro-propyl)-3-nitro-6a,12a-dihydro-6H-8,10-dioxa-6-aza-benzo[a]cyclopenta[h]fluorene-5,12-dione

ID: ALA123944

Chembl Id: CHEMBL123944

PubChem CID: 44346852

Max Phase: Preclinical

Molecular Formula: C20H15ClN2O6

Molecular Weight: 414.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2cc3c(cc2[C@@H]2[C@H]1c1ccc([N+](=O)[O-])cc1C(=O)N2CCCCl)OCO3

Standard InChI:  InChI=1S/C20H15ClN2O6/c21-4-1-5-22-18-12-7-15-16(29-9-28-15)8-13(12)19(24)17(18)11-3-2-10(23(26)27)6-14(11)20(22)25/h2-3,6-8,17-18H,1,4-5,9H2/t17-,18-/m1/s1

Standard InChI Key:  KOLCHVKMORPDSP-QZTJIDSGSA-N

Alternative Forms

1. Parent:

   

   ALA123944

   cis--6-(3-Chloropropyl)-5,12,13-tetrahydro-2,3-dimethoxy-9,10-methylenedioxy-3-nitro-5,11-dioxo-11H-indeno[1,2-c]isoqu inoline

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: 414.80

Molecular Weight (Monoisotopic): 414.0619

AlogP: 3.43

#Rotatable Bonds: 4

Polar Surface Area: 98.98

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.64

CX Basic pKa: ┄

CX LogP: 2.54

CX LogD: 2.54

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: -0.31

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. Xiao X, Miao ZH, Antony S, Pommier Y, Cushman M..  (2005)  Dihydroindenoisoquinolines function as prodrugs of indenoisoquinolines.,  15  (11): [PMID:15911256] [10.1016/j.bmcl.2005.03.101]

Source

Source(1):

• Scientific Literature