(5,11-Dioxo-5,11-dihydro-indeno[1,2-c]isoquinolin-6-yl)-acetic acid methyl ester

ID: ALA342160

PubChem CID: 10591700

Max Phase: Preclinical

Molecular Formula: C19H13NO4

Molecular Weight: 319.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)Cn1c2c(c3ccccc3c1=O)C(=O)c1ccccc1-2

Standard InChI:  InChI=1S/C19H13NO4/c1-24-15(21)10-20-17-12-7-3-4-8-13(12)18(22)16(17)11-6-2-5-9-14(11)19(20)23/h2-9H,10H2,1H3

Standard InChI Key:  YZLBGCGHCZWAON-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    1.4167   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -1.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -2.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -0.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -1.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -3.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167   -3.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500    0.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -4.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -4.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042    0.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -5.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208   -1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208   -2.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7250    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  8  1  0
  5  1  1  0
  6  1  1  0
  7  2  1  0
  8  6  1  0
  9  5  1  0
 10  3  1  0
 11 10  1  0
 12  4  2  0
 13  5  2  0
 14 11  2  0
 15  6  2  0
 16  7  1  0
 17 11  1  0
 18  8  2  0
 19  9  1  0
 20 17  1  0
 21 16  2  0
 22 15  1  0
 23 22  2  0
 24 19  2  0
  7  9  2  0
  4  3  1  0
 23 18  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA342160

   5,6-Dihydro-5,11-diketo-6-(methoxycarbonylmethyl)-11H-indeno[1,2-c]isoquinoline

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: 319.32

Molecular Weight (Monoisotopic): 319.0845

AlogP: 2.39

#Rotatable Bonds: 2

Polar Surface Area: 65.37

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.74

CX LogD: 1.74

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.53

Np Likeness Score: -0.19

References

1. Strumberg D, Pommier Y, Paull K, Jayaraman M, Nagafuji P, Cushman M..  (1999)  Synthesis of cytotoxic indenoisoquinoline topoisomerase I poisons.,  42  (3): [PMID:9986716] [10.1021/jm9803323]

Source

Source(1):

• Scientific Literature