4,9-dimethyl-11-(4-methoxycarbonylyphenyl)-10H-indolo[3,2-b]quinoline

ID: ALA1760429

PubChem CID: 54581012

Max Phase: Preclinical

Molecular Formula: C25H20N2O2

Molecular Weight: 380.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(-c2c3cccc(C)c3nc3c2[nH]c2c(C)cccc23)cc1

Standard InChI:  InChI=1S/C25H20N2O2/c1-14-6-4-8-18-20(16-10-12-17(13-11-16)25(28)29-3)24-23(26-21(14)18)19-9-5-7-15(2)22(19)27-24/h4-13,27H,1-3H3

Standard InChI Key:  HEDYQMAIMKHNTM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   -4.1726    0.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1737   -0.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4594   -1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4611    0.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7464    0.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463   -0.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9607   -0.9338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4785   -0.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6616   -0.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285    1.1509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1789   -0.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5170   -1.5968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0336   -2.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7878   -2.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235   -1.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6381   -0.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8133    1.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3275    0.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4947    0.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8322    1.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3413    2.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4792    1.9925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2758   -2.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962   -2.7621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200   -3.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4573   -1.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9657    2.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
  7  9  1  0
 15 16  1  0
  8  5  1  0
 16 17  2  0
 17 12  1  0
 10 12  1  0
  1  2  2  0
  5  4  2  0
 18 19  1  0
  8  9  2  0
 19 20  1  0
  4  1  1  0
 20 21  2  0
  9 10  1  0
 21 22  1  0
 10 19  2  0
 22 23  2  0
 23 18  1  0
  5  6  1  0
 18 11  2  0
 11  8  1  0
 24 25  1  0
 24 26  2  0
 15 24  1  0
 25 27  1  0
  2  3  1  0
  3 28  1  0
 12 13  2  0
 23 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1760429

   methyl 4-(4,9-dimethyl-10H-indolo[3,2-b]quinolin-11-yl)benzoate

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: 380.45

Molecular Weight (Monoisotopic): 380.1525

AlogP: 5.94

#Rotatable Bonds: 2

Polar Surface Area: 54.98

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.91

CX Basic pKa: 4.53

CX LogP: 6.31

CX LogD: 6.31

Aromatic Rings: 5

Heavy Atoms: 29

QED Weighted: 0.39

Np Likeness Score: -0.30

References

1. Riechert-Krause F, Eick A, Grünert R, Bednarski PJ, Weisz K..  (2011)  In vitro anticancer activity and evaluation of DNA duplex binding affinity of phenyl-substituted indoloquinolines.,  21  (8): [PMID:21414783] [10.1016/j.bmcl.2011.02.088]

Source

Source(1):

• Scientific Literature