2-methoxy-[1,3]dioxolo[4,5-g]naphtho[1,2-c]cinnoline

ID: ALA5186082

PubChem CID: 9861272

Max Phase: Preclinical

Molecular Formula: C18H12N2O3

Molecular Weight: 304.31

Names and Identifiers

Canonical SMILES:  COc1ccc2c(ccc3c4cc5c(cc4nnc23)OCO5)c1

Standard InChI:  InChI=1S/C18H12N2O3/c1-21-11-3-5-12-10(6-11)2-4-13-14-7-16-17(23-9-22-16)8-15(14)19-20-18(12)13/h2-8H,9H2,1H3

Standard InChI Key:  IMPABAXTBFQROU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 27  0  0  0  0  0  0  0  0999 V2000
   -1.2277    1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9421    0.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9421   -0.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2277   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5132   -0.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5132    0.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013   -0.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9157   -0.0999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9158    0.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2012    1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6303    1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6303    1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9158    2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013    1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3448    0.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0593    1.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594    1.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3449    2.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7266    0.9800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2115    0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7268   -0.3547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739    2.3746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7740    3.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  9 10  2  0
  6 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  9 11  1  0
 14 10  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 15  1  0
 18 12  1  0
 19 20  1  0
  2 19  1  0
 20 21  1  0
  3 21  1  0
  5  7  1  0
  8  9  1  0
  7  8  2  0
 17 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5186082

   2-Methoxy-8,9-methylenedioxydibenzo[c,h]cinnoline

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 304.31

Molecular Weight (Monoisotopic): 304.0848

AlogP: 3.67

#Rotatable Bonds: 1

Polar Surface Area: 53.47

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.95

CX LogP: 2.98

CX LogD: 2.98

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.50

Np Likeness Score: -0.18

References

1. Talukdar A, Kundu B, Sarkar D, Goon S, Mondal MA..  (2022)  Topoisomerase I inhibitors: Challenges, progress and the road ahead.,  236  [PMID:35413618] [10.1016/j.ejmech.2022.114304]

Source

Source(1):

• Scientific Literature