2,3,6,7-Tetrahydro-1H,5H-3a,4b,8,10-tetraaza-dicyclopenta[a,h]-s-indacene-4,9-dione

ID: ALA20080

PubChem CID: 374655

Max Phase: Preclinical

Molecular Formula: C14H12N4O2

Molecular Weight: 268.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2nc3n(c2C(=O)c2c1nc1n2CCC1)CCC3

Standard InChI:  InChI=1S/C14H12N4O2/c19-13-9-11(17-5-1-3-7(17)15-9)14(20)12-10(13)16-8-4-2-6-18(8)12/h1-6H2

Standard InChI Key:  DTQQFGXBNSEYAW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 24  0  0  0  0  0  0  0  0999 V2000
    4.6417   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625   -3.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0750   -2.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2542   -2.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -3.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2542   -3.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6167   -2.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -4.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -1.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -3.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6167   -3.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1875   -3.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0
  3  1  2  0
  4  2  2  0
  5  3  1  0
  6  1  1  0
  7  2  1  0
  8  1  1  0
  9  3  1  0
 10  4  1  0
 11  7  2  0
 12  6  2  0
 13  5  2  0
 14  8  2  0
 15  9  1  0
 16 10  1  0
 17 12  1  0
 18 11  1  0
 19 18  1  0
 20 17  1  0
  9 12  1  0
  5  4  1  0
 11 10  1  0
 20 15  1  0
 16 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA20080

   4,9,13,18-Tetrazapentacyclo[10.6.0.03,10.04,8.014,18]octadeca-1(12),3(10),8,13-tetraene-2,11-dione

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: 268.28

Molecular Weight (Monoisotopic): 268.0960

AlogP: 0.75

#Rotatable Bonds: ┄

Polar Surface Area: 69.78

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.39

CX LogP: 0.44

CX LogD: 0.44

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.60

Np Likeness Score: -0.18

References

1. Suleman A, Skibo EB..  (2002)  A comprehensive study of the active site residues of DT-diaphorase: rational design of benzimidazolediones as DT-diaphorase substrates.,  45  (6): [PMID:11881990] [10.1021/jm0104365]

2. Schulz WG, Skibo EB..  (2000)  Inhibitors of topoisomerase II based on the benzodiimidazole and dipyrroloimidazobenzimidazole ring systems: controlling DT-diaphorase reductive inactivation with steric bulk.,  43  (4): [PMID:10691689] [10.1021/jm990210q]

3. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays