4,5-dinitrobenzo[d][1,3]dioxole

ID: ALA206829

PubChem CID: 3723425

Max Phase: Preclinical

Molecular Formula: C7H4N2O6

Molecular Weight: 212.12

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4,5-Dinitrobenzo[D][1,3]Dioxole | CHEMBL206829|4,5-dinitrobenzo[d][1,3]dioxole|Dinitro-methylendioxybenzole|BDBM50182121|AKOS022141662

Canonical SMILES:  O=[N+]([O-])c1ccc2c(c1[N+](=O)[O-])OCO2

Standard InChI:  InChI=1S/C7H4N2O6/c10-8(11)4-1-2-5-7(15-3-14-5)6(4)9(12)13/h1-2H,3H2

Standard InChI Key:  PAHDCKCVXHLYQB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    3.8506    0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495    0.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5639   -0.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5621    1.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2771    0.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2773    0.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0673   -0.2089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5554    0.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0669    1.1351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1358    1.2864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4218    0.8739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1356    2.1109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5581    2.1174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8428    2.5275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2709    2.5318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  4  1  1  0
  5  6  1  0
 10 11  2  0
 10 12  1  0
  1 10  1  0
  2  3  1  0
  3  6  2  0
  1  2  2  0
 13 14  2  0
 13 15  1  0
  4 13  1  0
M  CHG  4  10   1  12  -1  13   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA206829

   4,5-Dinitrobenzo[d][1,3]dioxole

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: 212.12

Molecular Weight (Monoisotopic): 212.0069

AlogP: 1.23

#Rotatable Bonds: 2

Polar Surface Area: 104.74

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.48

CX LogD: 1.48

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.54

Np Likeness Score: -0.45

References

1. Andricopulo AD, Akoachere MB, Krogh R, Nickel C, McLeish MJ, Kenyon GL, Arscott LD, Williams CH, Davioud-Charvet E, Becker K..  (2006)  Specific inhibitors of Plasmodium falciparum thioredoxin reductase as potential antimalarial agents.,  16  (8): [PMID:16458512] [10.1016/j.bmcl.2006.01.027]

Source

Source(1):

• Scientific Literature