2-methoxy-1,3-dinitroanthracene-9,10-dione

ID: ALA2332990

PubChem CID: 71720652

Max Phase: Preclinical

Molecular Formula: C15H8N2O7

Molecular Weight: 328.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c([N+](=O)[O-])cc2c(c1[N+](=O)[O-])C(=O)c1ccccc1C2=O

Standard InChI:  InChI=1S/C15H8N2O7/c1-24-15-10(16(20)21)6-9-11(12(15)17(22)23)14(19)8-5-3-2-4-7(8)13(9)18/h2-6H,1H3

Standard InChI Key:  WNJOXEVUSWPWTO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   27.8037  -22.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8026  -22.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5106  -23.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5088  -21.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2175  -22.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2163  -22.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9225  -23.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9248  -21.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6355  -22.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6339  -22.9043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3395  -23.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0472  -22.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0449  -22.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3387  -21.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9248  -20.8565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9219  -24.1322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7553  -23.3127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7561  -24.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3387  -24.1297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0457  -24.5411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6303  -24.5398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7532  -21.6718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7507  -20.8546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4622  -22.0782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  8 15  2  0
  7 16  2  0
 12 17  1  0
 17 18  1  0
 11 19  1  0
 19 20  2  0
 19 21  1  0
 22 23  2  0
 22 24  1  0
 13 22  1  0
M  CHG  4  19   1  21  -1  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2332990

   2-Methoxy-1,3-dinitroanthracene-9,10-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: 328.24

Molecular Weight (Monoisotopic): 328.0332

AlogP: 2.29

#Rotatable Bonds: 3

Polar Surface Area: 129.65

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.64

CX LogD: 2.64

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.53

Np Likeness Score: -0.11

References

1. Castro-Castillo V, Suárez-Rozas C, Castro-Loiza N, Theoduloz C, Cassels BK..  (2013)  Annulation of substituted anthracene-9,10-diones yields promising selectively antiproliferative compounds.,  62  [PMID:23454511] [10.1016/j.ejmech.2013.01.049]

Source

Source(1):

• Scientific Literature