1,4-bis(2,4-dinitrophenoxy)benzene

ID: ALA4762376

Cas Number: 4434-08-6

PubChem CID: 346118

Max Phase: Preclinical

Molecular Formula: C18H10N4O10

Molecular Weight: 442.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc(Oc2ccc(Oc3ccc([N+](=O)[O-])cc3[N+](=O)[O-])cc2)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C18H10N4O10/c23-19(24)11-1-7-17(15(9-11)21(27)28)31-13-3-5-14(6-4-13)32-18-8-2-12(20(25)26)10-16(18)22(29)30/h1-10H

Standard InChI Key:  DARCHGCFBMXFFD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    6.3834   -5.8441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3823   -6.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0903   -7.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8000   -6.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7971   -5.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0885   -5.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5033   -5.4293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5002   -4.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2081   -4.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2054   -3.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4956   -2.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7871   -3.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7933   -4.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6742   -7.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9668   -6.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9720   -5.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2655   -5.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5565   -5.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5584   -6.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2656   -7.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2650   -7.8899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5588   -8.3011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9742   -8.2960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8497   -5.4327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8493   -4.6155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1422   -5.8416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9209   -4.6136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9213   -5.4308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6284   -4.2046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4895   -2.1670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1952   -1.7548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7798   -1.7620    0.0000 O   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
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  2 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 21 22  1  0
 21 23  2  0
 20 21  1  0
 24 25  1  0
 24 26  2  0
 18 24  1  0
 27 28  1  0
 27 29  2  0
  9 27  1  0
 30 31  1  0
 30 32  2  0
 11 30  1  0
M  CHG  8  21   1  22  -1  24   1  25  -1  27   1  28  -1  30   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4762376

   1-[4-(2,4-Dinitrophenoxy)phenoxy]-2,4-dinitrobenzene

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 442.30

Molecular Weight (Monoisotopic): 442.0397

AlogP: 4.90

#Rotatable Bonds: 8

Polar Surface Area: 191.02

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 14

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.73

CX LogD: 4.73

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.34

Np Likeness Score: -0.64

References

1. Makley LN,Johnson OT,Ghanakota P,Rauch JN,Osborn D,Wu TS,Cierpicki T,Carlson HA,Gestwicki JE.  (2021)  Chemical validation of a druggable site on Hsp27/HSPB1 using in silico solvent mapping and biophysical methods.,  34  [PMID:33549906] [10.1016/j.bmc.2020.115990]

Source

Source(1):

• Scientific Literature