4,4'-(2-fluoro-1,4-phenylene)bis(oxy)bis(1,3-dinitrobenzene)

ID: ALA4741254

PubChem CID: 162646495

Max Phase: Preclinical

Molecular Formula: C18H9FN4O10

Molecular Weight: 460.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc(Oc2ccc(Oc3ccc([N+](=O)[O-])cc3[N+](=O)[O-])c(F)c2)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C18H9FN4O10/c19-13-9-12(32-17-4-1-10(20(24)25)7-14(17)22(28)29)3-6-16(13)33-18-5-2-11(21(26)27)8-15(18)23(30)31/h1-9H

Standard InChI Key:  ZYUYUPPPCOYNTH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   17.8777   -6.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8766   -7.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5846   -7.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2943   -7.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2915   -6.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5828   -5.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9976   -5.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9946   -5.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7025   -4.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6997   -3.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9900   -3.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2815   -3.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.1686   -7.5628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4612   -7.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.0528   -7.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7599   -7.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7594   -8.3811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0531   -8.7922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4685   -8.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3441   -5.9238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3436   -5.1066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6366   -6.3328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4153   -5.1047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4157   -5.9219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1228   -4.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9839   -2.6581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6895   -2.2459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2741   -2.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0026   -7.5618    0.0000 F   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
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 18 19  1  0
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 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
  4 33  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:

   

   ALA4741254

   ---

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: 460.29

Molecular Weight (Monoisotopic): 460.0303

AlogP: 5.04

#Rotatable Bonds: 8

Polar Surface Area: 191.02

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.88

CX LogD: 4.88

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.32

Np Likeness Score: -0.95

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