4-(2,4-dinitrophenoxy)benzoic acid

ID: ALA4788492

Cas Number: 3761-31-7

PubChem CID: 1422323

Max Phase: Preclinical

Molecular Formula: C13H8N2O7

Molecular Weight: 304.21

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(Oc2ccc([N+](=O)[O-])cc2[N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C13H8N2O7/c16-13(17)8-1-4-10(5-2-8)22-12-6-3-9(14(18)19)7-11(12)15(20)21/h1-7H,(H,16,17)

Standard InChI Key:  VIXSKCZNSAEUGB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   34.8957  -22.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7688  -17.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7676  -18.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4757  -18.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1853  -18.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1825  -17.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4739  -17.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8937  -18.8291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8882  -17.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.5975  -17.5976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8851  -16.3745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8950  -19.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1866  -20.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1875  -20.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8964  -21.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6058  -20.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6014  -20.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0628  -17.1908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0626  -16.3736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3551  -17.5996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1877  -22.5010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6031  -22.5023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  5  8  1  0
  9 10  1  0
  9 11  2  0
  6  9  1  0
  8 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 18 19  1  0
 18 20  2  0
  2 18  1  0
 15  1  1  0
  1 21  2  0
  1 22  1  0
M  CHG  4   9   1  10  -1  18   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4788492

   4-(2,4-Dinitrophenoxy)benzoic acid

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: 304.21

Molecular Weight (Monoisotopic): 304.0332

AlogP: 2.99

#Rotatable Bonds: 5

Polar Surface Area: 132.81

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.29

CX Basic pKa: ┄

CX LogP: 3.01

CX LogD: 0.04

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.66

Np Likeness Score: -0.94

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