4-(4-(hexyloxycarbonyl)phenylamino)-3,5-dinitrobenzoic acid

ID: ALA1911376

Cas Number: 299965-41-6

PubChem CID: 3089369

Max Phase: Preclinical

Molecular Formula: C20H21N3O8

Molecular Weight: 431.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCOC(=O)c1ccc(Nc2c([N+](=O)[O-])cc(C(=O)O)cc2[N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C20H21N3O8/c1-2-3-4-5-10-31-20(26)13-6-8-15(9-7-13)21-18-16(22(27)28)11-14(19(24)25)12-17(18)23(29)30/h6-9,11-12,21H,2-5,10H2,1H3,(H,24,25)

Standard InChI Key:  IEYJQEQLVBVCAQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.6582    1.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6594    0.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9453    0.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2296    0.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2324    1.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9470    1.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5180    1.7747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5211    2.5983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972    1.3677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3721    1.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3723    2.5904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0857    1.3571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9435   -0.7107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2298   -1.1206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6573   -1.1202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5152    0.1193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125   -0.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5276   -1.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1249   -2.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6956   -2.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1118   -1.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7026   -0.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1059   -2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6886   -3.4433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9295   -2.7355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990   -4.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6816   -4.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0920   -5.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6747   -6.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0851   -7.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6677   -7.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4 16  1  0
  7  8  2  0
 16 17  1  0
  7  9  1  0
 17 18  2  0
  5  7  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
  1 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  2  0
 22 17  1  0
 10 11  1  0
 20 23  1  0
  5  6  2  0
 23 24  1  0
 10 12  2  0
 23 25  2  0
  6  1  1  0
 24 26  1  0
  1  2  2  0
 26 27  1  0
  3  4  2  0
 27 28  1  0
 13 14  2  0
 28 29  1  0
 13 15  1  0
 29 30  1  0
  3 13  1  0
 30 31  1  0
M  CHG  4   7   1   9  -1  13   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1911376

   4-(4-Hexoxycarbonylanilino)-3,5-dinitrobenzoic acid

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: 431.40

Molecular Weight (Monoisotopic): 431.1329

AlogP: 4.68

#Rotatable Bonds: 11

Polar Surface Area: 161.91

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.53

CX Basic pKa: ┄

CX LogP: 6.47

CX LogD: 3.10

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.22

Np Likeness Score: -0.57

References

1. Corradi V, Mancini M, Santucci MA, Carlomagno T, Sanfelice D, Mori M, Vignaroli G, Falchi F, Manetti F, Radi M, Botta M..  (2011)  Computational techniques are valuable tools for the discovery of protein-protein interaction inhibitors: the 14-3-3σ case.,  21  (22): [PMID:21962576] [10.1016/j.bmcl.2011.09.011]

Source

Source(1):

• Scientific Literature