Trifluoroethyl 4-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)benzoate

ID: ALA4524227

PubChem CID: 117599688

Max Phase: Preclinical

Molecular Formula: C15H9F3N4O5

Molecular Weight: 382.25

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(OCC(F)(F)F)c1ccc(Nc2ccc([N+](=O)[O-])c3nonc23)cc1

Standard InChI:  InChI=1S/C15H9F3N4O5/c16-15(17,18)7-26-14(23)8-1-3-9(4-2-8)19-10-5-6-11(22(24)25)13-12(10)20-27-21-13/h1-6,19H,7H2

Standard InChI Key:  JUOQZAPYUDMLSW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   17.6384  -10.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6372  -11.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3453  -11.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3435   -9.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3410   -9.1085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0475   -8.6978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6321   -8.7020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0521  -10.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0523  -11.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8353  -11.4083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3190  -10.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8349  -10.0764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3455  -12.3802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6379  -12.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9341  -12.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2270  -12.7853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2268  -13.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9396  -14.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6438  -13.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5197  -14.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8114  -13.6056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5210  -14.8303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2294  -15.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2307  -16.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9391  -16.4624    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.5237  -16.4647    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.2241  -16.8721    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  9  1  0
  8  4  1  0
  4  1  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  8  2  0
  3 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
M  CHG  2   5   1   6  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4524227

   2,2,2-Trifluoroethyl 4-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]benzoate

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: 382.25

Molecular Weight (Monoisotopic): 382.0525

AlogP: 3.59

#Rotatable Bonds: 5

Polar Surface Area: 120.39

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.66

CX LogD: 3.66

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.40

Np Likeness Score: -1.64

References

1.  (2014)  Potent analogues of the c-myc inhibitor 10074-g5 with improved cell permeability, 

2. Mancini RS, Barden CJ, Weaver DF, Reed MA..  (2021)  Furazans in Medicinal Chemistry.,  64  (4.0): [PMID:33569941] [10.1021/acs.jmedchem.0c01901]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data