US9271961, BMT 5-119

ID: ALA3899044

Cas Number: 39189-41-8

PubChem CID: 45117711

Max Phase: Preclinical

Molecular Formula: C14H9F3N2O4

Molecular Weight: 326.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccccc1Nc1cc(C(F)(F)F)ccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C14H9F3N2O4/c15-14(16,17)8-5-6-12(19(22)23)11(7-8)18-10-4-2-1-3-9(10)13(20)21/h1-7,18H,(H,20,21)

Standard InChI Key:  FZAWUOZTOMHTKK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    2.6024   -2.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6387   -0.8963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004   -2.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9021   -3.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9072   -5.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108   -5.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092   -5.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -6.0070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0195   -7.2070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288   -5.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1992   -2.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1958   -1.7856    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2403   -3.5823    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2366   -2.3825    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 13 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
M  CHG  2  17   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3899044

   2-{[2-Nitro-5-(trifluoromethyl)phenyl]amino}benzoic 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: 326.23

Molecular Weight (Monoisotopic): 326.0514

AlogP: 4.06

#Rotatable Bonds: 4

Polar Surface Area: 92.47

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.74

CX Basic pKa: ┄

CX LogP: 5.19

CX LogD: 1.90

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.65

Np Likeness Score: -1.44

References

1.  (2016)  Bifunctional AKR1C3 inhibitors/androgen receptor modulators and methods of use thereof, 

2. Endo, Satoshi S and 16 more authors.  2017-10-26  Synthesis of Potent and Selective Inhibitors of Aldo-Keto Reductase 1B10 and Their Efficacy against Proliferation, Metastasis, and Cisplatin Resistance of Lung Cancer Cells.  [PMID:28976752]

Source

Source(1):

• BindingDB Database