US9271961, BMT 4-90

ID: ALA3945188

PubChem CID: 124222779

Max Phase: Preclinical

Molecular Formula: C14H12N2O5

Molecular Weight: 288.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc([N+](=O)[O-])c(Nc2ccccc2C(=O)O)c1

Standard InChI:  InChI=1S/C14H12N2O5/c1-21-9-6-7-13(16(19)20)12(8-9)15-11-5-3-2-4-10(11)14(17)18/h2-8,15H,1H3,(H,17,18)

Standard InChI Key:  WAXURAGLQIGKCE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    2.5956   -2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    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
   -2.5972   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935   -3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2883   -5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847   -6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8863   -5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8915   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1954   -3.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2317   -3.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2017   -1.8153    0.0000 O   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
   -2.5973    1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956    2.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375    0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  7 18  2  0
 18  3  1  0
  6 19  1  0
 19 20  1  0
 19 21  2  0
M  CHG  2  19   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3945188

   ---

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: 288.26

Molecular Weight (Monoisotopic): 288.0746

AlogP: 3.05

#Rotatable Bonds: 5

Polar Surface Area: 101.70

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.73

CX Basic pKa: ┄

CX LogP: 4.15

CX LogD: 0.86

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.65

Np Likeness Score: -1.07

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