3-(4,5-dinitronaphthalen-1-ylamino)benzoic acid

ID: ALA4758386

PubChem CID: 162656704

Max Phase: Preclinical

Molecular Formula: C17H11N3O6

Molecular Weight: 353.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cccc(Nc2ccc([N+](=O)[O-])c3c([N+](=O)[O-])cccc23)c1

Standard InChI:  InChI=1S/C17H11N3O6/c21-17(22)10-3-1-4-11(9-10)18-13-7-8-15(20(25)26)16-12(13)5-2-6-14(16)19(23)24/h1-9,18H,(H,21,22)

Standard InChI Key:  DEBLYSMOATYNAJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   10.8025  -11.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8012  -12.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5161  -12.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5143  -11.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2296  -11.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2304  -12.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9457  -12.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6607  -12.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6559  -11.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9400  -11.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5119  -10.1952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7961   -9.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7970   -8.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0822   -8.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3680   -8.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3732   -9.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0885  -10.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0801   -7.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7936   -7.3106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3647   -7.3141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0955  -13.3830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3538  -13.3788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4999  -14.1021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2705  -13.3736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1742  -13.3812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9415  -14.0881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  4 11  1  0
 11 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
 14 18  1  0
  3 21  1  0
  7 22  1  0
 21 23  2  0
 21 24  1  0
 22 25  2  0
 22 26  1  0
M  CHG  4  21   1  22   1  24  -1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4758386

   ---

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: 353.29

Molecular Weight (Monoisotopic): 353.0648

AlogP: 4.10

#Rotatable Bonds: 5

Polar Surface Area: 135.61

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.75

CX Basic pKa: ┄

CX LogP: 3.94

CX LogD: 1.34

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.52

Np Likeness Score: -0.95

References

1. Liu Y,He S,Chen Y,Liu Y,Feng F,Liu W,Guo Q,Zhao L,Sun H.  (2020)  Overview of AKR1C3: Inhibitor Achievements and Disease Insights.,  63  (20.0): [PMID:32463235] [10.1021/acs.jmedchem.9b02138]

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):

• Scientific Literature