1-(3-Methoxybenzoyl)-5-nitro-1H-indazole-3-carboxylic Acid ethyl ester

ID: ALA2409457

PubChem CID: 71818829

Max Phase: Preclinical

Molecular Formula: C18H15N3O6

Molecular Weight: 369.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1nn(C(=O)c2cccc(OC)c2)c2ccc([N+](=O)[O-])cc12

Standard InChI:  InChI=1S/C18H15N3O6/c1-3-27-18(23)16-14-10-12(21(24)25)7-8-15(14)20(19-16)17(22)11-5-4-6-13(9-11)26-2/h4-10H,3H2,1-2H3

Standard InChI Key:  SIYHDAGPPJTNHW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   16.2640  -26.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2628  -27.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9709  -27.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9691  -25.8981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6777  -26.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6780  -27.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4592  -27.3834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9447  -26.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4602  -26.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4456  -28.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7306  -28.5946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1457  -28.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1286  -29.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8279  -29.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5439  -29.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5563  -28.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8563  -28.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8345  -25.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6508  -25.2838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0927  -25.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3926  -24.6355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5555  -25.8987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8479  -26.3075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5553  -25.0815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9090  -25.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2699  -28.2424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9715  -28.6614    0.0000 C   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  1  0
  8  9  2  0
  9  5  1  0
  7 10  1  0
 10 11  2  0
 10 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
  9 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 22 23  2  0
 22 24  1  0
  1 22  1  0
 20 25  1  0
 16 26  1  0
 26 27  1  0
M  CHG  2  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2409457

   Ethyl 1-(3-methoxybenzoyl)-5-nitroindazole-3-carboxylate

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: 369.33

Molecular Weight (Monoisotopic): 369.0961

AlogP: 2.82

#Rotatable Bonds: 5

Polar Surface Area: 113.56

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.80

CX LogD: 2.80

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.39

Np Likeness Score: -1.50

References

1. Crocetti L, Schepetkin IA, Cilibrizzi A, Graziano A, Vergelli C, Giomi D, Khlebnikov AI, Quinn MT, Giovannoni MP..  (2013)  Optimization of N-benzoylindazole derivatives as inhibitors of human neutrophil elastase.,  56  (15): [PMID:23844670] [10.1021/jm400742j]

Source

Source(1):

• Scientific Literature