5-Acetylamino-1-(3-methylbenzoyl)-1H-indazole-3-carboxylic Acid ethyl ester

ID: ALA2409570

PubChem CID: 71818831

Max Phase: Preclinical

Molecular Formula: C20H19N3O4

Molecular Weight: 365.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1nn(C(=O)c2cccc(C)c2)c2ccc(NC(C)=O)cc12

Standard InChI:  InChI=1S/C20H19N3O4/c1-4-27-20(26)18-16-11-15(21-13(3)24)8-9-17(16)23(22-18)19(25)14-7-5-6-12(2)10-14/h5-11H,4H2,1-3H3,(H,21,24)

Standard InChI Key:  JKEDHQNDVWMJPW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    4.6293  -18.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6282  -19.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3362  -20.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3344  -18.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0431  -18.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0433  -19.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8246  -20.0658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3100  -19.3969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8255  -18.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8110  -20.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0959  -21.2770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5111  -21.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4939  -22.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1932  -22.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9092  -22.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9216  -21.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2217  -20.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1998  -18.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0161  -17.9663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4581  -18.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7579  -17.3179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6353  -20.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2743  -18.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215  -18.5809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139  -18.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061  -18.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141  -19.8069    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  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
 16 22  1  0
 20 23  1  0
  1 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2409570

   Ethyl 5-acetamido-1-(3-methylbenzoyl)indazole-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: 365.39

Molecular Weight (Monoisotopic): 365.1376

AlogP: 3.17

#Rotatable Bonds: 4

Polar Surface Area: 90.29

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.77

CX LogD: 2.77

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.72

Np Likeness Score: -1.61

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