1-(3-Methylbenzoyl)-5-propionylamino-1H-indazole-3-carboxylic Acid ethyl ester

ID: ALA2409571

PubChem CID: 71818832

Max Phase: Preclinical

Molecular Formula: C21H21N3O4

Molecular Weight: 379.42

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H21N3O4/c1-4-18(25)22-15-9-10-17-16(12-15)19(21(27)28-5-2)23-24(17)20(26)14-8-6-7-13(3)11-14/h6-12H,4-5H2,1-3H3,(H,22,25)

Standard InChI Key:  WMTQOTNFTZMUKV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   17.3660  -18.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3648  -19.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0729  -19.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0711  -17.9160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7797  -18.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7799  -19.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5612  -19.4013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0466  -18.7325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5622  -18.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5476  -20.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8325  -20.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2477  -20.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2305  -21.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9298  -21.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6459  -21.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6582  -20.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9583  -20.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9365  -17.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7527  -17.3018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1947  -17.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4945  -16.6535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3719  -20.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0109  -17.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6582  -17.9164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9505  -18.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2427  -17.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9507  -19.1424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5351  -18.3255    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
 16 22  1  0
 20 23  1  0
  1 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2409571

   Ethyl 1-(3-methylbenzoyl)-5-(propanoylamino)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: 379.42

Molecular Weight (Monoisotopic): 379.1532

AlogP: 3.56

#Rotatable Bonds: 5

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: 13.90

CX Basic pKa: ┄

CX LogP: 3.47

CX LogD: 3.47

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -1.73

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