5-(Cyclopropanecarbonylamino)-1-(3-methylbenzoyl)-1H-indazole-3-carboxylic Acid Ethyl Ester

ID: ALA2409575

PubChem CID: 71818964

Max Phase: Preclinical

Molecular Formula: C22H21N3O4

Molecular Weight: 391.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1nn(C(=O)c2cccc(C)c2)c2ccc(NC(=O)C3CC3)cc12

Standard InChI:  InChI=1S/C22H21N3O4/c1-3-29-22(28)19-17-12-16(23-20(26)14-7-8-14)9-10-18(17)25(24-19)21(27)15-6-4-5-13(2)11-15/h4-6,9-12,14H,3,7-8H2,1-2H3,(H,23,26)

Standard InChI Key:  ADRQRUHQDUYTFF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   17.6095   -3.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6083   -4.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3164   -5.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3146   -3.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0232   -3.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0235   -4.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8047   -4.9601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2901   -4.2913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8057   -3.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7911   -5.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0760   -6.1714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4912   -6.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4740   -7.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1734   -7.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8894   -7.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9017   -6.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2018   -5.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1800   -2.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9962   -2.8606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4382   -3.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7380   -2.2123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6154   -5.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2544   -3.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9017   -3.4753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1941   -3.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4862   -3.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1942   -4.7012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0814   -2.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6730   -3.4746    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
 28 26  1  0
 29 28  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2409575

   Ethyl 5-(cyclopropanecarbonylamino)-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: 391.43

Molecular Weight (Monoisotopic): 391.1532

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: 13.73

CX Basic pKa: ┄

CX LogP: 3.55

CX LogD: 3.55

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: -1.79

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