(3-Benzoylamino-3-benzyl-2-oxo-azetidin-1-yl)-acetic acid methyl ester

ID: ALA175648

PubChem CID: 10383359

Max Phase: Preclinical

Molecular Formula: C20H20N2O4

Molecular Weight: 352.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CN1CC(Cc2ccccc2)(NC(=O)c2ccccc2)C1=O

Standard InChI:  InChI=1S/C20H20N2O4/c1-26-17(23)13-22-14-20(19(22)25,12-15-8-4-2-5-9-15)21-18(24)16-10-6-3-7-11-16/h2-11H,12-14H2,1H3,(H,21,24)

Standard InChI Key:  WHGNQUSSYQLWBX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    6.2750   -5.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8750   -5.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2750   -5.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -4.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8750   -5.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917   -6.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7500   -4.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500   -6.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667   -3.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3042   -4.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5625   -6.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -5.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5667   -7.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8167   -4.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3042   -5.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125   -4.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -5.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4125   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3417   -4.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8292   -5.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -5.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125   -6.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -5.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3417   -5.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  1  1  0
  4  1  1  0
  5  1  1  0
  6  4  1  0
  7  2  1  0
  8  1  1  0
  9  7  1  0
 10  3  2  0
 11  6  2  0
 12  6  1  0
 13  9  2  0
 14  8  1  0
 15  9  1  0
 16 12  1  0
 17 12  2  0
 18 14  2  0
 19 14  1  0
 20 15  1  0
 21 16  2  0
 22 17  1  0
 23 18  1  0
 24 19  2  0
 25 24  1  0
 26 22  2  0
  3  2  1  0
 23 25  2  0
 21 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA175648

   Methyl 2-(3-benzamido-3-benzyl-2-oxoazetidin-1-yl)acetate

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: 352.39

Molecular Weight (Monoisotopic): 352.1423

AlogP: 1.41

#Rotatable Bonds: 6

Polar Surface Area: 75.71

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.92

CX LogD: 1.92

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: -0.50

References

1. Zhijun Wu, Georg GI, Cathers BE, Schloss JV.  (1996)  Synthesis and evaluation of a -lactam-containing dipeptide analog as a protease inhibitor,  6  (8): [10.1016/0960-894X(96)00153-9]

2. Crocetti, Letizia and 8 more authors.  2013-08-08  Optimization of N-benzoylindazole derivatives as inhibitors of human neutrophil elastase.  [PMID:23844670]

Source

Source(1):

• Scientific Literature