ethyl 6-benzamido-7-oxo-3-phenyl-1-azabicyclo[3.2.0]heptane-2-carboxylate

ID: ALA2282130

PubChem CID: 76319903

Max Phase: Preclinical

Molecular Formula: C22H22N2O4

Molecular Weight: 378.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1C(c2ccccc2)CC2C(NC(=O)c3ccccc3)C(=O)N21

Standard InChI:  InChI=1S/C22H22N2O4/c1-2-28-22(27)19-16(14-9-5-3-6-10-14)13-17-18(21(26)24(17)19)23-20(25)15-11-7-4-8-12-15/h3-12,16-19H,2,13H2,1H3,(H,23,25)

Standard InChI Key:  OIQHMRNJBRQMSA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   13.2968  -18.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2962  -19.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1211  -18.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1257  -19.0421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9117  -19.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3930  -18.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9044  -17.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2155  -18.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6314  -19.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4556  -19.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8650  -18.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4441  -17.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6213  -17.9040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1731  -20.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6244  -20.6923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9810  -20.2440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7996  -20.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4019  -21.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7126  -19.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7147  -17.6322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6894  -16.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3910  -16.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9626  -16.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9392  -15.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2133  -15.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5108  -15.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5387  -16.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2651  -16.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  4  1  0
  3  1  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  3  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  6  8  1  0
 14 15  1  0
 14 16  2  0
  5 14  1  0
 15 17  1  0
 17 18  1  0
  2 19  2  0
  1 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2282130

   Ethyl 6-benzamido-7-oxo-3-phenyl-1-azabicyclo[3.2.0]heptane-2-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: 378.43

Molecular Weight (Monoisotopic): 378.1580

AlogP: 2.12

#Rotatable Bonds: 5

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: 2.36

CX LogD: 2.36

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.64

Np Likeness Score: -0.12

References

1. Jarrahpour A, Sheikh J, El-Mounsi I, Mouhoub R, Hadda TB.  (2013)  Computational evaluation and experimental verification of antibacterial activity of some -lactams: advantages and limitations,  22  (3): [10.1007/s00044-012-0126-7]

Source

Source(1):

• Scientific Literature