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

ID: ALA2282127

PubChem CID: 76330789

Max Phase: Preclinical

Molecular Formula: C24H24N2O4

Molecular Weight: 404.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H24N2O4/c1-2-30-24(29)22-18(17-11-7-4-8-12-17)15-19-21(23(28)26(19)22)25-20(27)14-13-16-9-5-3-6-10-16/h3-14,18-19,21-22H,2,15H2,1H3,(H,25,27)/b14-13+

Standard InChI Key:  HDXGAYBGCZWOMV-BUHFOSPRSA-N

Molfile:  

     RDKit          2D

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   11.6418  -27.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4668  -27.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4713  -27.8587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2574  -28.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7387  -27.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2500  -26.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5612  -27.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9770  -28.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8012  -28.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2106  -27.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7897  -26.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9668  -26.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5187  -28.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9701  -29.5089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3266  -29.0606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1453  -29.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7476  -30.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0583  -28.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0604  -26.4488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0351  -25.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7367  -25.1899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3083  -25.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2831  -24.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5564  -24.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5360  -23.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8101  -22.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1076  -23.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1355  -24.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8619  -24.4535    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 29  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2282127

   ethyl 7-oxo-3-phenyl-6-[[(E)-3-phenylprop-2-enoyl]amino]-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: 404.47

Molecular Weight (Monoisotopic): 404.1736

AlogP: 2.51

#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: 12.81

CX Basic pKa: ┄

CX LogP: 2.87

CX LogD: 2.87

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: 0.19

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