ethyl 2-(3-(1,3-dioxoisoindolin-2-ylamino)-2-(hydroxymethyl)-4-oxoazetidin-1-yl)-3-phenylpropanoate

ID: ALA2282136

PubChem CID: 76312682

Max Phase: Preclinical

Molecular Formula: C23H23N3O6

Molecular Weight: 437.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C(Cc1ccccc1)N1C(=O)C(NN2C(=O)c3ccccc3C2=O)C1CO

Standard InChI:  InChI=1S/C23H23N3O6/c1-2-32-23(31)17(12-14-8-4-3-5-9-14)25-18(13-27)19(22(25)30)24-26-20(28)15-10-6-7-11-16(15)21(26)29/h3-11,17-19,24,27H,2,12-13H2,1H3

Standard InChI Key:  CTOJJXMYOBOMJU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   23.3091   -1.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5564   -0.7593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5253   -1.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5372   -2.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3283   -2.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5921   -3.6619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8275   -3.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1078   -2.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0978   -1.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8056   -1.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8023   -2.2079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6272   -2.1975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2085   -2.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2079   -3.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0329   -3.6082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0329   -2.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6165   -2.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4132   -2.4140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6243   -4.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6162   -4.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4027   -4.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4131   -3.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9964   -4.5614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6266   -3.1812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7934   -4.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3767   -4.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9861   -5.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7708   -6.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3533   -6.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1512   -6.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3633   -5.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7792   -5.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  4  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  3 10  2  0
  1 11  1  0
  5 11  1  0
 11 12  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 13  1  0
 13 12  1  0
 16 17  1  0
 17 18  1  0
 14 19  2  0
 15 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 25 26  1  0
 21 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2282136

   Ethyl 2-[3-[(1,3-dioxoisoindol-2-yl)amino]-2-(hydroxymethyl)-4-oxoazetidin-1-yl]-3-phenylpropanoate

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: 437.45

Molecular Weight (Monoisotopic): 437.1587

AlogP: 0.53

#Rotatable Bonds: 8

Polar Surface Area: 116.25

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.72

CX LogP: 1.35

CX LogD: 1.35

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.35

Np Likeness Score: -0.22

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