(R)-2-((2-Chloro-4-fluorophenyl)Thio)-4-Oxo-N-((S)-1-Phenylethyl)Azetidine-1-Carboxamide

ID: ALA4548023

PubChem CID: 155553948

Max Phase: Preclinical

Molecular Formula: C18H16ClFN2O2S

Molecular Weight: 378.86

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)N1C(=O)C[C@H]1Sc1ccc(F)cc1Cl)c1ccccc1

Standard InChI:  InChI=1S/C18H16ClFN2O2S/c1-11(12-5-3-2-4-6-12)21-18(24)22-16(23)10-17(22)25-15-8-7-13(20)9-14(15)19/h2-9,11,17H,10H2,1H3,(H,21,24)/t11-,17+/m0/s1

Standard InChI Key:  YSFOYDKIPZXDFY-APPDUMDISA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   11.4036   -5.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4036   -6.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2289   -6.5353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2289   -5.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8190   -7.1200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8136   -5.1254    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.5970   -4.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1815   -3.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9695   -2.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1715   -2.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5857   -3.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8007   -4.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9580   -1.9394    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.8136   -7.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5970   -7.9173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6108   -6.9034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1817   -8.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9789   -8.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5623   -8.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3590   -8.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5721   -7.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9825   -7.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1882   -7.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2228   -4.7034    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.9701   -9.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  1  1  0
  2  5  2  0
  4  6  1  1
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 10 13  1  0
  3 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 12 24  1  0
 17 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4548023

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 378.86

Molecular Weight (Monoisotopic): 378.0605

AlogP: 4.60

#Rotatable Bonds: 4

Polar Surface Area: 49.41

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.82

CX Basic pKa: ┄

CX LogP: 4.27

CX LogD: 4.27

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.79

Np Likeness Score: -1.26

References

1. Kuskovsky R, Lloyd D, Arora K, Plotkin BJ, Green JM, Boshoff HI, Barry C, Deschamps J, Konaklieva MI..  (2019)  C4-Phenylthio β-lactams: Effect of the chirality of the β-lactam ring on antimicrobial activity.,  27  (20): [PMID:31474471] [10.1016/j.bmc.2019.115050]

Source

Source(1):

• Scientific Literature