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

ID: ALA4568751

PubChem CID: 155560672

Max Phase: Preclinical

Molecular Formula: C18H17FN2O2S

Molecular Weight: 344.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)N1C(=O)C[C@H]1Sc1ccccc1F)c1ccccc1

Standard InChI:  InChI=1S/C18H17FN2O2S/c1-12(13-7-3-2-4-8-13)20-18(23)21-16(22)11-17(21)24-15-10-6-5-9-14(15)19/h2-10,12,17H,11H2,1H3,(H,20,23)/t12-,17+/m0/s1

Standard InChI Key:  KMQFJQNAKXNSSS-YVEFUNNKSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   34.0413  -22.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0413  -22.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8627  -22.9226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8627  -22.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4594  -23.5046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4446  -21.5193    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.2381  -21.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4460  -22.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2386  -22.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8215  -22.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6064  -21.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8141  -21.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5953  -20.3615    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   35.4446  -23.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2331  -24.2980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.2381  -23.2931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4397  -24.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2240  -25.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4315  -25.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2199  -26.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8022  -26.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5990  -26.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8070  -25.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8577  -23.9276    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
 12 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
 17 24  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4568751

   ---

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: 344.41

Molecular Weight (Monoisotopic): 344.0995

AlogP: 3.95

#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: ┄

CX Basic pKa: ┄

CX LogP: 3.66

CX LogD: 3.66

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.85

Np Likeness Score: -1.08

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