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

ID: ALA4577655

PubChem CID: 155564909

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-SJCJKPOMSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   40.9379  -22.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9379  -23.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7593  -23.1413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.7593  -22.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3560  -23.7233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.3412  -21.7381    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   43.1347  -21.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3426  -22.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1352  -22.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7181  -22.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5030  -21.5807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7107  -21.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4919  -20.5802    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   42.3412  -23.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1297  -24.5168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.1347  -23.5118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.3363  -24.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1206  -25.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3281  -25.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1165  -26.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6988  -27.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4956  -26.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7036  -26.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7543  -24.1463    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  6
  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:

   

   ALA4577655

   ---

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