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

ID: ALA4553122

PubChem CID: 155556400

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]1Sc1ccc(F)cc1)c1ccccc1

Standard InChI:  InChI=1S/C18H17FN2O2S/c1-12(13-5-3-2-4-6-13)20-18(23)21-16(22)11-17(21)24-15-9-7-14(19)8-10-15/h2-10,12,17H,11H2,1H3,(H,20,23)/t12-,17-/m1/s1

Standard InChI Key:  NSIPFBFYAKEYEQ-SJKOYZFVSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   29.3900   -5.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3900   -6.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2113   -6.0752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2113   -5.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8080   -6.6572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7932   -4.6720    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.7891   -6.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5776   -7.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5785   -6.4416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1563   -7.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9457   -6.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5193   -7.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3080   -7.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5202   -6.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9375   -5.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1510   -6.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5817   -3.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1594   -3.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9485   -2.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1584   -2.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5794   -2.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7934   -3.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9458   -1.5202    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.9448   -7.8088    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
  3  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  6 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 10 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4553122

   ---

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: -1.10

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