(S)-2-((3-Chloro-4-fluorophenyl)Thio)-4-Oxo-N-((R)-1-Phenylethyl)Azetidine-1-Carboxamide

ID: ALA4520608

PubChem CID: 155542279

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)c(Cl)c1)c1ccccc1

Standard InChI:  InChI=1S/C18H16ClFN2O2S/c1-11(12-5-3-2-4-6-12)21-18(24)22-16(23)10-17(22)25-13-7-8-15(20)14(19)9-13/h2-9,11,17H,10H2,1H3,(H,21,24)/t11-,17+/m1/s1

Standard InChI Key:  GBOJQLWUINHAMW-DIFFPNOSSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    4.5946  -17.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5946  -18.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4199  -18.2791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4199  -17.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0099  -18.8638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0045  -16.8691    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7879  -16.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3725  -15.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1605  -14.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625  -14.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7766  -15.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917  -15.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1490  -13.6831    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.0045  -18.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7879  -19.6610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8018  -18.6471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3727  -20.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1698  -20.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7533  -20.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5500  -20.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7631  -19.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1735  -19.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3791  -19.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9830  -14.8593    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1610  -21.0350    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
 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
 11 24  1  0
 17 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4520608

   ---

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: 13.81

CX Basic pKa: ┄

CX LogP: 4.27

CX LogD: 4.27

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.79

Np Likeness Score: -1.35

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