(S)-2-((3,4-Difluorophenyl)Thio)-4-Oxo-N-((R)-1-Phenylethyl)Azetidine-1-Carboxamide

ID: ALA4515421

PubChem CID: 155540010

Max Phase: Preclinical

Molecular Formula: C18H16F2N2O2S

Molecular Weight: 362.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H](NC(=O)N1C(=O)C[C@@H]1Sc1ccc(F)c(F)c1)c1ccccc1

Standard InChI:  InChI=1S/C18H16F2N2O2S/c1-11(12-5-3-2-4-6-12)21-18(24)22-16(23)10-17(22)25-13-7-8-14(19)15(20)9-13/h2-9,11,17H,10H2,1H3,(H,21,24)/t11-,17+/m1/s1

Standard InChI Key:  HQUZRTXXHWRYCN-DIFFPNOSSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   35.1846  -25.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1846  -26.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0059  -26.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0059  -25.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6026  -27.1819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5879  -25.1967    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.3722  -24.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9541  -23.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7431  -23.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9489  -22.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3658  -23.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5798  -24.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7363  -22.0257    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.5879  -27.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3722  -27.9754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.3813  -26.9663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.9542  -28.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7477  -28.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3284  -28.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1212  -28.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3334  -27.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7466  -27.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9559  -27.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3226  -22.4590    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.7436  -29.3428    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
  9 24  1  0
 17 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4515421

   ---

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: 362.40

Molecular Weight (Monoisotopic): 362.0901

AlogP: 4.09

#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: 3.80

CX LogD: 3.80

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -1.27

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