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

ID: ALA4476070

PubChem CID: 155537753

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)cc1F)c1ccccc1

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

Standard InChI Key:  OKCBIQMGUWDPNS-PIGZYNQJSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   35.8408  -15.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8408  -16.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6621  -16.0260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6621  -15.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2588  -16.6080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2441  -14.6227    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.0285  -13.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6103  -13.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3993  -12.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6051  -12.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0220  -12.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2360  -13.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3926  -11.4517    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   35.6608  -14.2069    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   37.2441  -16.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0285  -17.4014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.0376  -16.3923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6104  -17.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4039  -17.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9846  -18.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7774  -18.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9896  -17.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4028  -16.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6122  -16.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3989  -18.7728    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
 10 13  1  0
 12 14  1  0
  3 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 18 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4476070

   ---

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: 13.82

CX Basic pKa: ┄

CX LogP: 3.80

CX LogD: 3.80

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -1.20

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