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

ID: ALA4474977

PubChem CID: 155537674

Max Phase: Preclinical

Molecular Formula: C18H13F5N2O2S

Molecular Weight: 416.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)N1C(=O)C[C@H]1Sc1c(F)c(F)c(F)c(F)c1F)c1ccccc1

Standard InChI:  InChI=1S/C18H13F5N2O2S/c1-8(9-5-3-2-4-6-9)24-18(27)25-10(26)7-11(25)28-17-15(22)13(20)12(19)14(21)16(17)23/h2-6,8,11H,7H2,1H3,(H,24,27)/t8-,11+/m0/s1

Standard InChI Key:  FXWWYLBLFPYVNL-GZMMTYOYSA-N

Molfile:  

 
     RDKit          2D

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    4.3377  -17.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377  -17.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1590  -17.9121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1590  -17.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7557  -18.4941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7410  -16.5089    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5253  -15.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1072  -15.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8962  -14.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1020  -14.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5189  -14.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7329  -15.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8894  -13.3378    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.4757  -13.7712    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.8957  -15.3546    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.1576  -16.0889    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7289  -14.5086    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.7368  -18.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5253  -19.2793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5262  -18.2785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1032  -19.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8925  -19.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4691  -20.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2578  -20.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4700  -19.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8873  -18.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1008  -18.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917  -20.6465    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
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 11 12  2  0
 12  7  1  0
 10 13  1  0
  9 14  1  0
  8 15  1  0
 12 16  1  0
 11 17  1  0
  3 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 21 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4474977

   ---

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: 416.37

Molecular Weight (Monoisotopic): 416.0618

AlogP: 4.50

#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: 12.39

CX Basic pKa: ┄

CX LogP: 4.23

CX LogD: 4.23

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.35

Np Likeness Score: -0.70

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