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

ID: ALA4521922

PubChem CID: 155542786

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)cc1Cl)c1ccccc1

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

Standard InChI Key:  YSFOYDKIPZXDFY-PIGZYNQJSA-N

Molfile:  

 
     RDKit          2D

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    3.7897   -5.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7897   -6.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6148   -6.2360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6148   -5.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2051   -6.8207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1994   -4.8262    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9828   -4.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5673   -3.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3554   -2.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5576   -2.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9718   -3.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867   -3.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3440   -1.6406    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.1994   -6.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9828   -7.6179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9966   -6.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5675   -8.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3647   -7.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9481   -8.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7445   -8.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9576   -7.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3681   -6.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5739   -7.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6088   -4.4044    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3559   -8.9916    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
  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
 12 24  1  0
 17 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4521922

   ---

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: 13.82

CX Basic pKa: ┄

CX LogP: 4.27

CX LogD: 4.27

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.79

Np Likeness Score: -1.26

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