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

ID: ALA4474252

PubChem CID: 155536859

Max Phase: Preclinical

Molecular Formula: C19H20N2O3S

Molecular Weight: 356.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccccc1S[C@@H]1CC(=O)N1C(=O)N[C@@H](C)c1ccccc1

Standard InChI:  InChI=1S/C19H20N2O3S/c1-13(14-8-4-3-5-9-14)20-19(23)21-17(22)12-18(21)25-16-11-7-6-10-15(16)24-2/h3-11,13,18H,12H2,1-2H3,(H,20,23)/t13-,18+/m0/s1

Standard InChI Key:  NHIBOTVVFUWMDN-SCLBCKFNSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   20.9250  -27.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9250  -28.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7422  -28.4655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7422  -27.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3472  -29.0433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3200  -27.0663    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.1085  -26.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6862  -25.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4753  -24.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6852  -24.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1062  -25.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3202  -26.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3200  -29.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1085  -29.8327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1094  -28.8277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6864  -30.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4757  -30.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0523  -30.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8410  -30.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0532  -29.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4705  -29.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6840  -29.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7464  -26.6560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9556  -26.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4763  -31.1961    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
  3 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 12 23  1  0
 23 24  1  0
 16 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4474252

   ---

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: 356.45

Molecular Weight (Monoisotopic): 356.1195

AlogP: 3.82

#Rotatable Bonds: 5

Polar Surface Area: 58.64

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.36

CX LogD: 3.36

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -0.73

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