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

ID: ALA4561359

PubChem CID: 155558735

Max Phase: Preclinical

Molecular Formula: C19H20N2O3S

Molecular Weight: 356.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(S[C@H]2CC(=O)N2C(=O)N[C@H](C)c2ccccc2)cc1

Standard InChI:  InChI=1S/C19H20N2O3S/c1-13(14-6-4-3-5-7-14)20-19(23)21-17(22)12-18(21)25-16-10-8-15(24-2)9-11-16/h3-11,13,18H,12H2,1-2H3,(H,20,23)/t13-,18+/m1/s1

Standard InChI Key:  UFACELIHZSALPQ-ACJLOTCBSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   12.4766   -6.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4766   -6.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2979   -6.9296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2979   -6.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8946   -7.5116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8799   -5.5263    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.6642   -4.7328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2461   -4.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0351   -3.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2409   -3.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6578   -3.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8718   -4.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8799   -7.5116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6642   -8.3050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6733   -7.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2462   -8.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0397   -8.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6204   -9.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4132   -9.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6254   -8.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0385   -7.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2479   -7.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0289   -2.3551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6063   -1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0361   -9.6767    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
  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
 10 23  1  0
 23 24  1  0
 16 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4561359

   ---

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: -0.76

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