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

ID: ALA4536342

PubChem CID: 155548793

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+/m1/s1

Standard InChI Key:  NHIBOTVVFUWMDN-ACJLOTCBSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.6213  -27.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6213  -28.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4384  -28.4985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4384  -27.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0434  -29.0763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0163  -27.0993    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8048  -26.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3825  -25.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1715  -24.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3814  -24.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8025  -25.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0164  -26.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0163  -29.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8048  -29.8657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8056  -28.8607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3826  -30.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1720  -30.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7485  -30.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5372  -30.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7494  -29.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1667  -29.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3802  -29.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426  -26.6890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6518  -26.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1725  -31.2291    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
 12 23  1  0
 23 24  1  0
 16 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4536342

   ---

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