Penam

Penams are the primary skeleton structures that define the penicillin subclass of the broader β-lactam family of antibiotics and related compounds. They are bicyclic ring systems containing a β-lactam moiety fused with a five-member thiazolidine ring. Due to ring strain and limitations on amide resonance, the structure is unstable and highly susceptible to catalytic cleavage at the amide bond. Benzylpenicillin (penicillin G) is the natural product parent that contains the penam structure.

Penam
Names
IUPAC name
(5R)-4-thia-1-azabicyclo[3.2.0]heptan-7-one
Other names
1-Aza-7-oxo-4-thiabicyclo[3.2.0]heptane
Identifiers
3D model (JSmol)
4374479
ChEBI
ChemSpider
  • InChI=1S/C5H7NOS/c7-4-3-5-6(4)1-2-8-5/h5H,1-3H2/t5-/m1/s1
    Key: WSHJJCPTKWSMRR-RXMQYKEDSA-N
  • InChI=1S/C5H7NOS/c7-4-3-5-6(4)1-2-8-5/h5H,1-3H2/t5-/m1/s1
    Key: WSHJJCPTKWSMRR-RXMQYKEDSA-N
  • C1CSC2N1C(=O)C2
Properties
C5H7NOS
Molar mass 129.18 g·mol−1
Related compounds
Related compounds
clavam
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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