Penam

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
CAS Number	53908-04-6 [ChemSpider];
3D model (JSmol)	Interactive image;
Beilstein Reference	4374479
ChEBI	CHEBI:35991 ;
ChemSpider	7827765;
PubChem CID	9548842;
	InChI 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;
	SMILES C1CSC2N1C(=O)C2;
Properties
Chemical formula	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

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.

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