MetaCyc Compound: penicillin N

Superclasses: a secondary metabolitea xenobiotican antibiotica beta-lactama penama penicillin
an amidea cyclic amidea lactama beta-lactama penama penicillin

Chemical Formula: C14H20N3O6S

Molecular Weight: 358.39 Daltons

Monoisotopic Molecular Weight: 360.1229311444 Daltons

penicillin N compound structure

SMILES: CC2(C)(S[CH]1(N(C(=O)C(NC(=O)CCCC([N+])C(=O)[O-])1)C(C(=O)[O-])2))

InChI: InChI=1S/C14H21N3O6S/c1-14(2)9(13(22)23)17-10(19)8(11(17)24-14)16-7(18)5-3-4-6(15)12(20)21/h6,8-9,11H,3-5,15H2,1-2H3,(H,16,18)(H,20,21)(H,22,23)/p-1/t6-,8-,9+,11-/m1/s1


Unification Links: ChEBI:58408, KEGG:C06564, MetaboLights:MTBLC58408, PubChem:25245855

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 3.2103505Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

deacetylcephalosporin C biosynthesis :
2-oxoglutarate + penicillin N + oxygen → CO2 + succinate + deacetoxycephalosporin C + H2O

Not in pathways:
a β-lactam[periplasm] + H2O[periplasm] → a substituted β-amino acid[periplasm]

Reactions known to both consume and produce the compound:

deacetylcephalosporin C biosynthesis :
isopenicillin N ↔ penicillin N

In Reactions of unknown directionality:

Not in pathways:
a penicillin + H2O = 6-aminopenicillanate + a carboxylate

In Transport reactions:
a xenobiotic[cytosol] + ATP + H2O ↔ a xenobiotic[extracellular space] + ADP + phosphate

Enzymes inhibited by penicillin N, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: deacetoxycephalosporin C hydroxylase [Baker91]

This compound has been characterized as an alternative substrate of the following enzymes: PSE-4 β-lactamase, isopenicillin N epimerase


Baker91: Baker BJ, Dotzlaf JE, Yeh WK (1991). "Deacetoxycephalosporin C hydroxylase of Streptomyces clavuligerus. Purification, characterization, bifunctionality, and evolutionary implication." J Biol Chem 266(8);5087-93. PMID: 2002049

Brakhage98: Brakhage AA (1998). "Molecular regulation of beta-lactam biosynthesis in filamentous fungi." Microbiol Mol Biol Rev 62(3);547-85. PMID: 9729600

Keller05: Keller NP, Turner G, Bennett JW (2005). "Fungal secondary metabolism - from biochemistry to genomics." Nat Rev Microbiol 3(12);937-47. PMID: 16322742

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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