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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 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."

Report Errors or Provide Feedback
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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