Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

MetaCyc Compound: penicillin N

Superclasses: a secondary metabolite a xenobiotic an antibiotic a beta-lactam a penam a penicillin
an amide a cyclic amide a lactam a beta-lactam a penam a penicillin

Chemical Formula: C14H20N3O6S

Molecular Weight: 358.39 Daltons

Monoisotopic Molecular Weight: 359.1151061123 Daltons

SMILES: CC2(C)(SC1(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

InChIKey: InChIKey=MIFYHUACUWQUKT-GPUHXXMPSA-M

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

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 3.2103505 Inferred 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[periplasmic space] + H2O[periplasmic space] → a substituted β-amino acid[periplasmic space]

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]


References

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

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
Page generated by SRI International Pathway Tools version 18.5 on Tue Nov 25, 2014, biocyc14.