MetaCyc Compound: 3-exomethylenecephalosporin-C

Superclasses: a secondary metabolite a xenobiotic an antibiotic a beta-lactam a cephem a cephalosporin
an amide a cyclic amide a lactam a beta-lactam a cephem a cephalosporin

Citations: [Dotzlaf89]

Chemical Formula: C14H18N3O6S

Molecular Weight: 356.37 Daltons

Monoisotopic Molecular Weight: 357.0994560481 Daltons

3-exomethylenecephalosporin-C compound structure

SMILES: C=C1(CSC2(C(NC(=O)CCCC([N+])C(=O)[O-])C(=O)N(C(C(=O)[O-])1)2))

InChI: InChI=1S/C14H19N3O6S/c1-6-5-24-12-9(11(19)17(12)10(6)14(22)23)16-8(18)4-2-3-7(15)13(20)21/h7,9-10,12H,1-5,15H2,(H,16,18)(H,20,21)(H,22,23)/p-1/t7-,9-,10?,12?/m1/s1


Unification Links: PubChem:25203702

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -21.041872 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

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

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

Enzymes inhibited by 3-exomethylenecephalosporin-C, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: deacetoxycephalosporin C synthase [Dotzlaf89]

This compound has been characterized as an alternative substrate of the following enzymes: deacetoxycephalosporin C hydroxylase


Dotzlaf89: Dotzlaf JE, Yeh WK (1989). "Purification and properties of deacetoxycephalosporin C synthase from recombinant Escherichia coli and its comparison with the native enzyme purified from Streptomyces clavuligerus." J Biol Chem 264(17);10219-27. PMID: 2656705

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
Page generated by SRI International Pathway Tools version 19.0 on Fri Jul 31, 2015, biocyc14.