MetaCyc Compound: 3-exomethylenecephalosporin-C

Superclasses: a secondary metabolitea xenobiotican antibiotica beta-lactama cephema cephalosporin
an amidea cyclic amidea lactama beta-lactama cephema cephalosporin

Citations: [Dotzlaf89 ]

Chemical Formula: C14H18N3O6S

Molecular Weight: 356.37 Daltons

Monoisotopic Molecular Weight: 358.1072810802 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): -21.041872Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

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

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


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

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

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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