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CHEBI:70816 - pentalenolactone

ChEBI IDCHEBI:70816
ChEBI Namepentalenolactone
Stars
DefinitionA sesquiterpene lactone that is isolated from several Streptomyces species and exhibits antibiotic activity.
Last Modified24 August 2016
SubmitterSteve
DownloadsMolfile
FormulaC15H16O5
Net Charge0
Average Mass276.288
Monoisotopic Mass276.09977
SMILES[H][C@@]12COC(=O)[C@]3(CO3)[C@@]13C=C(C)[C@@H](C)[C@@]3([H])C=C2C(=O)O
InChIInChI=1S/C15H16O5/c1-7-4-14-10(8(7)2)3-9(12(16)17)11(14)5-19-13(18)15(14)6-20-15/h3-4,8,10-11H,5-6H2,1-2H3,(H,16,17)/t8-,10-,11+,14-,15-/m1/s1
InChIKeyNUPNVWUYFVEAIT-UJJBCWTCSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
EC 1.2.1.12 [glyceraldehyde-3-phosphate dehydrogenase (phosphorylating)] inhibitor  An EC 1.2.1.* (oxidoreductase acting on donor aldehyde/oxo group with NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of glyceraldehyde-3-phosphate dehydrogenase (EC 1.2.1.12).
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
ChEBI Ontology
Outgoing Relation(s)
pentalenolactone (CHEBI:70816) has role antimicrobial agent (CHEBI:33281)
pentalenolactone (CHEBI:70816) has role bacterial metabolite (CHEBI:76969)
pentalenolactone (CHEBI:70816) has role EC 1.2.1.12 [glyceraldehyde-3-phosphate dehydrogenase (phosphorylating)] inhibitor (CHEBI:70817)
pentalenolactone (CHEBI:70816) is a organic heterotricyclic compound (CHEBI:26979)
pentalenolactone (CHEBI:70816) is a sesquiterpene lactone (CHEBI:37667)
pentalenolactone (CHEBI:70816) is a spiro-epoxide (CHEBI:133131)
pentalenolactone (CHEBI:70816) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
pentalenolactone (CHEBI:70816) is conjugate acid of pentalenolactone(1−) (CHEBI:70790)
Incoming Relation(s)
pentalenolactone(1−) (CHEBI:70790) is conjugate base of pentalenolactone (CHEBI:70816)
IUPAC Name 
(2R,4a'S,7'S,7a'R,9a'R)-6',7'-dimethyl-3'-oxo-1',7',7a',9a'-tetrahydrospiro[oxirane-2,4'-pentaleno[1,6a-c]pyran]-9'-carboxylic acid
Synonyms  Source
arenaemycin EMetaCyc
ArenemycineChemIDplus
PA-132ChemIDplus
Manual XrefsDatabases
CPD-13619MetaCyc
Registry NumbersSources
Reaxys:39567Reaxys
CAS:31501-48-1ChemIDplus
Citations