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CHEBI:70809 - pentalenolactone F

ChEBI IDCHEBI:70809
ChEBI Namepentalenolactone F
Stars
DefinitionA tetracyclic sesquiterpene lactone obtained by formal epoxidation of the 4-methylene group of pentalenolactone E.
Last Modified24 August 2016
SubmitterSteve
DownloadsMolfile
FormulaC15H18O5
Net Charge0
Average Mass278.304
Monoisotopic Mass278.11542
SMILES[H][C@@]12COC(=O)[C@]3(CO3)[C@@]13CC(C)(C)C[C@@]3([H])C=C2C(=O)O
InChIInChI=1S/C15H18O5/c1-13(2)4-8-3-9(11(16)17)10-5-19-12(18)15(7-20-15)14(8,10)6-13/h3,8,10H,4-7H2,1-2H3,(H,16,17)/t8-,10+,14-,15-/m1/s1
InChIKeyUUDKOVSZNMZKND-BDAURDKOSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
ChEBI Ontology
Outgoing Relation(s)
pentalenolactone F (CHEBI:70809) has role bacterial metabolite (CHEBI:76969)
pentalenolactone F (CHEBI:70809) is a organic heterotricyclic compound (CHEBI:26979)
pentalenolactone F (CHEBI:70809) is a sesquiterpene lactone (CHEBI:37667)
pentalenolactone F (CHEBI:70809) is a spiro-epoxide (CHEBI:133131)
pentalenolactone F (CHEBI:70809) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
pentalenolactone F (CHEBI:70809) is conjugate acid of pentalenolactone F(1−) (CHEBI:70789)
Incoming Relation(s)
pentalenolactone F(1−) (CHEBI:70789) is conjugate base of pentalenolactone F (CHEBI:70809)
IUPAC Name 
(2R,4a'R,7a'S,9a'R)-6',6'-dimethyl-3'-oxo-1',5',6',7',7a',9a'-hexahydrospiro[oxirane-2,4'-pentaleno[1,6a-c]pyran]-9'-carboxylic acid
Manual XrefsDatabases
CPD-13622MetaCyc
Registry NumbersSources
Reaxys:5382725Reaxys
Citations