CHEBI:70809 - pentalenolactone F

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ChEBI Name pentalenolactone F
ChEBI ID CHEBI:70809
Definition A tetracyclic sesquiterpene lactone obtained by formal epoxidation of the 4-methylene group of pentalenolactone E.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C15H18O5
Net Charge 0
Average Mass 278.30040
Monoisotopic Mass 278.11542
InChI InChI=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
InChIKey UUDKOVSZNMZKND-BDAURDKOSA-N
SMILES [H][C@@]12CC(C)(C)C[C@]11[C@@]([H])(COC(=O)[C@]11CO1)C(=C2)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing pentalenolactone F (CHEBI:70809) has role bacterial metabolite (CHEBI:76969)
pentalenolactone F (CHEBI:70809) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
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 conjugate acid of pentalenolactone F(1−) (CHEBI:70789)
Incoming 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 Xref Database
CPD-13622 MetaCyc
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Registry Number Type Source
5382725 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16681390 PubMed citation Europe PMC
21250661 PubMed citation Europe PMC
21284395 PubMed citation Europe PMC
6469872 PubMed citation Europe PMC
6833133 PubMed citation Europe PMC
Last Modified
24 August 2016