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ChEBI
> Main
CHEBI:70809 - pentalenolactone F
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ChEBI Ontology
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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.
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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 (Br
o
nsted 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
(2
R
,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
View more database links
Registry Number
Type
Source
5382725
Reaxys Registry Number
Reaxys
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