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> Main
CHEBI:66089 - isosecotanapartholide
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ChEBI Name
isosecotanapartholide
ChEBI ID
CHEBI:66089
Definition
A sesquiterpene lactone isolated from
Artemisia rutifolia
and
Artemisia iwayomogi
and has been shown to inhibit nitric oxide synthase.
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-
7(16)
4-
5-
10-
8(2)
15(19)
20-
14(10)
13-
9(3)
11(17)
6-
12(13)
18/h10-
11,14,17H,2,4-
6H2,1,3H3/t10-
,11-
,14-
/m0/s1
InChIKey
XXYRTFCLQHKIDU-MJVIPROJSA-N
SMILES
CC(=O)CC[C@@H]1[C@H](OC(=O)C1=C)C1=C(C)[C@@H](O)CC1=O
Metabolite of Species
Details
Artemisia rutifolia
(NCBI:txid205374)
See:
DOI
Artemisia iwayomogi
(NCBI:txid265784)
See:
PubMed
Roles Classification
Biological Role
(s):
EC 1.14.13.39 (nitric oxide synthase) inhibitor
An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
isosecotanapartholide (
CHEBI:66089
)
has role
EC 1.14.13.39 (nitric oxide synthase) inhibitor (
CHEBI:61908
)
isosecotanapartholide (
CHEBI:66089
)
has role
metabolite (
CHEBI:25212
)
isosecotanapartholide (
CHEBI:66089
)
is a
butan-4-olide (
CHEBI:22950
)
isosecotanapartholide (
CHEBI:66089
)
is a
enone (
CHEBI:51689
)
isosecotanapartholide (
CHEBI:66089
)
is a
methyl ketone (
CHEBI:51867
)
isosecotanapartholide (
CHEBI:66089
)
is a
secondary alcohol (
CHEBI:35681
)
isosecotanapartholide (
CHEBI:66089
)
is a
sesquiterpene lactone (
CHEBI:37667
)
IUPAC Name
(4
S
,5
S
)-
5-
[(3
S
)-
3-
hydroxy-
2-
methyl-
5-
oxocyclopent-
1-
en-
1-
yl]-
3-
methylidene-
4-
(3-
oxobutyl)dihydrofuran-
2(3
H
)-
one
Registry Number
Type
Source
6521695
Reaxys Registry Number
Reaxys
Citation
Type
Source
12735688
PubMed citation
Europe PMC
Last Modified
04 March 2013