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ChEBI
> Main
CHEBI:70816 - pentalenolactone
Main
ChEBI Ontology
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ChEBI Name
pentalenolactone
ChEBI ID
CHEBI:70816
Definition
A sesquiterpene lactone that is isolated from several
Streptomyces
species and exhibits antibiotic activity.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C15H16O5
Net Charge
0
Average Mass
276.28450
Monoisotopic Mass
276.09977
InChI
InChI=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
InChIKey
NUPNVWUYFVEAIT-UJJBCWTCSA-N
SMILES
[H][C@@]12COC(=O)[C@]3(CO3)[C@@]11C=C(C)[C@@H](C)[C@@]1([H])C=C2C(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):
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
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
α,β-unsaturated monocarboxylic acid (
CHEBI:79020
)
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 conjugate acid of
pentalenolactone(1−) (
CHEBI:70790
)
Incoming
pentalenolactone(1−) (
CHEBI:70790
)
is conjugate base of
pentalenolactone (
CHEBI:70816
)
IUPAC Name
(2
R
,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
Sources
arenaemycin E
MetaCyc
Arenemycine
ChemIDplus
PA-132
ChemIDplus
Manual Xref
Database
CPD-13619
MetaCyc
View more database links
Registry Numbers
Types
Sources
31501-48-1
CAS Registry Number
ChemIDplus
39567
Reaxys Registry Number
Reaxys
Citations
Types
Sources
11137857
PubMed citation
Europe PMC
11440152
PubMed citation
Europe PMC
13425447
PubMed citation
Europe PMC
13425448
PubMed citation
Europe PMC
16681390
PubMed citation
Europe PMC
16704250
PubMed citation
Europe PMC
16898819
PubMed citation
Europe PMC
17017767
PubMed citation
Europe PMC
17178094
PubMed citation
Europe PMC
19485417
PubMed citation
Europe PMC
21081950
PubMed citation
Europe PMC
21250661
PubMed citation
Europe PMC
21284395
PubMed citation
Europe PMC
2930199
PubMed citation
Europe PMC
3736593
PubMed citation
Europe PMC
3877019
PubMed citation
Europe PMC
3957790
PubMed citation
Europe PMC
5500064
PubMed citation
Europe PMC
6833143
PubMed citation
Europe PMC
7034785
PubMed citation
Europe PMC
8204587
PubMed citation
Europe PMC
8599535
PubMed citation
Europe PMC
Last Modified
24 August 2016