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ChEBI
> Main
CHEBI:67472 - 15-
epi
-lupulin B
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ChEBI Name
15-
epi
-lupulin B
ChEBI ID
CHEBI:67472
ChEBI ASCII Name
15-epi-lupulin B
Definition
A diterpenoid isolated from the aerial parts of
Ajuga bracteosa
and has been shown to exhibit antifeedant activity.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C30H46O11
Net Charge
0
Average Mass
582.67960
Monoisotopic Mass
582.30401
InChI
InChI=1S/C30H46O11/c1-
8-
15(2)
26(34)
41-
25-
20(33)
12-
21-
28(6,22-
10-
19-
11-
24(35-
7)
40-
27(19)
39-
22)
16(3)
9-
23(38-
18(5)
32)
29(21,13-
36-
17(4)
31)
30(25)
14-
37-
30/h15-
16,19-
25,27,33H,8-
14H2,1-
7H3/t15?,16-
,19+,20-
,21-
,22+,23+,24+,25+,27-
,28+,29+,30-
/m1/s1
InChIKey
UEZOFWAZJUOMCN-NTWWNSDMSA-N
SMILES
CCC(C)
C(=O)
O[C@H]
1[C@H]
(O)
C[C@@H]
2[C@@]
(C)
([C@@H]
3C[C@H]
4C[C@@H]
(OC)
O[C@H]
4O3)
[C@H]
(C)
C[C@H]
(OC(C)
=O)
[C@@]
2(COC(C)
=O)
[C@@]
11CO1
Metabolite of Species
Details
Ajuga bracteosa
(IPNI:444535-1)
Found in aerial part
(BTO:0001658)
. Crude dichloromethane extract of dried and powdered aerial parts See:
PubMed
Roles Classification
Biological Role
(s):
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application
(s):
antifeedant
A substance that prevents pests from feeding.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
15-
epi
-lupulin B (
CHEBI:67472
)
has role
antifeedant (
CHEBI:22583
)
15-
epi
-lupulin B (
CHEBI:67472
)
has role
plant metabolite (
CHEBI:76924
)
15-
epi
-lupulin B (
CHEBI:67472
)
is a
acetate ester (
CHEBI:47622
)
15-
epi
-lupulin B (
CHEBI:67472
)
is a
cyclic acetal (
CHEBI:59770
)
15-
epi
-lupulin B (
CHEBI:67472
)
is a
diterpenoid (
CHEBI:23849
)
15-
epi
-lupulin B (
CHEBI:67472
)
is a
furofuran (
CHEBI:47790
)
15-
epi
-lupulin B (
CHEBI:67472
)
is a
spiro-epoxide (
CHEBI:133131
)
IUPAC Name
(1
R
,2
S
,3
R
,4a
R
,5
S
,6
R
,8
S
,8a
R
)-
8-
(acetyloxy)-
8a-
[(acetyloxy)methyl]-
3-
hydroxy-
5-
[(2
S
,3a
S
,5
S
,6a
R
)-
5-
methoxyhexahydrofuro[2,3-
b
]furan-
2-
yl]-
5,6-
dimethyloctahydro-
2
H
-
spiro[naphthalene-
1,2'-
oxiran]-
2-
yl 2-
methylbutanoate
Registry Number
Type
Source
10136512
Reaxys Registry Number
Reaxys
Citation
Type
Source
21539300
PubMed citation
Europe PMC
Last Modified
24 August 2016