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> Main
CHEBI:67471 - 14-hydro-15-hydroxyajugapitin
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ChEBI Name
14-hydro-15-hydroxyajugapitin
ChEBI ID
CHEBI:67471
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
C29H44O11
Net Charge
0
Average Mass
568.65310
Monoisotopic Mass
568.28836
InChI
InChI=1S/C29H44O11/c1-
7-
14(2)
25(34)
40-
24-
19(32)
11-
20-
27(6,21-
9-
18-
10-
23(33)
39-
26(18)
38-
21)
15(3)
8-
22(37-
17(5)
31)
28(20,12-
35-
16(4)
30)
29(24)
13-
36-
29/h14-
15,18-
24,26,32-
33H,7-
13H2,1-
6H3/t14?,15-
,18+,19-
,20-
,21+,22+,23?,24+,26-
,27+,28+,29-
/m1/s1
InChIKey
SAENNVULKVVZSO-ZDEAQARGSA-N
SMILES
CCC(C)
C(=O)
O[C@H]
1[C@H]
(O)
C[C@@H]
2[C@@]
(C)
([C@@H]
3C[C@H]
4CC(O)
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, C-15 epimeric mixture 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
14-hydro-15-hydroxyajugapitin (
CHEBI:67471
)
has role
antifeedant (
CHEBI:22583
)
14-hydro-15-hydroxyajugapitin (
CHEBI:67471
)
has role
plant metabolite (
CHEBI:76924
)
14-hydro-15-hydroxyajugapitin (
CHEBI:67471
)
is a
acetate ester (
CHEBI:47622
)
14-hydro-15-hydroxyajugapitin (
CHEBI:67471
)
is a
cyclic acetal (
CHEBI:59770
)
14-hydro-15-hydroxyajugapitin (
CHEBI:67471
)
is a
diterpenoid (
CHEBI:23849
)
14-hydro-15-hydroxyajugapitin (
CHEBI:67471
)
is a
furofuran (
CHEBI:47790
)
14-hydro-15-hydroxyajugapitin (
CHEBI:67471
)
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
,6a
R
)-
5-
hydroxyhexahydrofuro[2,3-
b
]furan-
2-
yl]-
5,6-
dimethyloctahydro-
2
H
-
spiro[naphthalene-
1,2'-
oxiran]-
2-
yl 2-
methylbutanoate
Synonym
Source
14-hydro-2,15-dihydroxy-3β-isobutyryloxyclerodin
ChEBI
Registry Number
Type
Source
6552581
Reaxys Registry Number
Reaxys
Citation
Type
Source
21539300
PubMed citation
Europe PMC
Last Modified
24 August 2016