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ChEBI
> Main
CHEBI:66597 - lupulin A
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ChEBI Ontology
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ChEBI Name
lupulin A
ChEBI ID
CHEBI:66597
Definition
A diterpenoid isolated from
Ajuga lupulina
and has been shown to exhibit anti-inflammatory and antibacterial activities.
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-HKDNVZQMSA-N
SMILES
[H]
[C@]
1(CC2C[C@H]
(OC)
OC2O1)
[C@@]
1(C)
[C@H]
(C)
C[C@H]
(OC(C)
=O)
[C@]
2(COC(C)
=O)
[C@]
1([H]
)
C[C@@H]
(O)
[C@H]
(OC(=O)
C(C)
CC)
[C@]
21CO1
Metabolite of Species
Details
Ajuga lupulina
(NCBI:txid587657)
See:
PubMed
Roles Classification
Biological Role
(s):
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
cyclooxygenase 1 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
Application
(s):
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
lupulin A (
CHEBI:66597
)
has role
anti-inflammatory agent (
CHEBI:67079
)
lupulin A (
CHEBI:66597
)
has role
antibacterial agent (
CHEBI:33282
)
lupulin A (
CHEBI:66597
)
has role
cyclooxygenase 1 inhibitor (
CHEBI:50630
)
lupulin A (
CHEBI:66597
)
has role
cyclooxygenase 2 inhibitor (
CHEBI:50629
)
lupulin A (
CHEBI:66597
)
has role
metabolite (
CHEBI:25212
)
lupulin A (
CHEBI:66597
)
is a
acetate ester (
CHEBI:47622
)
lupulin A (
CHEBI:66597
)
is a
diterpenoid (
CHEBI:23849
)
lupulin A (
CHEBI:66597
)
is a
epoxide (
CHEBI:32955
)
lupulin A (
CHEBI:66597
)
is a
furofuran (
CHEBI:47790
)
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
,5
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
8528547
Reaxys Registry Number
Reaxys
Citations
Types
Sources
17191906
PubMed citation
Europe PMC
19946570
PubMed citation
Europe PMC
21073945
PubMed citation
Europe PMC
8759163
PubMed citation
Europe PMC
Last Modified
25 March 2013