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CHEBI:66610 - nalanthalide
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ChEBI Name
nalanthalide
ChEBI ID
CHEBI:66610
Definition
A pyranone diterpenoid isolated from
Nalanthamala
and
Chaunopycnis alba
and has been shown to be a blocker of the voltage-gated potassium channel Kv1.3
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C30H44O5
Net Charge
0
Average Mass
484.66740
Monoisotopic Mass
484.31887
InChI
InChI=1S/C30H44O5/c1-
18(2)
11-
10-
15-
30(8)
25-
13-
12-
19(3)
24(29(25,7)
16-
14-
26(30)
35-
22(6)
31)
17-
23-
27(32)
20(4)
21(5)
34-
28(23)
33-
9/h11,24-
26H,3,10,12-
17H2,1-
2,4-
9H3/t24-
,25-
,26+,29-
,30+/m1/s1
InChIKey
RVADBFKZGNOVDI-PELMAWFUSA-N
SMILES
[H][C@@]12CCC(=C)[C@@H](Cc3c(OC)oc(C)c(C)c3=O)[C@@]1(C)CC[C@H](OC(C)=O)[C@@]2(C)CCC=C(C)C
Metabolite of Species
Details
Chaunopycnis alba
(NCBI:txid124418)
of strain MF 6799 See:
DOI
Nalanthamala
(NCBI:txid160956)
of strain MF 5638 See:
DOI
Roles Classification
Biological Role
(s):
potassium channel blocker
An agent that inhibits cell membrane glycoproteins that are selectively permeable to potassium ions.
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
nalanthalide (
CHEBI:66610
)
has role
metabolite (
CHEBI:25212
)
nalanthalide (
CHEBI:66610
)
has role
potassium channel blocker (
CHEBI:50509
)
nalanthalide (
CHEBI:66610
)
is a
4-pyranones (
CHEBI:131906
)
nalanthalide (
CHEBI:66610
)
is a
ortho
-fused bicyclic hydrocarbon (
CHEBI:35428
)
nalanthalide (
CHEBI:66610
)
is a
acetate ester (
CHEBI:47622
)
nalanthalide (
CHEBI:66610
)
is a
diterpenoid (
CHEBI:23849
)
nalanthalide (
CHEBI:66610
)
is a
enol ether (
CHEBI:47985
)
nalanthalide (
CHEBI:66610
)
is a
ketene acetal (
CHEBI:145408
)
IUPAC Name
(1
S
,2
S
,4a
R
,5
R
,8a
R
)-
5-
[(2-
methoxy-
5,6-
dimethyl-
4-
oxo-
4
H
-
pyran-
3-
yl)methyl]-
1,4a-
dimethyl-
6-
methylidene-
1-
(4-
methylpent-
3-
en-
1-
yl)decahydronaphthalen-
2-
yl acetate
Synonyms
Sources
(−)-nalanthalide
ChEBI
3-
[[(1
R
,4a
R
,5
S
,6
S
,8a
R
)-
6-
(acetyloxy)decahydro-
5,8a-
dimethyl-
2-
methylene-
5-
(4-
methyl-
3-
pentenyl)-
1-
naphthalenyl]methyl]-
2-
methoxy-
5,6-
dimethyl-
4
H
-
pyran-
4-
one
ChEBI
Registry Number
Type
Source
6162225
Reaxys Registry Number
Reaxys
Last Modified
18 November 2019
General Comment
2013-04-15
Tetrahedron Lett.
(2001), 42, 1255 - 1258.