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.
Supplier Information
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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
(1S,2S,4aR,5R,8aR)-5-[(2-methoxy-5,6-dimethyl-4-oxo-4H-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-[[(1R,4aR,5S,6S,8aR)-6-(acetyloxy)decahydro-5,8a-dimethyl-2-methylene-5-(4-methyl-3-pentenyl)-1-naphthalenyl]methyl]-2-methoxy-5,6-dimethyl-4H-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.