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CHEBI:66621 - neurolenin B

ChEBI IDCHEBI:66621
ChEBI Nameneurolenin B
Stars
DefinitionA germacranolide isolated from Neurolaena lobata and Austroeupatorium inulifolium and has been shown to exhibit antimalarial activity.
Last Modified7 February 2018
DownloadsMolfile
FormulaC22H30O8
Net Charge0
Average Mass422.474
Monoisotopic Mass422.19407
SMILES[H][C@@]12C[C@@H](C)/C=C\C(=O)[C@@](C)(O)[C@H](OC(C)=O)[C@@H](OC(=O)CC(C)C)[C@@]1([H])C(=C)C(=O)O2
InChIInChI=1S/C22H30O8/c1-11(2)9-17(25)30-19-18-13(4)21(26)29-15(18)10-12(3)7-8-16(24)22(6,27)20(19)28-14(5)23/h7-8,11-12,15,18-20,27H,4,9-10H2,1-3,5-6H3/b8-7-/t12-,15+,18-,19-,20+,22+/m0/s1
InChIKeyUVRIFAYGSSDVER-MBZNIOTRSA-N
Species of MetaboliteComponentSourceComments
Neurolaena cobanensis (IPNI:234380-1) - Article (PHARM PHARMACOL LETT,1998,8,119)
Austroeupatorium inulifolium (ncbitaxon:103744)
stem (BTO:0001300) PubMed (12116880)
leaf (BTO:0000713) PubMed (12116880)
Neurolaena lobata (ncbitaxon:183056) aerial part (BTO:0001658) DOI (10.1021/jo00416a020)
Roles Classification
Biological Roles:
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
ChEBI Ontology
Outgoing Relation(s)
neurolenin B (CHEBI:66621) has functional parent isovaleric acid (CHEBI:28484)
neurolenin B (CHEBI:66621) has role antimalarial (CHEBI:38068)
neurolenin B (CHEBI:66621) has role metabolite (CHEBI:25212)
neurolenin B (CHEBI:66621) is a acetate ester (CHEBI:47622)
neurolenin B (CHEBI:66621) is a enone (CHEBI:51689)
neurolenin B (CHEBI:66621) is a fatty acid ester (CHEBI:35748)
neurolenin B (CHEBI:66621) is a germacranolide (CHEBI:73011)
neurolenin B (CHEBI:66621) is a tertiary α-hydroxy ketone (CHEBI:139592)
IUPAC Name 
(3aS,4S,5R,6S,8Z,10R,11aR)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-2,3,3a,4,5,6,7,10,11,11a-decahydrocyclodeca[b]furan-4-yl 3-methylbutanoate
Registry NumbersSources
Reaxys:9163718Reaxys
Citations