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CHEBI:66622 - neurolenin C

ChEBI IDCHEBI:66622
ChEBI Nameneurolenin C
Stars
DefinitionA germacranolide isolated from Neurolaena lobata and Austroeupatorium inulifolium and has been shown to exhibit antimalarial activity.
Last Modified7 February 2018
DownloadsMolfile
FormulaC20H28O7
Net Charge0
Average Mass380.437
Monoisotopic Mass380.18350
SMILES[H][C@@]12C[C@@H](C)/C=C\C(=O)[C@@](C)(O)[C@H](OC(=O)CC(C)C)[C@@H](O)[C@@]1([H])C(=C)C(=O)O2
InChIInChI=1S/C20H28O7/c1-10(2)8-15(22)27-18-17(23)16-12(4)19(24)26-13(16)9-11(3)6-7-14(21)20(18,5)25/h6-7,10-11,13,16-18,23,25H,4,8-9H2,1-3,5H3/b7-6-/t11-,13+,16-,17-,18+,20+/m0/s1
InChIKeyPBRMNFXOHFGVPZ-HVACLVPVSA-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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
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 C (CHEBI:66622) has functional parent isovaleric acid (CHEBI:28484)
neurolenin C (CHEBI:66622) has role antimalarial (CHEBI:38068)
neurolenin C (CHEBI:66622) has role metabolite (CHEBI:25212)
neurolenin C (CHEBI:66622) is a enone (CHEBI:51689)
neurolenin C (CHEBI:66622) is a fatty acid ester (CHEBI:35748)
neurolenin C (CHEBI:66622) is a germacranolide (CHEBI:73011)
neurolenin C (CHEBI:66622) is a tertiary α-hydroxy ketone (CHEBI:139592)
IUPAC Name 
(3aR,4S,5R,6S,8Z,10R,11aR)-4,6-dihydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-2,3,3a,4,5,6,7,10,11,11a-decahydrocyclodeca[b]furan-5-yl 3-methylbutanoate
Registry NumbersSources
Reaxys:7314386Reaxys
Citations