CHEBI:66621 - neurolenin B

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ChEBI Name neurolenin B
ChEBI ID CHEBI:66621
Definition A germacranolide isolated from Neurolaena lobata and Austroeupatorium inulifolium and has been shown to exhibit antimalarial activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB8292656, ChemicalBook:CB5208584, eMolecules:475163, ZINC000008437654
Download Molfile XML SDF
Formula C22H30O8
Net Charge 0
Average Mass 422.46880
Monoisotopic Mass 422.19407
InChI InChI=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
InChIKey UVRIFAYGSSDVER-MBZNIOTRSA-N
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
Metabolite of Species Details
Neurolaena cobanensis (IPNI:234380-1) See: PHARM PHARMACOL LETT,1998,8,119
Austroeupatorium inulifolium (NCBI:txid103744) Found in stem (BTO:0001300). See: PubMed
Austroeupatorium inulifolium (NCBI:txid103744) Found in leaf (BTO:0000713). See: PubMed
Neurolaena lobata (NCBI:txid183056) Found in aerial part (BTO:0001658). See: DOI
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.
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(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
9163718 Reaxys Registry Number Reaxys
Citations Types Sources
10479310 PubMed citation Europe PMC
12116880 PubMed citation Europe PMC
Last Modified
07 February 2018
General Comment
2012-07-27 PHARM PHARMACOL LETT,1998,8,119