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CHEBI:66689 - megathyrin A

ChEBI IDCHEBI:66689
ChEBI Namemegathyrin A
Stars
DefinitionA cyclic terpene ketone that is ent-7α,20-epoxy-kaur-16-en-15-one substituted with hydroxy groups at positions 1, 7 and 14 (the 1α,7β,14β stereoisomer). Isolated from the leaves of Isodon megathyrsus, it exhibits cytotoxic activity.
Last Modified5 April 2013
DownloadsMolfile
FormulaC20H28O5
Net Charge0
Average Mass348.439
Monoisotopic Mass348.19367
SMILES[H][C@@]12CC[C@H]3C(=C)C(=O)[C@@]1([C@@H]3O)[C@@]1(O)C[C@]3([H])C(C)(C)CC[C@H](O)[C@@]23CO1
InChIInChI=1S/C20H28O5/c1-10-11-4-5-12-18-9-25-19(24,20(12,15(10)22)16(11)23)8-13(18)17(2,3)7-6-14(18)21/h11-14,16,21,23-24H,1,4-9H2,2-3H3/t11-,12-,13+,14-,16+,18-,19+,20-/m0/s1
InChIKeyVPZCKRKZFRCZMX-FINWQXJNSA-N
Species of MetaboliteComponentSourceComments
Isodon megathyrsus (ncbitaxon:662919) leaf (BTO:0000713) PubMed (7528785)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
megathyrin A (CHEBI:66689) has parent hydride ent-kaurene (CHEBI:15415)
megathyrin A (CHEBI:66689) has role antineoplastic agent (CHEBI:35610)
megathyrin A (CHEBI:66689) has role metabolite (CHEBI:25212)
megathyrin A (CHEBI:66689) is a bridged compound (CHEBI:35990)
megathyrin A (CHEBI:66689) is a cyclic terpene ketone (CHEBI:36130)
megathyrin A (CHEBI:66689) is a lactol (CHEBI:38131)
IUPAC Name 
(1α,5β,7β,8α,9β,10α,13α,14R)-1,7,14-trihydroxy-7,20-epoxykaur-16-en-15-one
Synonym  Source
1α,7β,14β-trihydroxy-ent-7α,20-epoxy-kaur-16-en-15-oneChEBI
Registry NumbersSources
Reaxys:8238556Reaxys
Citations