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CHEBI:66572 - leucosesterterpenone

ChEBI IDCHEBI:66572
ChEBI Nameleucosesterterpenone
Stars
DefinitionA sesterterpenoid isolated from Leucosceptrum canum. It has been shown to exhibit anti-angiogenic and inhibitory activity against prolyl endopeptidase ( EC 3.4.21.26 ).
Last Modified7 February 2018
DownloadsMolfile
FormulaC25H36O7
Net Charge0
Average Mass448.556
Monoisotopic Mass448.24610
SMILES[H][C@]12[C@H](C)CC[C@]1([H])[C@@H](C)[C@@]1(O)OCC(C)=C[C@@]1(O)[C@]2(O)C(=O)[C@@H](C)C[C@@H]1C(=O)C(C)=C[C@H]1O
InChIInChI=1S/C25H36O7/c1-12-10-23(29)24(30,22(28)15(4)8-18-19(26)9-14(3)21(18)27)20-13(2)6-7-17(20)16(5)25(23,31)32-11-12/h9-10,13,15-20,26,29-31H,6-8,11H2,1-5H3/t13-,15+,16-,17-,18+,19-,20+,23-,24-,25-/m1/s1
InChIKeyWREVESBXGFRQJD-PHRJMFLCSA-N
Species of MetaboliteComponentSourceComments
Leucosceptrum canum (ncbitaxon:694369) aerial part (BTO:0001658) PubMed (15524427)
Roles Classification
Biological Roles:
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor  Any EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of prolyl oligopeptidase (EC 3.4.21.26).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
ChEBI Ontology
Outgoing Relation(s)
leucosesterterpenone (CHEBI:66572) has role angiogenesis inhibitor (CHEBI:48422)
leucosesterterpenone (CHEBI:66572) has role EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (CHEBI:76779)
leucosesterterpenone (CHEBI:66572) has role metabolite (CHEBI:25212)
leucosesterterpenone (CHEBI:66572) is a organic heterotricyclic compound (CHEBI:26979)
leucosesterterpenone (CHEBI:66572) is a secondary alcohol (CHEBI:35681)
leucosesterterpenone (CHEBI:66572) is a sesterterpenoid (CHEBI:26660)
leucosesterterpenone (CHEBI:66572) is a terpene ketone (CHEBI:26872)
leucosesterterpenone (CHEBI:66572) is a tertiary alcohol (CHEBI:26878)
leucosesterterpenone (CHEBI:66572) is a tertiary α-hydroxy ketone (CHEBI:139592)
IUPAC Name 
(4R,5S)-4-hydroxy-2-methyl-5-{(2S)-2-methyl-3-oxo-3-[(4aR,5S,5aS,6R,8aS,9R,9aR)-4a,5,9a-trihydroxy-3,6,9-trimethyl-2,4a,5,5a,6,7,8,8a,9,9a-decahydrocyclopenta[g]chromen-5-yl]propyl}cyclopent-2-en-1-one
Registry NumbersSources
Reaxys:9970763Reaxys
Citations