EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:66572 - leucosesterterpenone

Default Structure
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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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).
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