CHEBI:66572 - leucosesterterpenone

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ChEBI Name leucosesterterpenone
ChEBI ID CHEBI:66572
Definition A sesterterpenoid isolated from Leucosceptrum canum. It has been shown to exhibit anti-angiogenic and inhibitory activity against prolyl endopeptidase ( EC 3.4.21.26 ).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C25H36O7
Net Charge 0
Average Mass 448.54910
Monoisotopic Mass 448.24610
InChI InChI=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
InChIKey WREVESBXGFRQJD-PHRJMFLCSA-N
SMILES [H][C@]12CC[C@@H](C)[C@]1([H])[C@@](O)(C(=O)[C@@H](C)C[C@H]1[C@H](O)C=C(C)C1=O)[C@]1(O)C=C(C)CO[C@]1(O)[C@@H]2C
Metabolite of Species Details
Leucosceptrum canum (NCBI:txid694369) Found in aerial part (BTO:0001658). See: PubMed
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.
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(s): angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 α-hydroxy ketone (CHEBI:139592)
leucosesterterpenone (CHEBI:66572) is a tertiary alcohol (CHEBI:26878)
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 Number Type Source
9970763 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15524427 PubMed citation Europe PMC
18330714 PubMed citation Europe PMC
Last Modified
07 February 2018