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CHEBI:66054 - hyperinol A

ChEBI IDCHEBI:66054
ChEBI Namehyperinol A
Stars
DefinitionA hexacyclic triterpenoid that is 13,28-epoxyursan-28-one with a terminal double bond between positions 20(30) and is substituted by a hydroxy group at position 3 (the 3β,19α stereoisomer). It is a taraxastane-type triterpene isolated from Hypericum oblongifolium and exhibits enzyme inhibitory activity against chymotrypsin.
Last Modified27 February 2013
DownloadsMolfile
FormulaC30H46O3
Net Charge0
Average Mass454.695
Monoisotopic Mass454.34470
SMILES[H][C@]12CC[C@]34OC(=O)[C@@]5(CCC(=C)[C@@H](C)[C@]53[H])CC[C@@]4(C)[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](O)CC[C@]21C
InChIInChI=1S/C30H46O3/c1-18-8-14-29-17-16-28(7)27(6)13-9-20-25(3,4)22(31)11-12-26(20,5)21(27)10-15-30(28,33-24(29)32)23(29)19(18)2/h19-23,31H,1,8-17H2,2-7H3/t19-,20+,21-,22+,23-,26+,27-,28+,29+,30+/m1/s1
InChIKeyNQOAWWBALMIYHN-DVOQMTHLSA-N
Species of MetaboliteComponentSourceComments
Hypericum oblongifolium (ncbitaxon:673930) whole plant (BTO:0001461) PubMed (16880649)
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 3.4.21.1 (chymotrypsin) inhibitor  An EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of chymotrypsin (EC 3.4.21.1).
ChEBI Ontology
Outgoing Relation(s)
hyperinol A (CHEBI:66054) has parent hydride taraxastane (CHEBI:72618)
hyperinol A (CHEBI:66054) has role EC 3.4.21.1 (chymotrypsin) inhibitor (CHEBI:64943)
hyperinol A (CHEBI:66054) has role metabolite (CHEBI:25212)
hyperinol A (CHEBI:66054) is a bridged compound (CHEBI:35990)
hyperinol A (CHEBI:66054) is a hexacyclic triterpenoid (CHEBI:70994)
hyperinol A (CHEBI:66054) is a secondary alcohol (CHEBI:35681)
hyperinol A (CHEBI:66054) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3β,19α)-3-hydroxy-13,28-epoxyurs-20(30)-en-28-one
Synonym  Source
3β-hydroxy-20(30)-taraxastene-28,13β-olideChEBI
Registry NumbersSources
Reaxys:10503874Reaxys
Citations