CHEBI:66054 - hyperinol A

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ChEBI Name hyperinol A
ChEBI ID CHEBI:66054
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H46O3
Net Charge 0
Average Mass 454.68440
Monoisotopic Mass 454.34470
InChI InChI=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
InChIKey NQOAWWBALMIYHN-DVOQMTHLSA-N
SMILES [H][C@@]12CC[C@]3(C)[C@]([H])(CC[C@]45OC(=O)[C@@]6(CCC(=C)[C@@H](C)[C@@]46[H])CC[C@@]35C)[C@@]1(C)CC[C@H](O)C2(C)C
Metabolite of Species Details
Hypericum oblongifolium (NCBI:txid673930) Found in whole plant (BTO:0001461). See: PubMed
Roles Classification
Biological Role(s): 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).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 γ-lactone (CHEBI:37581)
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)
IUPAC Name
(3β,19α)-3-hydroxy-13,28-epoxyurs-20(30)-en-28-one
Synonym Source
3β-hydroxy-20(30)-taraxastene-28,13β-olide ChEBI
Registry Number Type Source
10503874 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
16880649 PubMed citation Europe PMC
Last Modified
27 February 2013