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CHEBI:66055 - hyperinol B

Default Structure
ChEBI IDCHEBI:66055
ChEBI Namehyperinol B
Stars
DefinitionA hexacyclic triterpenoid that is 13,28-epoxyursan-28-one with a terminal double bond between positions 20(30) and is substituted by hydroxy groups at position 3 and 22 (the 3β,19α,22α stereoisomer). It is a taraxastane-type triterpene isolated from Hypericum oblongifolium and exhibits enzyme inhibitory activity against chymotrypsin.
Last Modified27 February 2013
DownloadsMolfile
FormulaC30H46O4
Net Charge0
Average Mass470.694
Monoisotopic Mass470.33961
SMILES[H][C@]12CC[C@@]34OC(=O)[C@]5(CC[C@@]3(C)[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](O)CC[C@]21C)[C@@H](O)CC(=C)[C@@H](C)[C@@]45[H]
InChIInChI=1S/C30H46O4/c1-17-16-22(32)29-15-14-28(7)27(6)12-8-19-25(3,4)21(31)10-11-26(19,5)20(27)9-13-30(28,34-24(29)33)23(29)18(17)2/h18-23,31-32H,1,8-16H2,2-7H3/t18-,19+,20-,21+,22+,23-,26+,27-,28+,29-,30+/m1/s1
InChIKeyQYROTRGSZYKHDK-WVDNJEOKSA-N
Species of MetaboliteComponentSourceComments
Hypericum oblongifolium (ncbitaxon:673930) whole plant (BTO:0001461) PubMed (16880649)
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
hyperinol B (CHEBI:66055) has parent hydride taraxastane (CHEBI:72618)
hyperinol B (CHEBI:66055) has role EC 3.4.21.1 (chymotrypsin) inhibitor (CHEBI:64943)
hyperinol B (CHEBI:66055) has role metabolite (CHEBI:25212)
hyperinol B (CHEBI:66055) is a bridged compound (CHEBI:35990)
hyperinol B (CHEBI:66055) is a diol (CHEBI:23824)
hyperinol B (CHEBI:66055) is a hexacyclic triterpenoid (CHEBI:70994)
hyperinol B (CHEBI:66055) is a secondary alcohol (CHEBI:35681)
hyperinol B (CHEBI:66055) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3β,19α,22α)-3,22-dihydroxy-13,28-epoxyurs-20(30)-en-28-one
Synonym  Source
3β,22α-dihydroxy-20(30)-taraxastene-28,13beta-olideChEBI
Registry NumbersSources
Reaxys:10504503Reaxys
Citations