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CHEBI:66055 - hyperinol B

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:
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 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