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CHEBI:66431 - schisanlactone A

ChEBI IDCHEBI:66431
ChEBI Nameschisanlactone A
Stars
DefinitionA tetracyclic triterpenoid isolated from Schisandra and Kadsura longipedunculata. It has been shown to exhibit inhibitory activity against HIV protease.
Last Modified26 April 2013
DownloadsMolfile
FormulaC30H40O4
Net Charge0
Average Mass464.646
Monoisotopic Mass464.29266
SMILES[H][C@]1([C@@H](C)[C@@]2([H])CC[C@@]3(C)C4=C(C=C5C=CC(=O)OC(C)(C)[C@]5([H])CC4)CC[C@@]32C)CC=C(C)C(=O)O1
InChIInChI=1S/C30H40O4/c1-18-7-11-25(33-27(18)32)19(2)22-14-16-30(6)24-10-9-23-20(8-12-26(31)34-28(23,3)4)17-21(24)13-15-29(22,30)5/h7-8,12,17,19,22-23,25H,9-11,13-16H2,1-6H3/t19-,22+,23+,25+,29+,30-/m0/s1
InChIKeyVJNOAOVMGNCSPJ-ZCTPSQTASA-N
Species of MetaboliteComponentSourceComments
Schisandra (ncbitaxon:13673) - DOI (10.1016/S0040-4039(00)81922-X)
Kadsura longipedunculata (ncbitaxon:124782)
stem (BTO:0001300) PubMed (16394567)
root (BTO:0001188) PubMed (16394567)
Roles Classification
Biological Roles:
HIV protease inhibitor  An inhibitor of HIV protease, an enzyme required for production of proteins needed for viral assembly.
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)
schisanlactone A (CHEBI:66431) has role HIV protease inhibitor (CHEBI:35660)
schisanlactone A (CHEBI:66431) has role metabolite (CHEBI:25212)
schisanlactone A (CHEBI:66431) is a tetracyclic triterpenoid (CHEBI:26893)
schisanlactone A (CHEBI:66431) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(3R,3aR,11aR,13bR)-3a,11,11,13b-tetramethyl-3-{(1S)-1-[(2R)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl}-2,3,3a,4,5,11,11a,12,13,13b-decahydroindeno[5',4':4,5]cyclohepta[1,2-c]oxepin-9(1H)-one
Registry NumbersSources
Reaxys:10310316Reaxys
Citations