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CHEBI:65651 - colossolactone VIII

ChEBI IDCHEBI:65651
ChEBI Namecolossolactone VIII
Stars
DefinitionA tetracyclic triterpenoid that is A,B-dihomo-19-nor-4-oxalanosta-1,8,19,24-tetraen-26,22-olide substituted by an acetoxy group at position 15, a hydroxy group at position 23 and an oxo group at position 3 (the 22S, 23R stereoisomer). It is isolated from the fruiting bodies of the Vietnamese mushroom Ganoderma colossum and displays inhibitory activity towards the enzyme HIV protease.
Last Modified13 December 2012
DownloadsMolfile
FormulaC32H42O7
Net Charge0
Average Mass538.681
Monoisotopic Mass538.29305
SMILES[H][C@@]1([C@@H](C)[C@@]2([H])C[C@@H](OC(C)=O)[C@@]3(C)C4=C(C=C5C=CC(=O)OC(C)(C)[C@]5([H])CC4)CC[C@]23C)OC(=O)C(C)=C[C@H]1O
InChIInChI=1S/C32H42O7/c1-17-14-25(34)28(38-29(17)36)18(2)24-16-26(37-19(3)33)32(7)23-10-9-22-20(8-11-27(35)39-30(22,4)5)15-21(23)12-13-31(24,32)6/h8,11,14-15,18,22,24-26,28,34H,9-10,12-13,16H2,1-7H3/t18-,22+,24+,25+,26+,28-,31+,32+/m0/s1
InChIKeyXNFBOJFRJTXMJL-OZXCYFAESA-N
Species of MetaboliteComponentSourceComments
Ganoderma colossum (ncbitaxon:36070) - PubMed (18547117)
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.
HIV protease inhibitor  An inhibitor of HIV protease, an enzyme required for production of proteins needed for viral assembly.
ChEBI Ontology
Outgoing Relation(s)
colossolactone VIII (CHEBI:65651) has parent hydride lanostane (CHEBI:20265)
colossolactone VIII (CHEBI:65651) has role HIV protease inhibitor (CHEBI:35660)
colossolactone VIII (CHEBI:65651) has role metabolite (CHEBI:25212)
colossolactone VIII (CHEBI:65651) is a acetate ester (CHEBI:47622)
colossolactone VIII (CHEBI:65651) is a secondary alcohol (CHEBI:35681)
colossolactone VIII (CHEBI:65651) is a tetracyclic triterpenoid (CHEBI:26893)
colossolactone VIII (CHEBI:65651) is a δ-lactone (CHEBI:18946)
colossolactone VIII (CHEBI:65651) is a ε-lactone (CHEBI:50239)
IUPAC Name 
(1R,3R,3aR,11aR,13bR)-3-{(1S)-1-[(2S,3R)-3-hydroxy-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl}-3a,11,11,13b-tetramethyl-9-oxo-1,2,3,3a,4,5,9,11,11a,12,13,13b-dodecahydroindeno[5',4':4,5]cyclohepta[1,2-c]oxepin-1-yl acetate
Synonym  Source
(22S, 23R)-A,B-dihomo-19-nor-15-β-acetoxy-23-hydroxy-4-oxa-3-oxolanosta-1,8,19,24-tetraen-26,22-olideChEBI
Registry NumbersSources
Reaxys:18836345Reaxys
Citations