CHEBI:65651 - colossolactone VIII

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ChEBI Name colossolactone VIII
ChEBI ID CHEBI:65651
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C32H42O7
Net Charge 0
Average Mass 538.67170
Monoisotopic Mass 538.29305
InChI InChI=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
InChIKey XNFBOJFRJTXMJL-OZXCYFAESA-N
SMILES [H][C@]1(OC(=O)C(C)=C[C@H]1O)[C@@H](C)[C@@]1([H])C[C@@H](OC(C)=O)[C@@]2(C)C3=C(CC[C@]12C)C=C1C=CC(=O)OC(C)(C)[C@]1([H])CC3
Metabolite of Species Details
Ganoderma colossum (NCBI:txid36070) See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 δ-lactone (CHEBI:18946)
colossolactone VIII (CHEBI:65651) is a ε-lactone (CHEBI:50239)
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)
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-olide ChEBI
Registry Number Type Source
18836345 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
18547117 PubMed citation Europe PMC
Last Modified
13 December 2012