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CHEBI:65649 - colossolactone V

Default Structure
ChEBI IDCHEBI:65649
ChEBI Namecolossolactone V
Stars
DefinitionA tricyclic triterpenoid that is 3,4-secolanosta-8,24-diene-3,26-dioic acid 3-methylester substituted by acetoxy groups at positions 19 and 22 and a hydroxy group at position 4. It is isolated from the fruiting bodies of the Vietnamese mushroom Ganoderma colossum and displays inhibitory activity towards the enzyme HIV protease.
Last Modified16 March 2015
DownloadsMolfile
FormulaC35H54O9
Net Charge0
Average Mass618.808
Monoisotopic Mass618.37678
SMILES[H][C@@]1(C(C)(C)O)CCC2=C(CC[C@@]3(C)[C@@]2(C)CC[C@]3([H])[C@H](C)[C@@H](C/C=C(/C)C(=O)O)OC(C)=O)[C@]1(CCC(=O)OC)COC(C)=O
InChIInChI=1S/C35H54O9/c1-21(31(39)40)10-12-28(44-24(4)37)22(2)25-14-17-34(8)26-11-13-29(32(5,6)41)35(20-43-23(3)36,19-16-30(38)42-9)27(26)15-18-33(25,34)7/h10,22,25,28-29,41H,11-20H2,1-9H3,(H,39,40)/b21-10-/t22-,25+,28+,29-,33+,34-,35-/m0/s1
InChIKeyNAIJFFZGPGRMSV-SGTCUYSDSA-N
Species of MetaboliteComponentSourceComments
Ganoderma colossum (ncbitaxon:36070) - PubMed (18547117)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
HIV protease inhibitor  An inhibitor of HIV protease, an enzyme required for production of proteins needed for viral assembly.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
ChEBI Ontology
Outgoing Relation(s)
colossolactone V (CHEBI:65649) has parent hydride lanostane (CHEBI:20265)
colossolactone V (CHEBI:65649) has role fungal metabolite (CHEBI:76946)
colossolactone V (CHEBI:65649) has role HIV protease inhibitor (CHEBI:35660)
colossolactone V (CHEBI:65649) is a acetate ester (CHEBI:47622)
colossolactone V (CHEBI:65649) is a dicarboxylic acid monoester (CHEBI:36244)
colossolactone V (CHEBI:65649) is a methyl ester (CHEBI:25248)
colossolactone V (CHEBI:65649) is a tertiary alcohol (CHEBI:26878)
colossolactone V (CHEBI:65649) is a tricyclic triterpenoid (CHEBI:52340)
IUPAC Name 
(2Z,5R,6S)-5-(acetyloxy)-6-[(3R,3aR,6R,7R,9bR)-6-[(acetyloxy)methyl]-7-(2-hydroxypropan-2-yl)-6-(3-methoxy-3-oxopropyl)-3a,9b-dimethyl-2,3,3a,4,5,6,7,8,9,9b-decahydro-1H-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid
Synonym  Source
(22R)-3,4-seco-19,22-diacetoxy-4-hydroxylanosta-8,24(Z)-dien-3,26-dioic acid 3-methylesterChEBI
Registry NumbersSources
Reaxys:18836351Reaxys
Citations