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CHEBI:65788 - 28,29-dihydroxyfriedelan-3-one

ChEBI IDCHEBI:65788
ChEBI Name28,29-dihydroxyfriedelan-3-one
Stars
DefinitionA pentacyclic triterpenoid that is friedelane substituted by hydroxy groups at positions 28 and 29 and an oxo group at position 3. Isolated from the stems of Maytenus diversifolia, it exhibits potent cytotoxicity against the A-549 lung carcinoma cells.
Last Modified25 October 2016
DownloadsMolfile
FormulaC30H50O3
Net Charge0
Average Mass458.727
Monoisotopic Mass458.37600
SMILES[H][C@]12CC[C@]3(C)[C@@H](C)C(=O)CC[C@@]3([H])[C@]1(C)CC[C@@]1(C)[C@]3([H])C[C@](C)(CO)CC[C@]3(CO)CC[C@]21C
InChIInChI=1S/C30H50O3/c1-20-21(33)7-8-22-26(20,3)10-9-23-27(22,4)12-13-29(6)24-17-25(2,18-31)11-15-30(24,19-32)16-14-28(23,29)5/h20,22-24,31-32H,7-19H2,1-6H3/t20-,22+,23-,24-,25+,26+,27-,28+,29-,30+/m0/s1
InChIKeyZMSNKXDPESNSSS-CUKXIHTOSA-N
Species of MetaboliteComponentSourceComments
Maytenus diversifolia (ncbitaxon:490239) stem (BTO:0001300) PubMed (2095372)
Roles Classification
Biological Role:
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)
28,29-dihydroxyfriedelan-3-one (CHEBI:65788) has parent hydride friedelane (CHEBI:71575)
28,29-dihydroxyfriedelan-3-one (CHEBI:65788) has role metabolite (CHEBI:25212)
28,29-dihydroxyfriedelan-3-one (CHEBI:65788) is a cyclic terpene ketone (CHEBI:36130)
28,29-dihydroxyfriedelan-3-one (CHEBI:65788) is a diol (CHEBI:23824)
28,29-dihydroxyfriedelan-3-one (CHEBI:65788) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name 
(4R,4aS,6aS,6bR,8aR,11R,12aS,12bS,14aS,14bS)-8a,11-bis(hydroxymethyl)-4,4a,6b,11,12b,14a-hexamethylicosahydropicen-3(2H)-one
Synonym  Source
28,29-dihydroxy-D:A-friedooleanan-3-oneChEBI
Manual XrefsDatabases
10270945ChemSpider
Registry NumbersSources
Reaxys:5139108Reaxys
Citations