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

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ChEBI Name 28,29-dihydroxyfriedelan-3-one
ChEBI ID CHEBI:65788
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H50O3
Net Charge 0
Average Mass 458.71620
Monoisotopic Mass 458.376
InChI InChI=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
InChIKey ZMSNKXDPESNSSS-CUKXIHTOSA-N
SMILES [H][C@@]12CCC(=O)[C@H](C)[C@@]1(C)CC[C@@]1([H])[C@@]2(C)CC[C@@]2(C)[C@]3([H])C[C@](C)(CO)CC[C@]3(CO)CC[C@]12C
Metabolite of Species Details
Maytenus diversifolia (NCBI:txid490239) Found in stem (BTO:0001300). See: PubMed
Roles Classification
Biological Role(s): 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 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-one ChEBI
Manual Xref Database
10270945 ChemSpider
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Registry Number Type Source
5139108 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12713415 PubMed citation Europe PMC
2095372 PubMed citation Europe PMC
Last Modified
25 October 2016