EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:69363 - 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid

ChEBI IDCHEBI:69363
ChEBI Name16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid
Stars
DefinitionA pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 16, 23 and 29 and an oxo group at position 3. It has been isolated from the stem bark of Kalopanax pictus and has been shown to exhibit anti-inflammatory activity.
Last Modified9 January 2014
DownloadsMolfile
FormulaC30H46O6
Net Charge0
Average Mass502.692
Monoisotopic Mass502.32944
SMILES[H][C@]12CC=C3[C@]4([H])C[C@](C)(CO)CC[C@]4(C(=O)O)[C@H](O)C[C@@]3(C)[C@]1(C)CC[C@]1([H])[C@]2(C)CCC(=O)[C@@]1(C)CO
InChIInChI=1S/C30H46O6/c1-25(16-31)12-13-30(24(35)36)19(14-25)18-6-7-21-26(2)10-9-22(33)27(3,17-32)20(26)8-11-28(21,4)29(18,5)15-23(30)34/h6,19-21,23,31-32,34H,7-17H2,1-5H3,(H,35,36)/t19-,20+,21+,23+,25+,26-,27-,28+,29+,30+/m0/s1
InChIKeyXRUBFYYNZLBFBN-JYGFFPNFSA-N
Species of MetaboliteComponentSourceComments
Kalopanax pictus (ncbitaxon:46399) stem (BTO:0001300) PubMed (21870831) Previous component: stem bark; Hot MeOH extract of dried stem bark
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (CHEBI:69363) has parent hydride oleanane (CHEBI:36481)
16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (CHEBI:69363) has role anti-inflammatory agent (CHEBI:67079)
16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (CHEBI:69363) has role plant metabolite (CHEBI:76924)
16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (CHEBI:69363) is a cyclic terpene ketone (CHEBI:36130)
16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (CHEBI:69363) is a hydroxy monocarboxylic acid (CHEBI:35868)
16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (CHEBI:69363) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name 
(16α)-16,23,29-trihydroxy-3-oxoolean-12-en-28-oic acid
Registry NumbersSources
Reaxys:21902579Reaxys
Citations