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CHEBI:65798 - 3,21-dioxoolean-18-en-28-oic acid

ChEBI IDCHEBI:65798
ChEBI Name3,21-dioxoolean-18-en-28-oic acid
Stars
DefinitionA pentacyclic triterpenoid that is olean-18-ene substituted by a carboxy group at position 28 and oxo groups at positions 3 and 21 respectively. Isolated from the leaves of Acacia aulacocarpa, it exhibits inhibitory activity against Tie2 kinase (EC 2.7.10.1) as well as modest activity against a variety of cultured mammalian cells.
Last Modified30 December 2013
DownloadsMolfile
FormulaC30H44O4
Net Charge0
Average Mass468.678
Monoisotopic Mass468.32396
SMILES[H][C@]12CC[C@]3([H])C4=CC(C)(C)C(=O)C[C@]4(C(=O)O)CC[C@@]3(C)[C@]1(C)CC[C@@]1([H])C(C)(C)C(=O)CC[C@]21C
InChIInChI=1S/C30H44O4/c1-25(2)16-19-18-8-9-21-27(5)12-11-22(31)26(3,4)20(27)10-13-29(21,7)28(18,6)14-15-30(19,24(33)34)17-23(25)32/h16,18,20-21H,8-15,17H2,1-7H3,(H,33,34)/t18-,20+,21-,27+,28-,29-,30-/m1/s1
InChIKeyRKRGWMZAXCZBPG-AECKPYPVSA-N
Species of MetaboliteComponentSourceComments
Acacia aulacocarpa (ncbitaxon:138511) leaf (BTO:0000713) PubMed (11735581)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor  An EC 2.7.10.* (protein-tyrosine kinase) inhibitor that interferes with the action of receptor protein-tyrosine kinase (EC 2.7.10.1).
ChEBI Ontology
Outgoing Relation(s)
3,21-dioxoolean-18-en-28-oic acid (CHEBI:65798) has parent hydride oleanane (CHEBI:36481)
3,21-dioxoolean-18-en-28-oic acid (CHEBI:65798) has role EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor (CHEBI:62434)
3,21-dioxoolean-18-en-28-oic acid (CHEBI:65798) has role metabolite (CHEBI:25212)
3,21-dioxoolean-18-en-28-oic acid (CHEBI:65798) is a dioxo monocarboxylic acid (CHEBI:35951)
3,21-dioxoolean-18-en-28-oic acid (CHEBI:65798) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name 
3,21-dioxoolean-18-en-28-oic acid
Registry NumbersSources
Reaxys:9026662Reaxys
Citations