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

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ChEBI Name 3,21-dioxoolean-18-en-28-oic acid
ChEBI ID CHEBI:65798
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H44O4
Net Charge 0
Average Mass 468.66800
Monoisotopic Mass 468.32396
InChI InChI=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
InChIKey RKRGWMZAXCZBPG-AECKPYPVSA-N
SMILES [H][C@]12CC[C@]3([H])[C@@]4(C)CCC(=O)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC[C@]1(CC(=O)C(C)(C)C=C21)C(O)=O
Metabolite of Species Details
Acacia aulacocarpa (NCBI:txid138511) Found in leaf (BTO:0000713). See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
9026662 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
11735581 PubMed citation Europe PMC
Last Modified
30 December 2013