CHEBI:68381 - arjunolic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name arjunolic acid
ChEBI ID CHEBI:68381
Definition A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 23 (the 2α,3β stereoisomer). Isolated from Symplocos lancifolia and Juglans sinensis, it exhibits antioxidant and antimicrobial activities.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB9463336, eMolecules:30512482, eMolecules:2726153, ZINC000003881958
Download Molfile XML SDF
Formula C30H48O5
Net Charge 0
Average Mass 488.69910
Monoisotopic Mass 488.35017
InChI InChI=1S/C30H48O5/c1-25(2)11-13-30(24(34)35)14-12-28(5)18(19(30)15-25)7-8-22-26(3)16-20(32)23(33)27(4,17-31)21(26)9-10-29(22,28)6/h7,19-23,31-33H,8-17H2,1-6H3,(H,34,35)/t19-,20+,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1
InChIKey RWNHLTKFBKYDOJ-DDHMHSPCSA-N
SMILES [H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@]3([H])CC[C@@]12C)C(O)=O
Metabolite of Species Details
Combretum quadrangulare (IPNI:170410-1) Found in leaf (BTO:0000713). Methanolic extract of leaves See: PubMed
Symplocos lancifolia (NCBI:txid239704) Found in leaf (BTO:0000713). Dried, powdered leaves extracted with boiling 80% methanol See: PubMed
Juglans sinensis (NCBI:txid442437-1) Found in twig (BTO:0001411). 80% Methanolic extract of dried leaves and twigs See: PubMed
Juglans sinensis (NCBI:txid442437-1) Found in leaf (BTO:0000713). 80% Methanolic extract of dried leaves and twigs See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing arjunolic acid (CHEBI:68381) has parent hydride oleanane (CHEBI:36481)
arjunolic acid (CHEBI:68381) has role antibacterial agent (CHEBI:33282)
arjunolic acid (CHEBI:68381) has role antifungal agent (CHEBI:35718)
arjunolic acid (CHEBI:68381) has role antioxidant (CHEBI:22586)
arjunolic acid (CHEBI:68381) has role metabolite (CHEBI:25212)
arjunolic acid (CHEBI:68381) is a hydroxy monocarboxylic acid (CHEBI:35868)
arjunolic acid (CHEBI:68381) is a pentacyclic triterpenoid (CHEBI:25872)
Incoming 2α,3β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopynoside (CHEBI:67948) has functional parent arjunolic acid (CHEBI:68381)
3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]arjunolic acid (CHEBI:68378) has functional parent arjunolic acid (CHEBI:68381)
IUPAC Name
(2α,3β)-2,3,23-trihydroxyolean-12-en-28-oic acid
Synonym Source
(2α,3β,4α)-2,3,23-trihydroxyolean-12-en-28-oic acid ChEBI
Manual Xrefs Databases
CN101416970 Patent
GB923414 Patent
HMDB0034502 HMDB
WO2013064326 Patent
View more database links
Registry Numbers Types Sources
2712723 Reaxys Registry Number Reaxys
465-00-9 CAS Registry Number ChemIDplus
Citations Types Sources
21046976 PubMed citation Europe PMC
21732908 PubMed citation Europe PMC
22486656 PubMed citation Europe PMC
23402784 PubMed citation Europe PMC
Last Modified
20 January 2014