CHEBI:66682 - maslinic acid

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ChEBI Name maslinic acid
ChEBI ID CHEBI:66682
Definition A pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 2 and 3 and a carboxy group at position 28 (the 2α,3β stereoisomer). It is isolated from Olea europaea and Salvia canariensis and exhibits anti-inflammatory, antioxidant and antineoplastic activity.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C30H48O4
Net Charge 0
Average Mass 472.69970
InChI InChI=1S/C30H48O4/c1-25(2)12-14-30(24(33)34)15-13-28(6)18(19(30)16-25)8-9-22-27(5)17-20(31)23(32)26(3,4)21(27)10-11-29(22,28)7/h8,19-23,31-32H,9-17H2,1-7H3,(H,33,34)/t19-,20+,21-,22+,23-,27-,28+,29+,30-/m0/s1
InChIKey MDZKJHQSJHYOHJ-LLICELPBSA-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)(C)[C@]3([H])CC[C@@]12C)C(O)=O
Metabolite of Species Details
Rubia yunnanensis (IPNI:765385-1) Found in root (BTO:0001188). Methanolic extract of air dried powdered roots. See: PubMed
Euptelea polyandra (NCBI:13523) Found in bark (BTO:0001301). See: DOI
Eucalyptus viminalis (NCBI:155764) See: DOI
Symplocos lancifolia (NCBI:239704) Found in leaf (BTO:0000713). Dried, powdered leaves extracted with boiling 80% methanol See: PubMed
Geum japonicum (NCBI:321607) Found in whole plant (BTO:0001461). See: DOI
Olea europaea (NCBI:4146) Found in fruit (BTO:0000486). See: PubMed
Juglans sinensis (NCBI:442437-1) Found in twig (BTO:0001411). 80% Methanolic extract of dried leaves and twigs See: PubMed
Juglans sinensis (NCBI:442437-1) Found in leaf (BTO:0000713). 80% Methanolic extract of dried leaves and twigs See: PubMed
Salvia canariensis (NCBI:49210) Found in aerial part (BTO:0001658). See: PubMed
Luehea divaricata (NCBI:577011) Found in leaf (BTO:0000713). See: J BRAZ CHEM SOC, 2003, 14, 475
Rosa laevigata (NCBI:74652) Found in leaf (BTO:0000713). 70% EtOH extract of dried leaves See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.
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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing maslinic acid (CHEBI:66682) has parent hydride oleanane (CHEBI:36481)
maslinic acid (CHEBI:66682) has role anti-inflammatory agent (CHEBI:67079)
maslinic acid (CHEBI:66682) has role antineoplastic agent (CHEBI:35610)
maslinic acid (CHEBI:66682) has role antioxidant (CHEBI:22586)
maslinic acid (CHEBI:66682) has role metabolite (CHEBI:25212)
maslinic acid (CHEBI:66682) is a dihydroxy monocarboxylic acid (CHEBI:35972)
maslinic acid (CHEBI:66682) is a pentacyclic triterpenoid (CHEBI:25872)
Incoming 2-O-caffeoyl maslinic acid (CHEBI:65547) has functional parent maslinic acid (CHEBI:66682)
3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]maslinic acid (CHEBI:68377) has functional parent maslinic acid (CHEBI:66682)
IUPAC Name
(2α,3β)-2,3-dihydroxyolean-12-en-28-oic acid
Synonyms Sources
Crategolic acid ChemIDplus
Masilinic acid KEGG COMPOUND
Database Links Databases
C16939 KEGG COMPOUND
CN102106861 Patent
CN102579456 Patent
HMDB02392 HMDB
Maslinic_acid Wikipedia
US2011105611 Patent
WO2011015692 Patent
View more database links
Registry Numbers Types Sources
2711878 Reaxys Registry Number Reaxys
4373-41-5 CAS Registry Number KEGG COMPOUND
4373-41-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12802735 PubMed citation CiteXplore
21288041 PubMed citation CiteXplore
21309591 PubMed citation CiteXplore
21384845 PubMed citation CiteXplore
21973054 PubMed citation CiteXplore
23003682 PubMed citation CiteXplore
23175023 PubMed citation CiteXplore
Last Modified
28 July 2014
General Comment
2012-07-27 J BRAZ CHEM SOC, 2003, 14, 475