CHEBI:37659 - oleanolic acid

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ChEBI Name oleanolic acid
ChEBI ID CHEBI:37659
Definition A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a β-hydroxy group at position 3.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C30H48O3
Net Charge 0
Average Mass 456.70030
Monoisotopic Mass 456.360
InChI InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1
InChIKey MIJYXULNPSFWEK-GTOFXWBISA-N
SMILES [H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O
Metabolite of Species Details
Radermachera boniana (IPNI:110489-1) Found in leaf (BTO:0000713). Ethylacetate extract of dried and ground mixture of twigs and leaves See: PubMed
Radermachera boniana (IPNI:110489-1) Found in twig (BTO:0001411). Ethylacetate extract of dried and ground mixture of twigs and leaves See: PubMed
Symplocos lancifolia (NCBI:239704) Found in leaf (BTO:0000713). Dried, powdered leaves extracted with boiling 80% methanol See: PubMed
Diospyros kaki (NCBI:35925) Found in calyx (BTO:0000169). See: PubMed
Rhododendron (NCBI:4346) See: PubMed
Juglans sinensis (NCBI:442437-1) Found in leaf (BTO:0000713). 80% Methanolic extract of dried leaves and twigs See: PubMed
Juglans sinensis (NCBI:442437-1) Found in twig (BTO:0001411). 80% Methanolic extract of dried leaves and twigs See: PubMed
Panax japonicus var. major (NCBI:45211) Found in root (BTO:0001188). Ethanolic extract of dried and pulverized roots See: PubMed
Paeonia rockii subsp. rockii (NCBI:459179) Found in root (BTO:0001188). Isolated from chloroform soluble extract of air-dried and powdered roots See: PubMed
Rhododendron ferrugineum (NCBI:49622) Found in leaf (BTO:0000713). MeOH extract of CHCl3 soluble fraction of air-dried,powdered leaves,ursolic & oleanolic acid mixture 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): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing oleanolic acid (CHEBI:37659) has parent hydride oleanane (CHEBI:36481)
oleanolic acid (CHEBI:37659) has role plant metabolite (CHEBI:76924)
oleanolic acid (CHEBI:37659) is a hydroxy monocarboxylic acid (CHEBI:35868)
oleanolic acid (CHEBI:37659) is a pentacyclic triterpenoid (CHEBI:25872)
oleanolic acid (CHEBI:37659) is conjugate acid of oleanolate (CHEBI:82828)
Incoming 3β,6β,23-trihydroxyolean-12-en-28-oic acid (CHEBI:69369) has functional parent oleanolic acid (CHEBI:37659)
4-epihederagenin (CHEBI:69528) has functional parent oleanolic acid (CHEBI:37659)
acutoside A (CHEBI:65370) has functional parent oleanolic acid (CHEBI:37659)
gypsogenin (CHEBI:5580) has functional parent oleanolic acid (CHEBI:37659)
hederagenin (CHEBI:69579) has functional parent oleanolic acid (CHEBI:37659)
oleanolic acid 3-O-β-D-glucosiduronic acid (CHEBI:37658) has functional parent oleanolic acid (CHEBI:37659)
oleanolic acid 3-O-[O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside] (CHEBI:66818) has functional parent oleanolic acid (CHEBI:37659)
protobassic acid (CHEBI:73086) has functional parent oleanolic acid (CHEBI:37659)
spathodic acid (CHEBI:69529) has functional parent oleanolic acid (CHEBI:37659)
spinosic acid A (CHEBI:39212) has functional parent oleanolic acid (CHEBI:37659)
oleanolate (CHEBI:82828) is conjugate base of oleanolic acid (CHEBI:37659)
IUPAC Name
3β-hydroxyolean-12-en-28-oic acid
Synonyms Sources
3beta-Hydroxyolean-12-en-28-oic acid KEGG COMPOUND
Astrantiagenin C ChemIDplus
Astrantiagenin C KEGG COMPOUND
Caryophyllin ChemIDplus
Caryophyllin KEGG COMPOUND
Giganteumgenin C ChemIDplus
Oleanic acid ChemIDplus
Virgaureagenin B ChemIDplus
Database Links Databases
C17148 KEGG COMPOUND
Oleanolic_acid Wikipedia
View more database links
Registry Numbers Types Sources
508-02-1 CAS Registry Number KEGG COMPOUND
508-02-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15541359 PubMed citation Europe PMC
24393202 PubMed citation Europe PMC
Last Modified
23 October 2015