CHEBI:9908 - ursolic acid

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ChEBI Name ursolic acid
ChEBI ID CHEBI:9908
Definition A pentacyclic triterpenoid that is urs-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/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1
InChIKey WCGUUGGRBIKTOS-GPOJBZKASA-N
SMILES C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@H]1C)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
Rubia yunnanensis (IPNI:765385-1) Found in root (BTO:0001188). Methanolic extract of air dried powdered roots. See: PubMed
Vaccinium macrocarpon (NCBI:txid13750) Found in fruit (BTO:0000486). See: PubMed
Crataegus monogyna (NCBI:txid140997) See: PubMed
Symplocos lancifolia (NCBI:txid239704) Found in leaf (BTO:0000713). Dried, powdered leaves extracted with boiling 80% methanol See: PubMed
Crataegus laevigata (NCBI:txid298643) Commercial herbal preperation See: PubMed
Ficus mucuso (NCBI:txid309328) Found in fruit (BTO:0000486). Methanolic extract of air-dried and powdered figs(fruits) See: PubMed
Eriobotrya japonica (NCBI:txid32224) Found in leaf (BTO:0000713). See: PubMed
Malus domestica (NCBI:txid3750) Found in fruit (BTO:0000486). See: PubMed
Prunus domestica (NCBI:txid3758) Found in fruit (BTO:0000486). See: PubMed
Terminalia catappa (NCBI:txid39993) Found in leaf (BTO:0000713). Chloroform extract of leaves See: PubMed
Rhododendron (NCBI:txid4346) 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
Rhododendron ferrugineum (NCBI:txid49622) Found in leaf (BTO:0000713). MeOH extract of CHCl3 soluble fraction of air-dried,powdered leaves,ursolic & oleanolic acid mixture See: PubMed
Leonurus cardiaca (NCBI:txid587664) Commercial herbal preperation See: PubMed
Vaccinium corymbosum (NCBI:txid69266) Found in fruit (BTO:0000486). See: PubMed
Rosa laevigata (NCBI:txid74652) Found in leaf (BTO:0000713). 70% EtOH extract of dried leaves 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 ursolic acid (CHEBI:9908) has parent hydride ursane (CHEBI:35711)
ursolic acid (CHEBI:9908) has role plant metabolite (CHEBI:76924)
ursolic acid (CHEBI:9908) is a hydroxy monocarboxylic acid (CHEBI:35868)
ursolic acid (CHEBI:9908) is a pentacyclic triterpenoid (CHEBI:25872)
Incoming 23-hydroxyursolic acid (CHEBI:67896) has functional parent ursolic acid (CHEBI:9908)
IUPAC Name
3β-hydroxyurs-12-en-28-oic acid
Synonyms Sources
(3β)-3-hydroxyurs-12-en-28-oic acid ChemIDplus
malol ChemIDplus
prunol ChemIDplus
Ursolic acid KEGG COMPOUND
urson ChemIDplus
Manual Xrefs Databases
C00003558 KNApSAcK
C08988 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
2228563 Reaxys Registry Number Reaxys
2228563 Beilstein Registry Number Beilstein
77-52-1 CAS Registry Number KEGG COMPOUND
77-52-1 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
17516089 PubMed citation Europe PMC
Last Modified
13 April 2015