CHEBI:9908 - ursolic acid

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ChEBI Name ursolic acid
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 456.711
Monoisotopic Mass 456.36035
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
SMILES [H][C@@]12[C@@H](C)[C@H](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
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.
Application(s): geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ursolic acid (CHEBI:9908) has parent hydride ursane (CHEBI:35711)
ursolic acid (CHEBI:9908) has role geroprotector (CHEBI:176497)
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)
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
6Q5 PDBeChem
C00003558 KNApSAcK
DB15588 DrugBank
FDB014373 FooDB
HMDB0002395 HMDB
Ursolic_acid Wikipedia
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
Citations Waiting for Citations Types Sources
17516089 PubMed citation Europe PMC
28493531 PubMed citation Europe PMC
30496629 PubMed citation Europe PMC
Last Modified
27 October 2021