CHEBI:9908 - ursolic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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.
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
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
InChIKey WCGUUGGRBIKTOS-GPOJBZKASA-N
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)
ursolic acid (CHEBI:9908) is conjugate acid of ursolate (CHEBI:234081)
Incoming 23-hydroxyursolic acid (CHEBI:67896) has functional parent ursolic acid (CHEBI:9908)
ursolate (CHEBI:234081) is conjugate base of 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
6Q5 PDBeChem
C00003558 KNApSAcK
C08988 KEGG COMPOUND
DB15588 DrugBank
FDB014373 FooDB
HMDB0002395 HMDB
LMPR0106180007 LIPID MAPS
Ursolic_acid Wikipedia
View more database links
Registry Numbers Types Sources
2228563 Reaxys Registry Number Reaxys
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