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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:51 UTC
Update Date2020-09-27 17:41:47 UTC
HMDB IDHMDB0002395
Secondary Accession Numbers
  • HMDB02395
Metabolite Identification
Common NameUrsolic acid
DescriptionUrsolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. Ursolic acid (UA), a pentacyclic triterpene acid, has been isolated from many kinds of medicinal plants, such as Eriobotrya japonica, Rosmarinns officinalis, Melaleuca leucadendron, Ocimum sanctum and Glechoma hederaceae. UA has been reported to produce antitumor activities and antioxidant activity, and is reported to have an antioxidant activity. UA may play an important role in regulating the apoptosis induced by high glucose presumably through scavenging of ROS (reactive oxygen species). It has been found recently that ursolic acid treatment affects growth and apoptosis in cancer cells. (PMID: 15994040 , 17516235 , 17213663 ).
Structure
Data?1601228507
Synonyms
ValueSource
(3beta)-3-Hydroxyurs-12-en-28-oic acidChEBI
MalolChEBI
PrunolChEBI
UrsonChEBI
(3b)-3-Hydroxyurs-12-en-28-oateGenerator
(3b)-3-Hydroxyurs-12-en-28-oic acidGenerator
(3beta)-3-Hydroxyurs-12-en-28-oateGenerator
(3β)-3-Hydroxyurs-12-en-28-oateGenerator
(3β)-3-Hydroxyurs-12-en-28-oic acidGenerator
UrsolateGenerator
(3beta)-3-Hydroxy-urs-12-en-28-oateHMDB
(3beta)-3-Hydroxy-urs-12-en-28-oic acidHMDB
3beta-Hydroxy-12-ursen-28-ic acidHMDB
3beta-Hydroxy-urs-12-en-28-oateHMDB
3beta-Hydroxy-urs-12-en-28-oic acidHMDB
3beta-Hydroxyurs-12-en-28-oateHMDB
3beta-Hydroxyurs-12-en-28-oic acidHMDB
3-Epi-ursolic acidMeSH, HMDB
MerotaineMeSH, HMDB
(+)-Ursolic acidHMDB
3β-Hydroxyurs-12-en-28-oic acidHMDB
Ursolic acidHMDB
beta-Ursolic acidHMDB
β-Ursolic acidHMDB
Bungeolic acidPhytoBank
UrsolisomePhytoBank
UAPhytoBank
Chemical FormulaC30H48O3
Average Molecular Weight456.711
Monoisotopic Molecular Weight456.360345406
IUPAC Name(1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
Traditional Nameursolic acid
CAS Registry Number77-52-1
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
InChI Identifier
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
InChI KeyWCGUUGGRBIKTOS-GPOJBZKASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00059 g/LALOGPS
logP6.35ALOGPS
logP6.58ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)4.74ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity133.7 m³·mol⁻¹ChemAxon
Polarizability54.51 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0ue9-2941000000-2ca89e826b7fdd2c8c1cSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ue9-2941000000-2ca89e826b7fdd2c8c1cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-0023900000-43b07991e5cfcd6c9419Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0079-1000190000-a9eb6c04f4325a25f377Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0000930000-25139768b4507e334b4aSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0000900000-3ad5cc2bdb4d3808c5b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0000900000-63b4335e8110c54aba6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0a4i-0000900000-b6287e2cceb1071deab7Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0000900000-27e80ae2f29ac7c2825cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0a4i-0000900000-433a030e07383bf9ecbfSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0000900000-315a19254ceeb5598e13Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0000900000-2eff827266b9664aa7cfSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0000900000-ff12fe00efc56275c007Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014l-0001223390-7f53534d3578e8cfc4b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0000900000-3ad5cc2bdb4d3808c5b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0000900000-63b4335e8110c54aba6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0000900000-b6287e2cceb1071deab7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0000900000-27e80ae2f29ac7c2825cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0000900000-433a030e07383bf9ecbfSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-01t9-0029800000-86a594c11680cf4a317fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0001211390-507a9b205eaa7310f0ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0037900000-08b9c68893f80ab994c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0w9u-0001223691-a434f7aa9337860104e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0001900000-147d46bee2af34cb0e9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vx-1005900000-1032db86d8a91ecc2551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-055f-9468500000-8b9923090e53d44a56bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-018366f20c7fedd5f9d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fu-0003900000-ef66d040d6b775abb94eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-2008900000-0691b4da8771672d1defSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014373
KNApSAcK IDC00003558
Chemspider ID58472
KEGG Compound IDC08988
BioCyc IDCPD-14496
BiGG IDNot Available
Wikipedia LinkUrsolic acid
METLIN IDNot Available
PubChem Compound64945
PDB IDNot Available
ChEBI ID9908
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Liu J: Oleanolic acid and ursolic acid: research perspectives. J Ethnopharmacol. 2005 Aug 22;100(1-2):92-4. [PubMed:15994040 ]
  2. Oh CJ, Kil IS, Park CI, Yang CH, Park JW: Ursolic acid regulates high glucose-induced apoptosis. Free Radic Res. 2007 Jun;41(6):638-44. [PubMed:17516235 ]
  3. Achiwa Y, Hasegawa K, Udagawa Y: Regulation of the phosphatidylinositol 3-kinase-Akt and the mitogen-activated protein kinase pathways by ursolic acid in human endometrial cancer cells. Biosci Biotechnol Biochem. 2007 Jan;71(1):31-7. Epub 2007 Jan 7. [PubMed:17213663 ]