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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:51 UTC
Update Date2021-10-13 04:39:16 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 acidHMDB
MerotaineHMDB
(+)-Ursolic acidHMDB
3Β-hydroxyurs-12-en-28-Oic acidHMDB
beta-Ursolic acidHMDB
Β-ursolic acidHMDB
Bungeolic acidHMDB
UrsolisomeHMDB
UAHMDB
Ursolic acidHMDB
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility182.2 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00059 g/LALOGPS
logP10(6.35) g/LALOGPS
logP10(6.58) g/LChemAxon
logS10(-5.9) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ursolic acid[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)=O3401.4Standard polar33892256
Ursolic acid[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)=O3658.3Standard non polar33892256
Ursolic acid[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)=O3721.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ursolic acid,1TMS,isomer #1C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O)CC[C@H]1C3782.8Semi standard non polar33892256
Ursolic acid,1TMS,isomer #2C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O[Si](C)(C)C)CC[C@H]1C3678.0Semi standard non polar33892256
Ursolic acid,2TMS,isomer #1C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O[Si](C)(C)C)CC[C@H]1C3658.9Semi standard non polar33892256
Ursolic acid,1TBDMS,isomer #1C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O)CC[C@H]1C4006.6Semi standard non polar33892256
Ursolic acid,1TBDMS,isomer #2C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@H]1C3940.8Semi standard non polar33892256
Ursolic acid,2TBDMS,isomer #1C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@H]1C4143.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ursolic acid GC-MS (2 TMS)splash10-0ue9-2941000000-2ca89e826b7fdd2c8c1c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ursolic acid GC-MS (Non-derivatized)splash10-0ue9-2941000000-2ca89e826b7fdd2c8c1c2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ursolic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-0023900000-43b07991e5cfcd6c94192017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ursolic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0079-1000190000-a9eb6c04f4325a25f3772017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ursolic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ursolic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid ESI-TOF , Negative-QTOFsplash10-0a4i-0000930000-25139768b4507e334b4a2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid ESI-TOF 30V, Negative-QTOFsplash10-0a4i-0000900000-3ad5cc2bdb4d3808c5b82017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid ESI-TOF 20V, Negative-QTOFsplash10-0a4i-0000900000-63b4335e8110c54aba6e2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid ESI-TOF 50V, Negative-QTOFsplash10-0a4i-0000900000-b6287e2cceb1071deab72017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid ESI-TOF 10V, Negative-QTOFsplash10-0a4i-0000900000-27e80ae2f29ac7c2825c2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid ESI-TOF 40V, Negative-QTOFsplash10-0a4i-0000900000-433a030e07383bf9ecbf2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , negative-QTOFsplash10-0a4i-0000900000-315a19254ceeb5598e132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , negative-QTOFsplash10-0a4i-0000900000-2eff827266b9664aa7cf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , negative-QTOFsplash10-0a4i-0000900000-ff12fe00efc56275c0072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , negative-QTOFsplash10-014l-0001223390-7f53534d3578e8cfc4b42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid LC-ESI-TOF , negative-QTOFsplash10-0a4i-0000900000-3ad5cc2bdb4d3808c5b82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid LC-ESI-TOF , negative-QTOFsplash10-0a4i-0000900000-63b4335e8110c54aba6e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid LC-ESI-TOF , negative-QTOFsplash10-0a4i-0000900000-b6287e2cceb1071deab72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid LC-ESI-TOF , negative-QTOFsplash10-0a4i-0000900000-27e80ae2f29ac7c2825c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid LC-ESI-TOF , negative-QTOFsplash10-0a4i-0000900000-433a030e07383bf9ecbf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , positive-QTOFsplash10-01t9-0029800000-86a594c11680cf4a317f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , positive-QTOFsplash10-0udi-0001211390-507a9b205eaa7310f0ec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , positive-QTOFsplash10-004i-0037900000-08b9c68893f80ab994c82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , positive-QTOFsplash10-0w9u-0001223691-a434f7aa9337860104e72017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ursolic acid 10V, Positive-QTOFsplash10-052r-0001900000-147d46bee2af34cb0e9e2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ursolic acid 20V, Positive-QTOFsplash10-01vx-1005900000-1032db86d8a91ecc25512017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ursolic acid 40V, Positive-QTOFsplash10-055f-9468500000-8b9923090e53d44a56bf2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ursolic acid 10V, Negative-QTOFsplash10-0a4i-0000900000-018366f20c7fedd5f9d22017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ursolic acid 20V, Negative-QTOFsplash10-08fu-0003900000-ef66d040d6b775abb94e2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ursolic acid 40V, Negative-QTOFsplash10-0005-2008900000-0691b4da8771672d1def2017-06-28Wishart LabView Spectrum
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 IDNot Available
Good Scents IDrw1410531
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 ]