Ursolic acid (CHEM029557)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:14:43 UTC
Update Date2016-11-09 01:18:54 UTC
Accession NumberCHEM029557
Identification
Common NameUrsolic acid
ClassSmall Molecule
DescriptionA pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass456.700 g/mol
Monoisotopic Mass456.360 g/mol
CAS Registry Number77-52-1
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
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)C3CC[C@@]12C)C(O)=O
InChI IdentifierInChI=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-JJWDWEPMSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002395
FooDB IDFDB014373
Phenol Explorer IDNot Available
KNApSAcK IDC00003558
BiGG IDNot Available
BioCyc IDCPD-14496
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkUrsolic acid
Chemspider ID58472
ChEBI ID9908
PubChem Compound ID64945
Kegg Compound IDC08988
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17516089
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=28493531
3. Liu J: Oleanolic acid and ursolic acid: research perspectives. J Ethnopharmacol. 2005 Aug 22;100(1-2):92-4.
4. 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.
5. 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.