Ursolic acid lactone (CHEM030335)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:49:44 UTC
Update Date2016-11-09 01:19:03 UTC
Accession NumberCHEM030335
Identification
Common NameUrsolic acid lactone
ClassSmall Molecule
Description3beta-Hydroxy-28,13-ursanolide is found in herbs and spices. 3beta-Hydroxy-28,13-ursanolide is isolated from Helichrysum italicum (curry plant).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3b-Hydroxy-28,13-ursanolideGenerator
3Β-hydroxy-28,13-ursanolideGenerator
Ursolic acid lactoneHMDB
Chemical FormulaC30H48O3
Average Molecular Mass456.700 g/mol
Monoisotopic Mass456.360 g/mol
CAS Registry Number29428-70-4
IUPAC Name(1S,4S,5R,10S,13R,17S,18R,19S,20R)-10-hydroxy-4,5,9,9,13,19,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-23-one
Traditional Name(1S,4S,5R,10S,13R,17S,18R,19S,20R)-10-hydroxy-4,5,9,9,13,19,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-23-one
SMILES[H][C@@]12[C@@H](C)[C@H](C)CC[C@]11CC[C@]3(C)[C@@]2(CCC2[C@@]4(C)CC[C@H](O)C(C)(C)C4CC[C@@]32C)OC1=O
InChI IdentifierInChI=1S/C30H48O3/c1-18-8-14-29-17-16-28(7)27(6)13-9-20-25(3,4)22(31)11-12-26(20,5)21(27)10-15-30(28,33-24(29)32)23(29)19(18)2/h18-23,31H,8-17H2,1-7H3/t18-,19+,20?,21?,22+,23-,26+,27-,28+,29+,30+/m1/s1
InChI KeyJGZVNQDYYGVIBP-DCIJUUGPSA-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
  • Caprolactone
  • Oxepane
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility6.3e-05 g/LALOGPS
logP5.89ALOGPS
logP6.57ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity130.81 m³·mol⁻¹ChemAxon
Polarizability54.96 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-1042900000-e2c8dd65da30c7ba57b3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03di-2034390000-d313b07a43e3213e482aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0000900000-08021509793f6cfe431dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-2018900000-db62d62ba6e04113cbbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-7119500000-be959b9491ad2eaf8c42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-ece8245e0569254a460eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-0000900000-074b10d69a8b60c03f8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvm-0319600000-16a091705380d6867aa6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-0d11296813b631a2140fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-0d11296813b631a2140fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0000900000-da5da263febfdd7594f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-1e9fb6056c2b99256dedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0535900000-fd040d2ce10d247d1469Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-3962400000-ca6383f7044902af3cfeSpectrum
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 IDHMDB0036675
FooDB IDFDB015605
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014192
ChEBI ID192016
PubChem Compound ID131752032
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM