Showing metabocard for Ursolic acid (BMDB0002395)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:55:05 UTC
Update Date2020-04-22 15:10:56 UTC
BMDB IDBMDB0002395
Secondary Accession Numbers
  • BMDB02395
Metabolite Identification
Common NameUrsolic acid
DescriptionUrsolic acid, also known as malol or prunol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review a significant number of articles have been published on Ursolic acid.
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 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0ue9-2941000000-2ca89e826b7fdd2c8c1cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ue9-2941000000-2ca89e826b7fdd2c8c1cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-0023900000-43b07991e5cfcd6c9419View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0079-1000190000-a9eb6c04f4325a25f377View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0000930000-25139768b4507e334b4aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0000900000-3ad5cc2bdb4d3808c5b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0000900000-63b4335e8110c54aba6eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0a4i-0000900000-b6287e2cceb1071deab7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0000900000-27e80ae2f29ac7c2825cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0a4i-0000900000-433a030e07383bf9ecbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0000900000-315a19254ceeb5598e13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0000900000-2eff827266b9664aa7cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0000900000-ff12fe00efc56275c007View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014l-0001223390-7f53534d3578e8cfc4b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0000900000-3ad5cc2bdb4d3808c5b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0000900000-63b4335e8110c54aba6eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0000900000-b6287e2cceb1071deab7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0000900000-27e80ae2f29ac7c2825cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0000900000-433a030e07383bf9ecbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-01t9-0029800000-86a594c11680cf4a317fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0001211390-507a9b205eaa7310f0ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0037900000-08b9c68893f80ab994c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0w9u-0001223691-a434f7aa9337860104e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0001900000-147d46bee2af34cb0e9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vx-1005900000-1032db86d8a91ecc2551View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-055f-9468500000-8b9923090e53d44a56bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-018366f20c7fedd5f9d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fu-0003900000-ef66d040d6b775abb94eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-2008900000-0691b4da8771672d1defView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002395
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available