Oleanolic acid (CED0002774)

Record Information
Version1.0
Creation Date2016-05-25 02:58:06 UTC
Update Date2026-04-03 07:02:46 UTC
Accession NumberCHEM021117
Identification
Common NameOleanolic acid
ClassSmall Molecule
Description
Oleanolic acid is a compound with the chemical formula C30H48O3 and an average molecular weight of 456.71 g/mol. Oleanolic acid belongs to the triterpenoids, a subclass of prenol lipids within the organic compounds. This substance has been identified in or released from 34 recorded sources across multiple sectors. Within the healthcare, pharmaceuticals & veterinary products sector, it is associated with medical devices. In the energy, oil & gas sector, it is found in lubricants. It is present in textiles, leather & furnishings, specifically in synthetic textiles as well as carpets and rugs. Sources in the food, food processing & cookware sector include food packaging, food preservation, the preparation of vinegar, the preparation of wine or sparkling wine, and fermentation processes for beer, among three others. Within household cleaning & consumer products, it is linked to perfumes within detergents and soaps, pipe accessories, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and four additional sources. Furthermore, it is found in electrical & electronic equipment, including batteries, printed circuit boards, capacitors, cell phones, wires and cables, and five other sources. There are also three additional sectors where the compound is recorded. Recorded exposure routes for oleanolic acid include inhalation, oral, and touch.
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
Synonyms
ValueSource
3beta-Hydroxyolean-12-en-28-Oic acidChEBI
Astrantiagenin CChEBI
CaryophyllinChEBI
Giganteumgenin CChEBI
Oleanic acidChEBI
Virgaureagenin bChEBI
OleanolateKegg
3b-Hydroxyolean-12-en-28-OateGenerator
3b-Hydroxyolean-12-en-28-Oic acidGenerator
3beta-Hydroxyolean-12-en-28-OateGenerator
3Β-hydroxyolean-12-en-28-OateGenerator
3Β-hydroxyolean-12-en-28-Oic acidGenerator
OleanateGenerator
(3-beta)-3-Hydroxyolean-12-en-28-oateHMDB
(3-beta)-3-Hydroxyolean-12-en-28-oic acidHMDB
(3.beta.)-3-beta-hydroxy-olean-12-en-28-oateHMDB
(3.beta.)-3-beta-hydroxy-olean-12-en-28-oic acidHMDB
(3.beta.)-3-hydroxy-olean-12-en-28-oateHMDB
(3.beta.)-3-hydroxy-olean-12-en-28-oic acidHMDB
(4AS,5S,6as,6BR,8R,8ar,10S,12ar,12BR,14BS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acidHMDB
3-beta-Hydroxyolean-12-en-28-oateHMDB
3-beta-Hydroxyolean-12-en-28-oic acidHMDB
3.beta.-hydroxy-olean-12-en-28-oateHMDB
3.beta.-hydroxy-olean-12-en-28-oic acidHMDB
3beta-Hydroxy-olean-12-en-28-oateHMDB
3beta-Hydroxy-olean-12-en-28-oic acidHMDB
Oleanane triterpenesMeSH, HMDB
Triterpenes, oleananeMeSH, HMDB
OleanolMeSH, HMDB
HederinsMeSH, HMDB
(3beta)-3-Hydroxyolean-12-en-28-oic acidPhytoBank
(3β)-3-Hydroxyolean-12-en-28-oic acidPhytoBank
(+)-Oleanolic acidPhytoBank
Gledigenin 1PhytoBank
Oleonolic acidPhytoBank
OAPhytoBank
Chemical FormulaC30H48O3
Average Molecular Mass456.711 g/mol
Monoisotopic Mass456.360 g/mol
CAS Registry Number508-02-1
IUPAC Name(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-2,2,6a,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 Nameoleanolic acid
SMILESCC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(O)=O
InChI IdentifierInChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1
InChI KeyMIJYXULNPSFWEK-GTOFXWBISA-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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00082 g/LALOGPS
logP7.09ALOGPS
logP6.59ChemAxon
logS-5.8ALOGPS
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
Refractivity133.62 m³·mol⁻¹ChemAxon
Polarizability54.87 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0udi-2951000000-3ffcf6404c28c9072e6eNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0udi-2951000000-3ffcf6404c28c9072e6eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-002f-0014900000-844b76f23b4a02a75c20Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000i-1011190000-4d07cbb48cd57a724a3cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0000900002-a0a4b7ccad94baf5df67Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0000900000-bc55e4c6ed84a38ec6a8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0000900000-6a5c27def3e5639abbbcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0000900000-62f98aa71d39d7185d67Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0000900000-0492f069e415506430f0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0000900000-09b6dab9027bd312a816Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-0001900000-948551e80a675e804945Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01vx-0116900000-a7bbd734cfb389f003ceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001l-3459300000-fe5b4ff0a697d946a205Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0000900000-24b5f92b17a675bd0042Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08fu-0003900000-df302b7b4b1f9bf77cc5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000e-2007900000-2e9882aa899cbe3bd6daNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0000900000-0d11296813b631a2140fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0000900000-a04074ef438068f127bbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0001900000-ec650846439f5cbbb4c2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0000900000-a2106bcf05d5c3dc7defNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-0694700000-aa642e480c6b2dafc5d5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ei-0940000000-67c9b141383d1a95ec29Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2025.0Log mg/kg[1100:3600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
233BrushesPersonal care & cosmeticsNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
496FencingBuilding & ConstructionNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
568Tobacco Product Moisture ControlHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
FUN14 domain-containing protein 1 structureClick to view 3D structureFUN14 domain-containing protein 1Q8IVP5HumansPredicted (SEA)0.0778492
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)0.233548
Tyrosine-protein phosphatase non-receptor type 2 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 2P17706HumansPredicted (SEA)0.0778492
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)0.155698
Aldo-keto reductase family 1 member B10 structureClick to view 3D structureAldo-keto reductase family 1 member B10O60218HumansPredicted (SEA)0.311397
Tissue factor structureClick to view 3D structureTissue factorP13726HumansPredicted (SEA)0.311397
Bile acid receptor structureClick to view 3D structureBile acid receptorQ96RI1HumansPredicted (SEA)1.08989
Click to view 3D structureProteaseQ9YQ12Human immunodeficiency virus 1Predicted (SEA)0.856341
Click to view 3D structureDNA polymerase betaP06766Rattus norvegicusPredicted (SEA)0.0778492
Transcription factor p65 structureClick to view 3D structureTranscription factor p65Q04206HumansPredicted (SEA)0.233548
11-beta-hydroxysteroid dehydrogenase 1 structureClick to view 3D structure11-beta-hydroxysteroid dehydrogenase 1P28845HumansPredicted (SEA)3.26967
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)3.58106
Cholesteryl ester transfer protein structureClick to view 3D structureCholesteryl ester transfer proteinP11597HumansPredicted (SEA)1.32344
Liver carboxylesterase 1 structureClick to view 3D structureLiver carboxylesterase 1P23141HumansPredicted (SEA)4.04816
Click to view 3D structureGlycogen phosphorylase, muscle formP00489Oryctolagus cuniculusPredicted (SEA)0.0778492
Click to view 3D structureCMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1P54751Mus musculusPredicted (SEA)0.700643
Click to view 3D structureBasic phospholipase A2 1P00599Naja melanoleucaPredicted (SEA)0.467095
Click to view 3D structureAcidic phospholipase A2 EC-IQ7T3S7Echis carinatusPredicted (SEA)0.467095
Click to view 3D structureBasic phospholipase A2 PLA-AP59264Trimeresurus flavoviridisPredicted (SEA)0.467095
Click to view 3D structureHemagglutininB4URE7Influenza A virusPredicted (SEA)0.778492
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)4.9045
Click to view 3D structureGlycogen [starch] synthase, liverP54840HumansPredicted (SEA)0.622794
Click to view 3D structureGlucose-6-phosphatase catalytic subunit 1P43428Rattus norvegicusPredicted (SEA)0.622794
Prostaglandin E synthase structureClick to view 3D structureProstaglandin E synthaseO14684HumansPredicted (SEA)5.60514
Solute carrier organic anion transporter family member 1B3 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B3Q9NPD5HumansPredicted (SEA)3.42537
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0002364
FooDB IDFDB013034
Phenol Explorer IDNot Available
KNApSAcK IDC00019064
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOleanolic_acid
Chemspider ID10062
ChEBI ID37659
PubChem Compound ID10494
Kegg Compound IDC17148
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15541359
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24393202
3. Corey, E. J.; Lee, Jaemoon. Enantioselective total synthesis of oleanolic acid, erythrodiol, b-amyrin, and other pentacyclic triterpenes from a common intermediate. Journal of the American Chemical Society (1993), 115(19), 8873-4.
4. Corey, E. J.; Lee, Jaemoon. Enantioselective total synthesis of oleanolic acid, erythrodiol, b-amyrin, and other pentacyclic triterpenes from a common intermediate. Journal of the American Chemical Society (1993), 115(19), 8873-4.
5. Marquez-Martin A, De La Puerta R, Fernandez-Arche A, Ruiz-Gutierrez V, Yaqoob P: Modulation of cytokine secretion by pentacyclic triterpenes from olive pomace oil in human mononuclear cells. Cytokine. 2006 Dec;36(5-6):211-7. Epub 2007 Feb 9.
6. Rodriguez-Rodriguez R, Herrera MD, Perona JS, Ruiz-Gutierrez V: Potential vasorelaxant effects of oleanolic acid and erythrodiol, two triterpenoids contained in 'orujo' olive oil, on rat aorta. Br J Nutr. 2004 Oct;92(4):635-42.
7. Liu J: Oleanolic acid and ursolic acid: research perspectives. J Ethnopharmacol. 2005 Aug 22;100(1-2):92-4.