Parthenolide (CED0004058)

Record Information
Version1.0
Creation Date2016-05-22 04:27:33 UTC
Update Date2026-05-14 19:29:26 UTC
Accession NumberCHEM017552
Identification
Common NameParthenolide
ClassSmall Molecule
Description
Parthenolide is an organic compound with the formula C15H20O3 and an average molecular weight of 248.32 g/mol. Parthenolide belongs to the terpene lactones, a subclass of prenol lipids within the organic compounds. Industrially, the substance is used as a conditioner and softener. The compound is found in or released from 13 recorded sources across several sectors. These include electrical and electronic equipment, such as batteries, capacitors, printed circuit boards, wires and cables, and cell phones. It is also present in food packaging within the food, food processing and cookware sector, and in medical devices within the healthcare, pharmaceuticals and veterinary products sector. Additionally, it is found in lubricants used in energy, oil and gas, as well as industrial manufacturing and chemical processing. Other sources include carpets, rugs, and synthetic textiles within the textiles, leather and furnishings sector, among one other sector. Recorded routes of exposure include oral, inhalation, and touch. Parthenolide interacts with six recorded protein targets. It acts as an inhibitor of Inhibitor of nuclear factor kappa-B kinase subunit beta (IKBKB), Nuclear factor NF-kappa-B p105 subunit (NFKB1), Nuclear factor NF-kappa-B p100 subunit (NFKB2), and Transcription factor p65 (RELA), in addition to two other proteins.
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Parthenolide, (1ar-(1ar*,4E,7as*,10as*,10br*))-isomerMeSH
Chemical FormulaC15H20O3
Average Molecular Mass248.322 g/mol
Monoisotopic Mass248.141 g/mol
CAS Registry Number20554-84-1
IUPAC Name(1S,2S,4R,7Z,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one
Traditional Nameparthenolide
SMILES[H]\C1=C(C)\CC[C@@]2([H])C(=C)C(=O)O[C@]2([H])[C@]2([H])O[C@]2(C)CC1
InChI IdentifierInChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5-/t11-,12-,13-,15+/m0/s1
InChI KeyKTEXNACQROZXEV-QLIGOWBFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGermacranolides and derivatives
Alternative Parents
Substituents
  • Germacranolide
  • Germacrane sesquiterpenoid
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • 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
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 Solubility0.2 g/LALOGPS
logP3.03ALOGPS
logP3.07ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.83 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.55 m³·mol⁻¹ChemAxon
Polarizability27.03 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0190000000-2684c1a3def8a4a69519Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002b-3790000000-8a7aea26cf89a7dd3c20Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uxu-9200000000-455b7641ab6a4f2dd513Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-e731516f7092e30f24f4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6t-0190000000-ad0cc1643ecd2864122eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zi1-9610000000-42285f97b7fa82676424Not 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
922.0Log mg/kg[520:1600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & 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
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
Pathways
1 pathway
Parthenolide Drug Metabolism Action Pathway
Parthenolide Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)28.415
Ubiquitin-conjugating enzyme E2 D3 structureClick to view 3D structureUbiquitin-conjugating enzyme E2 D3P61077HumansPredicted (SEA)0.233548
Ubiquitin carboxyl-terminal hydrolase 7 structureClick to view 3D structureUbiquitin carboxyl-terminal hydrolase 7Q93009HumansPredicted (SEA)0.311397
Click to view 3D structureNitric oxide synthase, inducibleP29477Mus musculusPredicted (SEA)6.30579
Toll-like receptor 4 structureClick to view 3D structureToll-like receptor 4O00206HumansPredicted (SEA)0.622794
NACHT, LRR and PYD domains-containing protein 3 structureClick to view 3D structureNACHT, LRR and PYD domains-containing protein 3Q96P20HumansPredicted (SEA)21.0193
Click to view 3D structureTranscriptional activator MybP01103Gallus gallusPredicted (SEA)0.544945
Taste receptor type 2 member 46 structureClick to view 3D structureTaste receptor type 2 member 46P59540HumansPredicted (SEA)0.155698
Pyruvate kinase PKM structureClick to view 3D structurePyruvate kinase PKMP14618HumansPredicted (SEA)22.9655
Ferritin heavy chain structureClick to view 3D structureFerritin heavy chainP02794HumansPredicted (SEA)0.155698
Click to view 3D structureNACHT, LRR and PYD domains-containing protein 3Q8R4B8Mus musculusPredicted (SEA)83.143
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)1665.12
G-protein coupled receptor 55 structureClick to view 3D structureG-protein coupled receptor 55Q9Y2T6HumansPredicted (SEA)1426.98
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)4403.77
Histone deacetylase 3 structureClick to view 3D structureHistone deacetylase 3O15379HumansPredicted (SEA)2903.7
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)4594.82
Histone deacetylase 2 structureClick to view 3D structureHistone deacetylase 2Q92769HumansPredicted (SEA)3673.24
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)322.841
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)1719.77
Signal transducer and activator of transcription 3 structureClick to view 3D structureSignal transducer and activator of transcription 3P40763HumansPredicted (SEA)2418.39
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)2344.66
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)1010.64
Click to view 3D structureGlycine receptor subunit alpha-2P22771Rattus norvegicusPredicted (SEA)0.622794
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)2304.96
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)73.0226
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkParthenolide
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5420805
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References