Hyperforin (CED0006122)

Record Information
Version1.0
Creation Date2016-05-25 21:43:24 UTC
Update Date2026-05-14 17:19:55 UTC
Accession NumberCHEM024473
Identification
Common NameHyperforin
ClassSmall Molecule
Description
Hyperforin is a compound with the chemical formula C35H52O4. Hyperforin belongs to the monoterpenoids, a subclass of prenol lipids within the organic compounds. With an average molecular weight of 536.78 g/mol, Hyperforin is a heavy molecule. This compound is found in or released from 15 recorded sources across several sectors. These include electrical and electronic equipment, specifically batteries, capacitors, printed circuit boards, wires and cables, and cell phones, as well as two additional sources in that category. It is present in healthcare, pharmaceuticals and veterinary products, including medical devices and antibiotics. In the textiles, leather and furnishings sector, it is found in synthetic textiles and carpets and rugs. Other recorded sources include food packaging within the food, food processing and cookware sector, and lubricants within both the industrial manufacturing and chemical processing sector and the energy, oil and gas sector, along with one more sector. Recorded exposure routes for the compound include oral, touch, and inhalation. Hyperforin interacts with four recorded protein targets. It acts as an inhibitor of the nuclear receptor subfamily 1 group I member 2 (NR1I2). Additionally, its protein targets include glycogen phosphorylase, muscle form (PYGM), polyunsaturated fatty acid 5-lipoxygenase (ALOX5), and prostaglandin G/H synthase 1 (PTGS1).
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
Synonyms
ValueSource
HiperforinaHMDB
HyperforineHMDB
TetrahydrohyperforinMeSH
HyperforinMeSH
OctahydrohyperforinMeSH
Chemical FormulaC35H52O4
Average Molecular Mass536.785 g/mol
Monoisotopic Mass536.387 g/mol
CAS Registry Number11079-53-1
IUPAC Name4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione
Traditional Name4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione
SMILESCC(C)C(=O)C12C(=O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC(CC=C(C)C)C1(C)CCC=C(C)C)C2=O
InChI IdentifierInChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3
InChI KeyKGSZHKRKHXOAMG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • Cyclohexenone
  • Vinylogous acid
  • Ketone
  • Enol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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 Solubility0.0006 g/LALOGPS
logP6.32ALOGPS
logP9.67ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)7.17ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity166.68 m³·mol⁻¹ChemAxon
Polarizability63.57 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00r6-4000930000-825d03e60688d4164a5aNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-014u-4000090000-3b2edbe576aea2691dc3Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kv-1000970000-f2d0d65c1c9da4e4ebf0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01c3-2100910000-4c97bac428459f6888d6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00w9-4000910000-cea52679bfe4f0206e97Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0000290000-ba844ea9b95ec2277091Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-2001930000-17b477c8431441d95b25Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06fr-4006910000-97256b2da606e4828749Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0002690000-f52d4692efd457221773Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02ka-1001910000-80c7a8f4d910524755eeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9212100000-c91676d622c604ec245aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0000090000-f7f0e1000f74112922bbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0000490000-40e67ced1f26d36df49bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052b-9007600000-97ef903a1bc75b26f93fNot 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
3880.0Log mg/kg[2200:6900]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
306AntibioticsHealthcare, 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
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Thioredoxin, mitochondrial structureClick to view 3D structureThioredoxin, mitochondrialQ99757HumansPredicted (SEA)0.856341
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)794.373
CD81 antigen structureClick to view 3D structureCD81 antigenP60033HumansPredicted (SEA)1.47914
Macrophage scavenger receptor types I and II structureClick to view 3D structureMacrophage scavenger receptor types I and IIP21757HumansPredicted (SEA)1.40129
Click to view 3D structureLanosterol synthaseQ04782YeastPredicted (SEA)2.17978
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)1594.59
Click to view 3D structureTransient receptor potential cation channel subfamily A member 1Q6RI86Rattus norvegicusPredicted (SEA)793.284
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)3283.06
Click to view 3D structurePhospholipase A2 alphaP00623Crotalus adamanteusPredicted (SEA)1.94623
Histone acetyltransferase p300 structureClick to view 3D structureHistone acetyltransferase p300Q09472HumansPredicted (SEA)998.728
Histone acetyltransferase KAT2B structureClick to view 3D structureHistone acetyltransferase KAT2BQ92831HumansPredicted (SEA)304.468
Cathepsin B structureClick to view 3D structureCathepsin BP07858HumansPredicted (SEA)3213.38
Cathepsin G structureClick to view 3D structureCathepsin GP08311HumansPredicted (SEA)1449.55
Click to view 3D structureTransient receptor potential cation channel subfamily M member 8Q8R455Rattus norvegicusPredicted (SEA)441.794
Hepatocyte growth factor receptor structureClick to view 3D structureHepatocyte growth factor receptorP08581HumansPredicted (SEA)6713.48
Click to view 3D structureProstaglandin G/H synthase 1P05979Ovis ariesPredicted (SEA)2518.42
Prostaglandin E synthase structureClick to view 3D structureProstaglandin E synthaseO14684HumansPredicted (SEA)6.07224
DNA polymerase lambda structureClick to view 3D structureDNA polymerase lambdaQ9UGP5HumansPredicted (SEA)0.233548
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)159.513
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)197.659
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial structureClick to view 3D structureDihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrialP10515HumansPredicted (SEA)0.622794
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)885.068
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)335.374
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)46.1646
Click to view 3D structureSerine palmitoyltransferase small subunit BQ8NFR3HumansPredicted (SEA)0.856341
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0030463
FooDB IDFDB002332
Phenol Explorer IDNot Available
KNApSAcK IDC00034542
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHyperforin
Chemspider ID3535
ChEBI ID5834
PubChem Compound ID3662
Kegg Compound IDC07608
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hammer KD, Hillwig ML, Solco AK, Dixon PM, Delate K, Murphy PA, Wurtele ES, Birt DF: Inhibition of prostaglandin E(2) production by anti-inflammatory hypericum perforatum extracts and constituents in RAW264.7 Mouse Macrophage Cells. J Agric Food Chem. 2007 Sep 5;55(18):7323-31. Epub 2007 Aug 15.
2. Sun F, Liu JY, He F, Liu Z, Wang R, Wang DM, Wang YF, Yang DP: In-vitro antitumor activity evaluation of hyperforin derivatives. J Asian Nat Prod Res. 2011 Aug;13(8):688-99. doi: 10.1080/10286020.2011.584532.
3. Hubner AT: Treatment with Hypericum perforatum L. does not trigger decreased resistance in Staphylococcus aureus against antibiotics and hyperforin. Phytomedicine. 2003 Mar;10(2-3):206-8.
4. Muruganandam AV, Bhattacharya SK, Ghosal S: Antidepressant activity of hyperforin conjugates of the St. John's wort, Hypericum perforatum Linn.: an experimental study. Indian J Exp Biol. 2001 Dec;39(12):1302-4.
5. Chatterjee SS, Bhattacharya SK, Wonnemann M, Singer A, Muller WE: Hyperforin as a possible antidepressant component of hypericum extracts. Life Sci. 1998;63(6):499-510.
6. Moore LB, Goodwin B, Jones SA, Wisely GB, Serabjit-Singh CJ, Willson TM, Collins JL, Kliewer SA: St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor. Proc Natl Acad Sci U S A. 2000 Jun 20;97(13):7500-2.
7. Leuner K, Kazanski V, Muller M, Essin K, Henke B, Gollasch M, Harteneck C, Muller WE: Hyperforin--a key constituent of St. John's wort specifically activates TRPC6 channels. FASEB J. 2007 Dec;21(14):4101-11. Epub 2007 Jul 31.
8. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
9. 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.
10. 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.
11. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
12. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
13. The lipid handbook with CD-ROM