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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:57 UTC
Update Date2022-03-07 02:52:33 UTC
HMDB IDHMDB0030463
Secondary Accession Numbers
  • HMDB30463
Metabolite Identification
Common NameHyperforin
DescriptionHyperforin is found in alcoholic beverages. Hyperforin is a constituent of Hypericum perforatum (St John's Wort) Hyperforin is a phytochemical produced by some of the members of the plant genus Hypericum, notably Hypericum perforatum (St John's wort). The structure of hyperforin was elucidated by a research group from the Shemyakin Institute of Bio-organic Chemistry (USSR Academy of Sciences in Moscow) and published in 1975. Hyperforin is a prenylated phloroglucinol derivative. Total synthesis of hyperforin has not yet been accomplished, despite attempts by several research groups
Structure
Data?1563861989
Synonyms
ValueSource
HiperforinaHMDB
HyperforineHMDB
TetrahydrohyperforinMeSH
HyperforinMeSH
OctahydrohyperforinMeSH
Chemical FormulaC35H52O4
Average Molecular Weight536.785
Monoisotopic Molecular Weight536.386560152
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
CAS Registry Number11079-53-1
SMILES
CC(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 Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point79 - 80 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-266.29330932474
DeepCCS[M+Na]+241.71630932474
AllCCS[M+H]+230.632859911
AllCCS[M+H-H2O]+229.232859911
AllCCS[M+NH4]+231.932859911
AllCCS[M+Na]+232.332859911
AllCCS[M-H]-246.932859911
AllCCS[M+Na-2H]-249.432859911
AllCCS[M+HCOO]-252.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HyperforinCC(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=O4292.9Standard polar33892256
HyperforinCC(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=O3363.5Standard non polar33892256
HyperforinCC(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=O3124.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hyperforin,1TMS,isomer #1CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(=O)C(C)C)C(=O)C(CC=C(C)C)=C2O[Si](C)(C)C3478.2Semi standard non polar33892256
Hyperforin,1TMS,isomer #2CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(O[Si](C)(C)C)=C(C)C)C(=O)C(CC=C(C)C)=C2O3542.6Semi standard non polar33892256
Hyperforin,2TMS,isomer #1CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(O[Si](C)(C)C)=C(C)C)C(=O)C(CC=C(C)C)=C2O[Si](C)(C)C3500.6Semi standard non polar33892256
Hyperforin,2TMS,isomer #1CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(O[Si](C)(C)C)=C(C)C)C(=O)C(CC=C(C)C)=C2O[Si](C)(C)C3469.5Standard non polar33892256
Hyperforin,1TBDMS,isomer #1CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(=O)C(C)C)C(=O)C(CC=C(C)C)=C2O[Si](C)(C)C(C)(C)C3723.2Semi standard non polar33892256
Hyperforin,1TBDMS,isomer #2CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(O[Si](C)(C)C(C)(C)C)=C(C)C)C(=O)C(CC=C(C)C)=C2O3805.5Semi standard non polar33892256
Hyperforin,2TBDMS,isomer #1CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(O[Si](C)(C)C(C)(C)C)=C(C)C)C(=O)C(CC=C(C)C)=C2O[Si](C)(C)C(C)(C)C3981.8Semi standard non polar33892256
Hyperforin,2TBDMS,isomer #1CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(O[Si](C)(C)C(C)(C)C)=C(C)C)C(=O)C(CC=C(C)C)=C2O[Si](C)(C)C(C)(C)C3846.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hyperforin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00r6-4000930000-825d03e60688d4164a5a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyperforin GC-MS (1 TMS) - 70eV, Positivesplash10-014u-4000090000-3b2edbe576aea2691dc32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyperforin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyperforin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyperforin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyperforin GC-MS ("Hyperforin,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyperforin 10V, Positive-QTOFsplash10-00kv-1000970000-f2d0d65c1c9da4e4ebf02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyperforin 20V, Positive-QTOFsplash10-01c3-2100910000-4c97bac428459f6888d62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyperforin 40V, Positive-QTOFsplash10-00w9-4000910000-cea52679bfe4f0206e972015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyperforin 10V, Negative-QTOFsplash10-000i-0000290000-ba844ea9b95ec22770912015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyperforin 20V, Negative-QTOFsplash10-014i-2001930000-17b477c8431441d95b252015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyperforin 40V, Negative-QTOFsplash10-06fr-4006910000-97256b2da606e48287492015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyperforin 10V, Positive-QTOFsplash10-000i-0002690000-f52d4692efd4572217732021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyperforin 20V, Positive-QTOFsplash10-02ka-1001910000-80c7a8f4d910524755ee2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyperforin 40V, Positive-QTOFsplash10-0006-9212100000-c91676d622c604ec245a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyperforin 10V, Negative-QTOFsplash10-000i-0000090000-f7f0e1000f74112922bb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyperforin 20V, Negative-QTOFsplash10-000i-0000490000-40e67ced1f26d36df49b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyperforin 40V, Negative-QTOFsplash10-052b-9007600000-97ef903a1bc75b26f93f2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002332
KNApSAcK IDC00034542
Chemspider ID3535
KEGG Compound IDC07608
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHyperforin
METLIN IDNot Available
PubChem Compound3662
PDB IDNot Available
ChEBI ID5834
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:17696442 ]
  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. [PubMed:21751836 ]
  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. [PubMed:12725578 ]
  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. [PubMed:12018529 ]
  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. [PubMed:9718074 ]
  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. [PubMed:10852961 ]
  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. [PubMed:17666455 ]
  8. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  12. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  13. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular weight:
77982.595
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular weight:
49761.2
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular weight:
76448.0
References
  1. Tirona RG, Leake BF, Wolkoff AW, Kim RB: Human organic anion transporting polypeptide-C (SLC21A6) is a major determinant of rifampin-mediated pregnane X receptor activation. J Pharmacol Exp Ther. 2003 Jan;304(1):223-8. [PubMed:12490595 ]
General function:
Involved in ATP binding
Specific function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular weight:
174205.6
References
  1. Kast HR, Goodwin B, Tarr PT, Jones SA, Anisfeld AM, Stoltz CM, Tontonoz P, Kliewer S, Willson TM, Edwards PA: Regulation of multidrug resistance-associated protein 2 (ABCC2) by the nuclear receptors pregnane X receptor, farnesoid X-activated receptor, and constitutive androstane receptor. J Biol Chem. 2002 Jan 25;277(4):2908-15. Epub 2001 Nov 12. [PubMed:11706036 ]