Back to Compounds

Showing Compound Hyperforin (FDB002332)

Record Information
Version1.0
Creation date2010-04-08 22:05:20 UTC
Update date2019-11-26 02:57:20 UTC
Primary IDFDB002332
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHyperforin
DescriptionConstituent 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. Hyperforin is found in tea, alcoholic beverages, and herbs and spices.
CAS Number11079-53-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
HiperforinaHMDB
HyperforineHMDB
TetrahydrohyperforinMeSH
HyperforinMeSH
OctahydrohyperforinMeSH
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
Chemical FormulaC35H52O4
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
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
Isomeric 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
Average Molecular Weight536.785
Monoisotopic Molecular Weight536.386560152
Classification
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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.31%; H 9.76%; O 11.92%DFC
Melting PointMp 79-80°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKa4.8
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]18D +41 (EtOH)DFC
Spectroscopic UV Data298 (e 11000) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSHyperforin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00r6-4000930000-825d03e60688d4164a5aSpectrum
Predicted GC-MSHyperforin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014u-4000090000-3b2edbe576aea2691dc3Spectrum
Predicted GC-MSHyperforin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHyperforin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHyperforin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHyperforin, "Hyperforin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kv-1000970000-f2d0d65c1c9da4e4ebf02015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01c3-2100910000-4c97bac428459f6888d62015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00w9-4000910000-cea52679bfe4f0206e972015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000290000-ba844ea9b95ec22770912015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2001930000-17b477c8431441d95b252015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06fr-4006910000-97256b2da606e48287492015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0002690000-f52d4692efd4572217732021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ka-1001910000-80c7a8f4d910524755ee2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9212100000-c91676d622c604ec245a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000090000-f7f0e1000f74112922bb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000490000-40e67ced1f26d36df49b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-9007600000-97ef903a1bc75b26f93f2021-09-24View Spectrum
NMRNot Available
ChemSpider ID3535
ChEMBL IDNot Available
KEGG Compound IDC07608
Pubchem Compound ID3662
Pubchem Substance IDNot Available
ChEBI ID5834
Phenol-Explorer IDNot Available
DrugBank IDDB01892
HMDB IDHMDB30463
CRC / DFC (Dictionary of Food Compounds) IDCKG82-P:CKG82-P
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00034542
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDHyperforin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Nuclear receptor subfamily 1 group I member 2NR1I2O75469
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference