Record Information
Version1.0
Creation date2010-04-08 22:10:15 UTC
Update date2019-11-26 03:07:10 UTC
Primary IDFDB012603
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHypericin
DescriptionWidespread in Hypericum subspecies especies Hypericum perforatum (St John's Wort) Hypericin is a red-coloured anthraquinone-derivative, which, together with hyperforin, is one of the principal active constituents of Hypericum (Saint John's wort). Hypericin is believed to act as an antibiotic and non-specific kinase inhibitor. Hypericin may inhibit the action of the enzyme dopamine ?-hydroxylase, leading to increased dopamine levels, although thus possibly decreasing norepinephrine and epinephrine. Hypericin is found in tea, alcoholic beverages, and herbs and spices.
CAS Number548-04-9
Structure
Thumb
Synonyms
SynonymSource
1:6:8:10:11:13-Hexahydroxy-3:4-dimethyl-meso-naphthodianthrene-7:14-dioneChEBI
HipericinaChEBI
HypericineChEBI
Hypericum redChEBI
HyperizinChEBI
1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione, 9ciHMDB
4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethylnaphthodianthroneHMDB
Hypericin & visible lightHMDB
Hypericin from hypericum perforatumHMDB
Hypericum extractHMDB
MycoporphyrinHMDB
VimrxynHMDB
mono-(123I)iodohypericinMeSH
1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.0073 g/LALOGPS
logP3.92ALOGPS
logP7.7ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.39ChemAxon
pKa (Strongest Basic)16.11ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area155.52 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity139.31 m³·mol⁻¹ChemAxon
Polarizability50.96 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC30H16O8
IUPAC name5,7,11,18,22,24-hexahydroxy-13,16-dimethyloctacyclo[13.11.1.1²,¹⁰.0³,⁸.0⁴,²⁵.0¹⁹,²⁷.0²¹,²⁶.0¹⁴,²⁸]octacosa-1(27),2(28),3,5,7,10,12,14,16,18,21,23,25-tridecaene-9,20-dione
InChI IdentifierInChI=1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3
InChI KeyBTXNYTINYBABQR-UHFFFAOYSA-N
Isomeric SMILESCC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C4=C3C3=C2C1=C1C(C)=CC(O)=C2C(=O)C5=C(O)C=C(O)C4=C5C3=C12
Average Molecular Weight504.4432
Monoisotopic Molecular Weight504.084517488
Classification
Description Belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPyrenes
Sub ClassBenzopyrenes
Direct ParentBenzopyrenes
Alternative Parents
Substituents
  • Benzo-a-pyrene
  • Benzo-e-pyrene
  • Phenanthro-perylenequinone
  • Perylenequinone
  • Chrysene
  • Triphenylene
  • Phenanthrol
  • Phenanthrene
  • Anthracene
  • 1-naphthol
  • 2-naphthol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Polyol
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.43%; H 3.20%; O 25.37%DFC
Melting PointMp 300° (dec.)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data603 () (Py) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSHypericin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udr-0000940000-0d62f6b32901e364142aSpectrum
Predicted GC-MSHypericin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-008a-5000049000-92bc0a911d1b58cfc8c0Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0000090000-e9cd20b64eba34b7fb1eSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0000590000-d6f4544a5f160b2a5b67Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000290000-6394299b12d4be2370c0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000690000-a414125d88c1d0a72c3dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0000900000-cf0d93c0ba6c563a5028Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-19beb2301902b7490149Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000190000-3347517bb50ff44b3105Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7c-1000910000-47bd0419d45b315930b3Spectrum
NMRNot Available
ChemSpider ID4444511
ChEMBL IDCHEMBL286494
KEGG Compound IDC07606
Pubchem Compound ID5281051
Pubchem Substance IDNot Available
ChEBI ID5835
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34271
CRC / DFC (Dictionary of Food Compounds) IDHJG16-U:HJG16-U
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00002829
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDHypericin
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference