Hypericin (CHEM028335)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:23:11 UTC
Update Date2016-11-09 01:18:40 UTC
Accession NumberCHEM028335
Identification
Common NameHypericin
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC30H16O8
Average Molecular Mass504.443 g/mol
Monoisotopic Mass504.085 g/mol
CAS Registry Number548-04-9
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
Traditional Namehypericin
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
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-0000940000-0d62f6b32901e364142aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-008a-5000049000-92bc0a911d1b58cfc8c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0000090000-e9cd20b64eba34b7fb1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0000590000-d6f4544a5f160b2a5b67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000290000-6394299b12d4be2370c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000690000-a414125d88c1d0a72c3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0000900000-cf0d93c0ba6c563a5028Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-19beb2301902b7490149Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000190000-3347517bb50ff44b3105Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7c-1000910000-47bd0419d45b315930b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-68abf5044d528fcc461fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000090000-68abf5044d528fcc461fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-0000920000-c9ae44cdfd493073d84dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000090000-2f988b9a0dc0ff33b3b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000090000-2f988b9a0dc0ff33b3b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0000920000-5ee63630602ca79b7329Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13014
HMDB IDHMDB0034271
FooDB IDFDB012603
Phenol Explorer IDNot Available
KNApSAcK IDC00002829
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHypericin
Chemspider ID4444511
ChEBI ID5835
PubChem Compound ID5281051
Kegg Compound IDC07606
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Kang BY, Chung SW, Kim TS: Inhibition of interleukin-12 production in lipopolysaccharide-activated mouse macrophages by hpyericin, an active component of Hypericum perforatum. Planta Med. 2001 Jun;67(4):364-6.
2. Butterweck V, Christoffel V, Nahrstedt A, Petereit F, Spengler B, Winterhoff H: Step by step removal of hyperforin and hypericin: activity profile of different Hypericum preparations in behavioral models. Life Sci. 2003 Jun 20;73(5):627-39.
3. Park J, English DS, Wannemuehler Y, Carpenter S, Petrich JW: The role of oxygen in the antiviral activity of hypericin and hypocrellin. Photochem Photobiol. 1998 Oct;68(4):593-7.
4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.