Protohypericin (CHEM028268)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:20:20 UTC
Update Date2016-11-09 01:18:39 UTC
Accession NumberCHEM028268
Identification
Common NameProtohypericin
ClassSmall Molecule
DescriptionIsolated from Hypericum perforatum (St. John's Wort). Protohypericin is found in tea, alcoholic beverages, and herbs and spices.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ProtohypericinMeSH
Chemical FormulaC30H18O8
Average Molecular Mass506.459 g/mol
Monoisotopic Mass506.100 g/mol
CAS Registry Number548-03-8
IUPAC Name7,11,13,16,18,22-hexahydroxy-5,24-dimethylheptacyclo[13.11.1.1²,¹⁰.0³,⁸.0¹⁹,²⁷.0²¹,²⁶.0¹⁴,²⁸]octacosa-1(27),2(28),3(8),4,6,10,12,14,16,18,21(26),22,24-tridecaene-9,20-dione
Traditional Name7,11,13,16,18,22-hexahydroxy-5,24-dimethylheptacyclo[13.11.1.1²,¹⁰.0³,⁸.0¹⁹,²⁷.0²¹,²⁶.0¹⁴,²⁸]octacosa-1(27),2(28),3(8),4,6,10,12,14,16,18,21(26),22,24-tridecaene-9,20-dione
SMILESCC1=CC2=C(C(O)=C1)C(=O)C1=C(O)C=C(O)C3=C4C(O)=CC(O)=C5C(=O)C6=C(C=C(C)C=C6O)C(C2=C13)=C45
InChI IdentifierInChI=1S/C30H18O8/c1-9-3-11-19(13(31)5-9)29(37)25-17(35)7-15(33)23-24-16(34)8-18(36)26-28(24)22(21(11)27(23)25)12-4-10(2)6-14(32)20(12)30(26)38/h3-8,31-36H,1-2H3
InChI KeyYLILOANQCQKPOD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPerylenequinones
Sub ClassNot Available
Direct ParentPerylenequinones
Alternative Parents
Substituents
  • Perylenequinone
  • Phenanthrol
  • Phenanthrene
  • Anthracene
  • 1-naphthol
  • 2-naphthol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
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 Solubility0.005 g/LALOGPS
logP3.99ALOGPS
logP8.02ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)11.29ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area155.52 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity140.23 m³·mol⁻¹ChemAxon
Polarizability51.15 ųChemAxon
Number of Rings7ChemAxon
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, Positivesplash10-056r-0100930000-12336cd4cee0283cdc28Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0079-5100059000-a013c10cef25f6b4ee31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000290000-b285ed6a5bbc67d2561eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000590000-b687985249b486ac4934Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-1000900000-59633c5f097a37bebecbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-c055ae27121e2e0cd65aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000190000-70652925180413f71f54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2000910000-c6565155993cc2f93715Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-6ebfacadbc229ed0c1c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000090000-6ebfacadbc229ed0c1c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0000290000-e1e9d557e94689a83a64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000090000-cd3514b49df87a50d72dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000090000-cd3514b49df87a50d72dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-0000900000-7ddadd933a23e5889a23Spectrum
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 IDNot Available
HMDB IDHMDB0034180
FooDB IDFDB012472
Phenol Explorer IDNot Available
KNApSAcK IDC00034650
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4590166
ChEBI IDNot Available
PubChem Compound ID5489488
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.