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Showing Compound Protohypericin (FDB012472)

Record Information
Version1.0
Creation date2010-04-08 22:10:11 UTC
Update date2019-11-26 03:06:52 UTC
Primary IDFDB012472
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProtohypericin
DescriptionProtohypericin 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. Protohypericin has been detected, but not quantified in, several different foods, such as green tea, red tea, black tea, herbal tea, and alcoholic beverages. This could make protohypericin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Protohypericin.
CAS Number548-03-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC30H18O8
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
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
Isomeric 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
Average Molecular Weight506.4591
Monoisotopic Molecular Weight506.100167552
Classification
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSProtohypericin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056r-0100930000-12336cd4cee0283cdc28Spectrum
Predicted GC-MSProtohypericin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-5100059000-a013c10cef25f6b4ee31Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000290000-b285ed6a5bbc67d2561e2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000590000-b687985249b486ac49342015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-1000900000-59633c5f097a37bebecb2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-c055ae27121e2e0cd65a2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000190000-70652925180413f71f542015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2000910000-c6565155993cc2f937152015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-6ebfacadbc229ed0c1c62021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000090000-6ebfacadbc229ed0c1c62021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0000290000-e1e9d557e94689a83a642021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000090000-cd3514b49df87a50d72d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000090000-cd3514b49df87a50d72d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-0000900000-7ddadd933a23e5889a232021-09-25View Spectrum
NMRNot Available
ChemSpider ID4590166
ChEMBL IDCHEMBL1078768
KEGG Compound IDNot Available
Pubchem Compound ID5489488
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34180
CRC / DFC (Dictionary of Food Compounds) IDHHF88-Y:HHF88-Y
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00034650
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
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