Record Information
Version1.0
Creation date2010-04-08 22:05:12 UTC
Update date2020-02-24 19:10:24 UTC
Primary IDFDB002014
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFagopyrine
DescriptionFagopyrine 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. Fagopyrine has been detected, but not quantified in, a few different foods, such as breakfast cereal, cereals and cereal products, and common buckwheats (Fagopyrum esculentum). This could make fagopyrine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Fagopyrine.
CAS Number72393-03-4
Structure
Thumb
Synonyms
SynonymSource
1,3,4,6,8,13-Hexahydroxy-10,11-dimethyl-2,5-di-2-piperidinylphenanthro[1,10,9,8-opqra]perylene-7,14-dione, 9ciHMDB
3-Carbomethoxy-rifamycin SHMDB
FagopyrinMeSH
1,3,4,6,8,13-Hexahydroxy-10,11-dimethyl-2,5-di-2-piperidinylphenanthro[1,10,9,8-opqra]perylene-7,14-dione, 9CIdb_source
3-carbomethoxy-rifamycin Sbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP3.83ALOGPS
logP6.5ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)11.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area179.58 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity189.43 m³·mol⁻¹ChemAxon
Polarizability73.63 ųChemAxon
Number of Rings10ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC40H34N2O8
IUPAC name5,7,11,18,22,24-hexahydroxy-13,16-dimethyl-6,23-bis(piperidin-2-yl)octacyclo[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/C40H34N2O8/c1-13-11-17(43)23-25-19(13)20-14(2)12-18(44)24-26(20)28-27(25)29-31(35(45)21(15-7-3-5-9-41-15)37(47)33(29)39(23)49)32-30(28)34(40(24)50)38(48)22(36(32)46)16-8-4-6-10-42-16/h11-12,15-16,41-48H,3-10H2,1-2H3
InChI KeyROFJUMITFMRBRF-UHFFFAOYSA-N
Isomeric SMILESCC1=CC(O)=C2C(=O)C3=C(O)C(C4CCCCN4)=C(O)C4=C3C3=C2C1=C1C(C)=CC(O)=C2C(=O)C5=C(O)C(C6CCCCN6)=C(O)C4=C5C3=C12
Average Molecular Weight670.7066
Monoisotopic Molecular Weight670.231516074
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
  • Anthracene
  • Phenanthrene
  • 2-naphthol
  • 1-naphthol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Piperidine
  • Vinylogous acid
  • Polyol
  • Organoheterocyclic compound
  • Azacycle
  • Secondary aliphatic amine
  • Secondary amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.63%; H 5.11%; N 4.18%; O 19.08%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSFagopyrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-1000009000-d71a85c9a865544c3f02Spectrum
Predicted GC-MSFagopyrine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_2_16, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFagopyrine, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1000009000-cef361c4bd290146a1dc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fl0-5000009000-1ee28e4e7a67b93e97852016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000057000-123fb11ccc37b912b5492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000009000-e5024430000d8b1ce7872016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2000019000-bdea7159d5ee1edfb6782016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fsi-7000039000-d8c4b41ee8eb641d8cbc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000009000-30237d532d79f0fff55c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000009000-ad9f658ba14934926f392021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ul4-2100039000-2013d44db014596c3e0c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000009000-85c3e21d35790c42d0272021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000029000-60e5097011b61158f2f42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gvp-0000098000-847b7db6e38f33cc1aeb2021-09-23View Spectrum
NMRNot Available
ChemSpider ID4589856
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5488537
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30196
CRC / DFC (Dictionary of Food Compounds) IDCCX95-Y:CCX95-Y
EAFUS IDNot Available
Dr. Duke IDFAGOPYRIN
BIGG IDNot Available
KNApSAcK IDNot Available
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
HIV-reverse-transcriptase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
photoactiveDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).