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Showing Compound (-)-Epiafzelechin (FDB002778)

Record Information
Version1.0
Creation date2010-04-08 22:05:31 UTC
Update date2020-09-17 15:41:01 UTC
Primary IDFDB002778
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-Epiafzelechin
Description(-)-Epiafzelechin belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4. Thus, (-)-epiafzelechin is considered to be a flavonoid lipid molecule (-)-Epiafzelechin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (-)-Epiafzelechin is found, on average, in the highest concentration within tea (-)-Epiafzelechin has also been detected, but not quantified in, fruits and kiwis. This could make (-)-epiafzelechin a potential biomarker for the consumption of these foods. A catechin derivative having (2R,3R)-configuration.
CAS Number24808-04-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(2R,3R)-EpiafzelechinChEBI
Epi-afzelechinChEBI
EpiafzelechinMeSH
(-)-Epiafzelechindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.46 g/LALOGPS
logP1.29ALOGPS
logP2.1ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)9.15ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.02 m³·mol⁻¹ChemAxon
Polarizability27.51 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H14O5
IUPAC name(2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
InChI IdentifierInChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1
InChI KeyRSYUFYQTACJFML-UKRRQHHQSA-N
Isomeric SMILESO[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C=C1)C=C(O)C=C2O
Average Molecular Weight274.2687
Monoisotopic Molecular Weight274.084123558
Classification
Description Belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavan-3-ols
Alternative Parents
Substituents
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavan-3-ol
  • Hydroxyflavonoid
  • 1-benzopyran
  • Chromane
  • Benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 65.69%; H 5.14%; O 29.17%DFC
Melting PointMp 240-243 dec. (312°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -4 (c, 1 in Me2CO)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(-)-Epiafzelechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-1970000000-97a69c7a45c624cc5456Spectrum
Predicted GC-MS(-)-Epiafzelechin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002b-3700890000-ad3a8c90f22f6dcef7bcSpectrum
Predicted GC-MS(-)-Epiafzelechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Epiafzelechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004r-0690000000-4da2a1e1b8ae2d109c322017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004r-0690000000-3dda57eb8519237ff1d32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004r-0690000000-90138410b48eec3cdf8b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-197f43a10026114cf6e72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a59-0910000000-4f271083ff1af2b4a6462021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0930000000-fd8af365cba78f21a4422021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0490000000-d1cb482bc9fba5c1c77c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-0931dca1f9eede095b912021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000j-0910000000-62c438a216915a5cb1cc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-f191f6a8bfb1fdd833162021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0490000000-102c0099b32eb6cf1c1b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0920000000-16e90c91e06078017d082016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-4900000000-1aa083295b52d9560bf82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-3f6f215ea99c3e0e47772016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0940000000-10a1d2bf91d220a561c92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-3910000000-d6da6b34ec8094f8de552016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-481c391516faccc360692021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05g0-0970000000-dcc4eab79179a249d4642021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-009f-4940000000-776437a8382970f7d1c22021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-5b1317024b148033f6f62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-0970000000-43adfba1cc7d810c20a92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-2920000000-8465db94f8820d7980742021-09-24View Spectrum
NMRNot Available
ChemSpider ID391781
ChEMBL IDCHEMBL159303
KEGG Compound IDC12128
Pubchem Compound ID443639
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30822
CRC / DFC (Dictionary of Food Compounds) IDCNP37-T:CNP38-U
EAFUS IDNot Available
Dr. Duke ID(-)-EPIAFZELECHIN
BIGG IDNot Available
KNApSAcK IDC00008805
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
cyclooxygenase-1 inhibitor50630 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.DUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).