(-)-Epiafzelechin (CHEM024848)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:57:52 UTC
Update Date2016-11-09 01:17:58 UTC
Accession NumberCHEM024848
Identification
Common Name(-)-Epiafzelechin
ClassSmall Molecule
DescriptionA catechin derivative having (2R,3R)-configuration.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R,3R)-EpiafzelechinChEBI
Epi-afzelechinChEBI
EpiafzelechinMeSH
Chemical FormulaC15H14O5
Average Molecular Mass274.269 g/mol
Monoisotopic Mass274.084 g/mol
CAS Registry Number24808-04-6
IUPAC Name(2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Nameepiafzelechin
SMILESO[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C=C1)C=C(O)C=C2O
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
Chemical Taxonomy
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
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 Solubility0.46 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1970000000-97a69c7a45c624cc5456Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-002b-3700890000-ad3a8c90f22f6dcef7bcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004r-0690000000-4da2a1e1b8ae2d109c32Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004r-0690000000-3dda57eb8519237ff1d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004r-0690000000-90138410b48eec3cdf8bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-197f43a10026114cf6e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a59-0910000000-4f271083ff1af2b4a646Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0930000000-fd8af365cba78f21a442Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0490000000-d1cb482bc9fba5c1c77cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-0931dca1f9eede095b91Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000j-0910000000-62c438a216915a5cb1ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-f191f6a8bfb1fdd83316Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0490000000-102c0099b32eb6cf1c1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0920000000-16e90c91e06078017d08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-4900000000-1aa083295b52d9560bf8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-3f6f215ea99c3e0e4777Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0940000000-10a1d2bf91d220a561c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-3910000000-d6da6b34ec8094f8de55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-481c391516faccc36069Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05g0-0970000000-dcc4eab79179a249d464Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-009f-4940000000-776437a8382970f7d1c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-5b1317024b148033f6f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-0970000000-43adfba1cc7d810c20a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-2920000000-8465db94f8820d798074Spectrum
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 IDHMDB0030822
FooDB IDFDB002778
Phenol Explorer IDNot Available
KNApSAcK IDC00008805
BiGG IDNot Available
BioCyc IDCPD-10413
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID391781
ChEBI ID31028
PubChem Compound ID443639
Kegg Compound IDC12128
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21070009
2. Pesca MS, Dal Piaz F, Sanogo R, Vassallo A, Bruzual de Abreu M, Rapisarda A, Germano MP, Certo G, De Falco S, De Tommasi N, Braca A: Bioassay-guided isolation of proanthocyanidins with antiangiogenic activities. J Nat Prod. 2013 Jan 25;76(1):29-35. doi: 10.1021/np300614u. Epub 2012 Dec 26.
3. Xu X, Xie H, Wang Y, Wei X: A-type proanthocyanidins from lychee seeds and their antioxidant and antiviral activities. J Agric Food Chem. 2010 Nov 24;58(22):11667-72. doi: 10.1021/jf1033202. Epub 2010 Oct 22.
4. Bicker J, Petereit F, Hensel A: Proanthocyanidins and a phloroglucinol derivative from Rumex acetosa L. Fitoterapia. 2009 Dec;80(8):483-95. doi: 10.1016/j.fitote.2009.08.015. Epub 2009 Aug 18.
5. Zhang HM, Wang CF, Shen SM, Wang GL, Liu P, Liu ZM, Wang YY, Du SS, Liu ZL, Deng ZW: Antioxidant phenolic compounds from Pu-erh tea. Molecules. 2012 Nov 27;17(12):14037-45. doi: 10.3390/molecules171214037.
6. Yano T, Ohmori K, Takahashi H, Kusumi T, Suzuki K: Unified approach to catechin hetero-oligomers: first total synthesis of trimer EZ-EG-CA isolated from Ziziphus jujuba. Org Biomol Chem. 2012 Oct 14;10(38):7685-8. doi: 10.1039/c2ob26337h.
7. Savitri Kumar N, Maduwantha B Wijekoon WM, Kumar V, Nimal Punyasiri PA, Sarath B Abeysinghe I: Separation of proanthocyanidins isolated from tea leaves using high-speed counter-current chromatography. J Chromatogr A. 2009 May 8;1216(19):4295-302. doi: 10.1016/j.chroma.2008.12.025. Epub 2008 Dec 24.
8. Kpegba K, Agbonon A, Petrovic AG, Amouzou E, Gbeassor M, Proni G, Nesnas N: Epiafzelechin from the root bark of Cassia sieberiana: detection by DART mass spectrometry, spectroscopic characterization, and antioxidant properties. J Nat Prod. 2011 Mar 25;74(3):455-9. doi: 10.1021/np100090e. Epub 2010 Nov 11.
9. Seccon A, Rosa DW, Freitas RA, Biavatti MW, Creczynski-Pasa TB: Antioxidant activity and low cytotoxicity of extracts and isolated compounds from Araucaria angustifolia dead bark. Redox Rep. 2010;15(6):234-42. doi: 10.1179/135100010X12826446921789.
10. Su J, Wu Z, Shen Y, Liu R, Zhang C, Li H, Zhang W: Flavonoids from Daphne giraldii Nitsche. Nat Prod Res. 2008;22(15):1355-8. doi: 10.1080/14786410701768196.
11. Liang YH, Ye M, Yang WZ, Qiao X, Wang Q, Yang HJ, Wang XL, Guo DA: Flavan-3-ols from the rhizomes of Drynaria fortunei. Phytochemistry. 2011 Oct;72(14-15):1876-82. doi: 10.1016/j.phytochem.2011.05.011. Epub 2011 Jul 5.
12. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.