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Showing Compound ent-Epicatechin (FDB017126)

Record Information
Version1.0
Creation date2010-04-08 22:12:51 UTC
Update date2019-11-26 03:14:15 UTC
Primary IDFDB017126
Secondary Accession Numbers
  • FDB002576
Chemical Information
FooDB Nameent-Epicatechin
Description(+)-Epicatechin, also known as ent-epicatechin, belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol (+)-Epicatechin is found, on average, in the highest concentration within pears (Pyrus communis) (+)-Epicatechin has also been detected, but not quantified in, several different foods, such as star fruits (Averrhoa carambola), red tea, common buckwheats (Fagopyrum esculentum), apples (Malus pumila), and asian pears (Pyrus pyrifolia). This could make (+)-epicatechin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (+)-Epicatechin.
CAS Number35323-91-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(2S,3S)-3',4',5,7-Tetrahydroxyflavan-3-olChEBI
(2S,3S)-3,3',4',5,7-PentahydroxyflavanChEBI
ent-EpicatechinChEBI
(+)-cis-3,3',4',5,7-PentahydroxyflavanHMDB
(+)-EpicatecholHMDB
(2S,3S)-(+)-EpicatechinHMDB
(2S-cis)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triolHMDB
Catechin CHMDB
D-EpicatechinHMDB
(+)-Epicatechinmanual
(2S-cis)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-Benzopyran-3,5,7-triolmanual
3,3',4',5,7-Pentahydroxyflavan; (+)-cis-formdb_source
3,3',4',5,7-Pentahydroxyflavan; (2S,3S)-formdb_source
d-Epicatechinmanual
Predicted Properties
PropertyValueSource
Water Solubility0.64 g/LALOGPS
logP1.02ALOGPS
logP1.8ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74 m³·mol⁻¹ChemAxon
Polarizability28.39 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H14O6
IUPAC name(2S,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
InChI IdentifierInChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m0/s1
InChI KeyPFTAWBLQPZVEMU-ZFWWWQNUSA-N
Isomeric SMILESO[C@H]1CC2=C(O[C@H]1C1=CC=C(O)C(O)=C1)C=C(O)C=C2O
Average Molecular Weight290.2681
Monoisotopic Molecular Weight290.07903818
Classification
Description Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechins
Alternative Parents
Substituents
  • Catechin
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Ether
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 62.07%; H 4.86%; O 33.07%DFC
Melting PointMp 235-237°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +59 (c, 2 in Me2CO aq.)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSEpicatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-0940000000-635a87e4fbbe005b1b88Spectrum
Predicted GC-MSEpicatechin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-3130069000-ca0968505fc89dd82640Spectrum
Predicted GC-MSEpicatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpicatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-052r-0980000000-b5cee6aae1e7952a7d9f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0079-0900000000-9a4ec6a24f97ad3fd9f22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-0900000000-c152f224fc3c49acdeb52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-007c-0920000000-91de0a80259cfbc0113b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00dr-0900000000-437372b0d194754905ce2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0g6r-0900000000-5069537b6f392aae0fe12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0590000000-516859cd7060b2bf898b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000i-0910000000-7236013988c20252d8c72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0079-0900000000-9afe75272afab175f8892021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-01bi-2900000000-56fefff3a8f788f1a1ca2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-0490000000-1b85894a81aba913bda32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0490000000-80c202adef30df74053b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0910000000-fd8f0d6d6ee1a117d9942021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-007c-0920000000-ca2ff9eca6136f481a1d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0690000000-31f869b582ff052495f72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0079-0910000000-7c1c4c01e56414dde3182021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-0590000000-b3372a9dc6a409ae89982021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0079-0900000000-9731a6caadd423aea0a12021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-52e8123f5ed55bc479622016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0940000000-cfcd9b4e416f64a269162016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-2910000000-be77474275eeee51824b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-f6afeb92914fea4cf8de2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0690000000-76f0c4a6b193c78824c12021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-1940000000-cc596c4cbd5f45583cb12021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0590000000-aff1c3cc94786f87cacf2016-08-03View Spectrum
NMRNot Available
ChemSpider ID158494
ChEMBL IDCHEMBL129482
KEGG Compound IDC09728
Pubchem Compound ID182232
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID147
DrugBank IDNot Available
HMDB IDHMDB37954
CRC / DFC (Dictionary of Food Compounds) IDCML31-M:KWF80-Y
EAFUS IDNot Available
Dr. Duke ID(+)-EPICATECHIN
BIGG IDNot Available
KNApSAcK IDC00000957
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCatechin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
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— 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).