Showing Compound Card for Epicatechin (CDB004928)

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Record Information
Version1.0
Created at2020-04-17 18:51:26 UTC
Updated at2020-11-18 16:39:01 UTC
CannabisDB IDCDB004928
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameEpicatechin
DescriptionEpicatechin, also known as alpha-catechin or epicatechol, 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 a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Epicatechin is found, on average, in the highest concentration within a few different foods, such as chocolates, cocoa beans, and cocoa powders and in a lower concentration in strawberries, apricots, and hot chocolates. Epicatechin has also been detected, but not quantified in, several different foods, such as chickpea, corns, garden tomato, watermelons, and colorado pinyons. This could make epicatechin a potential biomarker for the consumption of these foods. A catechin with (2R,3R)-configuration. Epicatechin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-EpicatechinHMDB
(-)-EpicatecholHMDB
(2R,3R)-(-)-EpicatechinHMDB
3,3',4',5,7-PentahydroxyflavaneHMDB
alpha-CatechinHMDB
EpicatecholHMDB
EpigallocatechinHMDB
L(-)-EpicatechinHMDB
L-AcacatechinHMDB
L-EpicatechinHMDB
L-EpicatecholHMDB
3,3',4',5,7-FlavanpentolHMDB
Cyanidanol 3HMDB
Cyanidanol-3HMDB
(+)-CatechinHMDB
(+)-CyanidanolHMDB
Acid, catechuicHMDB
CianidanolHMDB
Acid, catechinicHMDB
CatechinHMDB
Catechinic acidHMDB
Catechuic acidHMDB
CatergenHMDB
KB-53HMDB
ZymaHMDB
(+)-Cyanidanol-3HMDB
KB 53HMDB
Epi-catechinHMDB
EpicatechinPhytoBank
Chemical FormulaC15H14O6
Average Molecular Weight290.27
Monoisotopic Molecular Weight290.079
IUPAC Name(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Nameent-epicatechin
CAS Registry Number490-46-0
SMILES
O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=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-/m1/s1
InChI KeyPFTAWBLQPZVEMU-UKRRQHHQSA-N
Chemical Taxonomy
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

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point240 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability28.13 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSEpicatechin, non-derivatized, GC-MS Spectrumsplash10-014i-0649000000-e7a2620a4d8b1c243de3Spectrum
GC-MSEpicatechin, non-derivatized, GC-MS Spectrumsplash10-014i-0649000000-e7a2620a4d8b1c243de3Spectrum
GC-MSEpicatechin, non-derivatized, GC-MS Spectrumsplash10-014i-0749000000-89375330724a4ecb82cfSpectrum
Predicted GC-MSEpicatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-0940000000-3790a10ce8b93dcb9236Spectrum
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
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000f-1690000000-16c536adc2a6e03c5b4f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1910000000-92d64d3194a12735e5312012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-5900000000-1ec541b64eecd72f35512012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-0006-0090000000-53e575c7acf970449e842012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0079-0900000000-1c23cf9e8aa258a986ad2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052r-1970000000-02212cd1c44e06d5add32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-002r-0090060010-fa16cfeadd4bc0a05e532017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-05bk-0950000000-741428eb8454f83974a02017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090000000-6531ef6ba99afaf524252017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-6531ef6ba99afaf524252017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-002r-0090060010-fa16cfeadd4bc0a05e532017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-05bk-0950000000-741428eb8454f83974a02017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090000000-6531ef6ba99afaf524252017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090000000-556ed7e0a7c3d19ecd862017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001l-0071900002-461eb0f7b0e90ba28a372017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-000i-0910000000-536acb5c7ec5ce972a4d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0f9j-0970000000-6160314e88b9fecac1282017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-faedef1b08ce5b70459b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000j-0290000000-5e7b957db3c3dc34b50c2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0590000000-aff1c3cc94786f87cacf2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0920000000-5e84c0d9207a0a018ab42017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-4900000000-3e525d17e0b05647387a2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-52e8123f5ed55bc479622017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0940000000-cfcd9b4e416f64a269162017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-2910000000-be77474275eeee51824b2017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001871
DrugBank IDDB12039
Phenol Explorer Compound ID125
FoodDB IDFDB003761
KNApSAcK IDC00000956
Chemspider ID65230
KEGG Compound IDC09727
BioCyc IDCPD-7630
BiGG IDNot Available
Wikipedia LinkCatechin
METLIN ID3420
PubChem Compound72276
PDB IDNot Available
ChEBI ID90
References
General ReferencesNot Available