Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin (CHEM032199)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:12:40 UTC
Update Date2016-11-09 01:19:25 UTC
Accession NumberCHEM032199
Identification
Common NameEpicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin
ClassSmall Molecule
DescriptionIsolated from Vaccinium vitis-idaea (cowberry). Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin is found in fruits and lingonberry.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Epicatechin-(4b->8)-epicatechin-(2b->7,4b->8)-catechinGenerator
Epicatechin-(4β->8)-epicatechin-(2β->7,4β->8)-catechinGenerator
Chemical FormulaC45H36O18
Average Molecular Mass864.757 g/mol
Monoisotopic Mass864.190 g/mol
CAS Registry Number114637-81-9
IUPAC Name(1R,5R,6S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol
Traditional Name(1R,5R,6S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol
SMILESO[C@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C1=C(O[C@@]3(OC4=C([C@H]1[C@H]3O)C(O)=CC(O)=C4[C@@H]1[C@@H](O)[C@H](OC3=C1C(O)=CC(O)=C3)C1=CC(O)=C(O)C=C1)C1=CC(O)=C(O)C=C1)C=C2O
InChI IdentifierInChI=1S/C45H36O18/c46-18-10-27(54)33-31(11-18)60-41(16-2-5-21(48)25(52)8-16)39(58)37(33)34-28(55)13-29(56)35-38-36-32(62-45(44(38)59,63-43(34)35)17-3-6-22(49)26(53)9-17)14-23(50)19-12-30(57)40(61-42(19)36)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37+,38+,39+,40+,41+,44+,45+/m0/s1
InChI KeySRWJAXVAWDYXPA-ACNGEOCHSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassBiflavonoids and polyflavonoids
Direct ParentBiflavonoids and polyflavonoids
Alternative Parents
Substituents
  • B-type proanthocyanidin
  • A-type proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Proanthocyanidin
  • Catechin
  • Pyranoflavonoid
  • 3'-hydroxyflavonoid
  • Flavan-3-ol
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavan
  • Pyranochromene
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Catechol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Ketal
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.16 g/LALOGPS
logP3.54ALOGPS
logP4.91ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.62ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area320.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity216.7 m³·mol⁻¹ChemAxon
Polarizability85.1 ųChemAxon
Number of Rings10ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0292-0211003490-5e8202baa406f6e2b809Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r5-0600084940-12702116800f0231763dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0910020120-eb3715bfc9597cc57ec8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0111000290-14f0e1f3d1b46e11e789Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w2j-0920140440-5569684c6657178fce02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-0950000000-537693c7d834b9dd24aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-41b280e1fc4a1866093aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000000590-1bf5402cb6770200c938Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03g0-0120001940-9eca3ded1c03f84a814dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000190-5978ab4e7ddf229ec2b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-0200020890-ade1fcf049b10b7c9d51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-1920000560-2ba5b1ad52b9f8eefac5Spectrum
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 IDHMDB0038857
FooDB IDFDB018296
Phenol Explorer IDNot Available
KNApSAcK IDC00009299
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID10350652
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.