ent-Epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-arabinoside (CHEM023896)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:21:24 UTC
Update Date2016-11-09 01:17:47 UTC
Accession NumberCHEM023896
Identification
Common Nameent-Epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-arabinoside
ClassSmall Molecule
DescriptionEnt-epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-arabinoside is a member of the class of compounds known as biflavonoids and polyflavonoids. Biflavonoids and polyflavonoids 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''. Ent-epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-arabinoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Ent-epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-arabinoside can be found in cocoa bean, which makes ent-epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-arabinoside a potential biomarker for the consumption of this food product.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ent-Epicatechin-(2a->7,4a->8)-epicatechin 3-arabinosideGenerator
ent-Epicatechin-(2α->7,4α->8)-epicatechin 3-arabinosideGenerator
Chemical FormulaC35H32O16
Average Molecular Mass708.619 g/mol
Monoisotopic Mass708.169 g/mol
CAS Registry Number135077-25-7
IUPAC Name(1S,5R,6R,13R,21S)-5,13-bis(3,4-dihydroxyphenyl)-21-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-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-tetrol
Traditional Name(1S,5R,6R,13R,21S)-5,13-bis(3,4-dihydroxyphenyl)-21-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-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-tetrol
SMILESO[C@H]1CO[C@@H](O[C@H]2[C@H]3C4=C(O[C@@]2(OC2=C3C3=C(C[C@@H](O)[C@H](O3)C3=CC=C(O)C(O)=C3)C(O)=C2)C2=CC=C(O)C(O)=C2)C=C(O)C=C4O)[C@H](O)[C@H]1O
InChI IdentifierInChI=1S/C35H32O16/c36-14-7-21(42)26-24(8-14)50-35(13-2-4-17(38)20(41)6-13)33(49-34-30(46)29(45)23(44)11-47-34)28(26)27-25(51-35)10-18(39)15-9-22(43)31(48-32(15)27)12-1-3-16(37)19(40)5-12/h1-8,10,22-23,28-31,33-34,36-46H,9,11H2/t22-,23+,28+,29+,30-,31-,33+,34+,35-/m1/s1
InChI KeySFVJFSIQKBXNPZ-MIWZTYSMSA-N
Chemical Taxonomy
Description 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
  • A-type proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Proanthocyanidin
  • Catechin
  • Pyranoflavonoid
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavan-3-ol
  • Hydroxyflavonoid
  • Flavan
  • Pyranochromene
  • Glycosyl compound
  • O-glycosyl compound
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Phenol
  • Ketal
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Ether
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Solubility0.4 g/LALOGPS
logP1.97ALOGPS
logP2.45ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.66ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area268.68 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity170.65 m³·mol⁻¹ChemAxon
Polarizability68.62 ųChemAxon
Number of Rings8ChemAxon
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, Positivesplash10-0a6r-0200193200-74b44aea61cf7c09fefcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0300591000-5a1ed6fbefbcd473e45dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1911611000-97ae460b0ad9fdaca0cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1410094800-e923afd15034bca492ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ke9-0900182000-4a2e179235dd17764b70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-6951520000-a9a85ff192f9fcaf0a9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000093700-852ab37c54e0953ba44cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7i-1200389500-6ac739ccbb637eed8fd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-4400749000-74c5d70691c7f264f4c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aor-0200009300-482c43b5afb779cef42cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-8300097400-7138169ce0ef9dd0c4c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-9600256100-7ac4f4a99aac181d3530Spectrum
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 IDNot Available
FooDB IDFDB001647
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID14841175
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available