ent-Epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-galactoside (CHEM023897)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:21:26 UTC
Update Date2016-11-09 01:17:47 UTC
Accession NumberCHEM023897
Identification
Common Nameent-Epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-galactoside
ClassSmall Molecule
DescriptionEnt-epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-galactoside 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-galactoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Ent-epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-galactoside can be found in cocoa bean, which makes ent-epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-galactoside 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-galactosideGenerator
ent-Epicatechin-(2α->7,4α->8)-epicatechin 3-galactosideGenerator
Chemical FormulaC36H34O17
Average Molecular Mass738.645 g/mol
Monoisotopic Mass738.180 g/mol
CAS Registry Number135048-84-9
IUPAC Name(5R,6R,13R,21S)-5,13-bis(3,4-dihydroxyphenyl)-21-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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(5R,6R,13R,21S)-5,13-bis(3,4-dihydroxyphenyl)-21-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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
SMILESOC[C@H]1O[C@@H](O[C@H]2C3C4=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(O)=C(O)C=C2)C=C(O)C=C4O)[C@H](O)[C@@H](O)[C@H]1O
InChI IdentifierInChI=1S/C36H34O17/c37-11-25-29(46)30(47)31(48)35(49-25)51-34-28-26-21(44)7-14(38)8-23(26)52-36(34,13-2-4-17(40)20(43)6-13)53-24-10-18(41)15-9-22(45)32(50-33(15)27(24)28)12-1-3-16(39)19(42)5-12/h1-8,10,22,25,28-32,34-35,37-48H,9,11H2/t22-,25-,28?,29+,30+,31-,32-,34+,35+,36-/m1/s1
InChI KeyJUIIUJBWZYKSEP-QLBYNWDUSA-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
  • Proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Catechin
  • Pyranoflavonoid
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • Flavan-3-ol
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavan
  • Pyranochromene
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Phenol
  • Ketal
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Oxane
  • Monosaccharide
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Alcohol
  • 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 Solubility0.72 g/LALOGPS
logP1.62ALOGPS
logP1.82ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)8.66ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area288.91 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity176.61 m³·mol⁻¹ChemAxon
Polarizability70.5 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, Positivesplash10-05dr-0200190600-97706664d5aeea34bf2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0300590100-60d6fcf00696e0cd0675Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1912820100-f1a3b8bc2fd3ce81fbb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-1310061900-3c9fef71e9696d7e9849Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1800191200-389652470c629f0c6f66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-6961540000-20666cf2d2b17312d439Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-cd954687a724d5f6db73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1200033900-d9761220af502216e86eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3200391100-3d0325e3fe92991f806aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0000060900-5a501af86220764f2e74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00bj-0100029800-211026e199f9acf39a35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vr-7400339000-bd9c36330ebe2cce6eaeSpectrum
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 IDFDB001648
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 IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available