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Showing Compound Epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-galactoside (FDB000126)

Record Information
Version1.0
Creation date2010-04-08 22:04:27 UTC
Update date2019-11-26 02:54:32 UTC
Primary IDFDB000126
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEpicatechin-(2alpha->7,4alpha->8)-epicatechin 3-galactoside
DescriptionEpicatechin-(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''. Epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-galactoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-galactoside can be found in chocolate and cocoa powder, which makes epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-galactoside a potential biomarker for the consumption of these food products.
CAS Number490-46-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Epicatechin-(2a->7,4a->8)-epicatechin 3-galactosideGenerator
Epicatechin-(2α->7,4α->8)-epicatechin 3-galactosideGenerator
(-)-Epicatechin-(2a-7)(4a-8)-epicatechin 3-O-galactosidedb_source
3T-O-beta-D-Galactopyranosyl-ent-(-)-Epicatechin-(2alpha->7, 4alpha->8)-(-)-Epicatechinmanual
Epicatechin-(2alpha->7,4alpha->8)-epicatechin 3-galactosidemanual
Predicted Properties
PropertyValueSource
Water Solubility0.26 g/LALOGPS
logP2.41ALOGPS
logP3.2ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.71ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area248.45 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity173.27 m³·mol⁻¹ChemAxon
Polarizability68.61 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC36H34O15
IUPAC name(2R,3R,4S,5R,6R)-2-{[(1R,5S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-17,19-dihydroxy-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaen-21-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
InChI IdentifierInChI=1S/C36H34O15/c37-13-26-30(44)31(45)32(46)35(48-26)49-34-29-27-22(43)11-17(38)12-25(27)51-36(34,16-4-6-19(40)21(42)10-16)50-24-8-3-14-2-7-23(47-33(14)28(24)29)15-1-5-18(39)20(41)9-15/h1,3-6,8-12,23,26,29-32,34-35,37-46H,2,7,13H2/t23-,26+,29+,30-,31-,32+,34+,35+,36+/m0/s1
InChI KeyMVLCXMXCRQYNIC-TWULTLMFSA-N
Isomeric SMILESOC[C@H]1O[C@H](O[C@@H]2[C@@H]3C4=C(O[C@]2(OC2=C3C3=C(CC[C@H](O3)C3=CC(O)=C(O)C=C3)C=C2)C2=CC(O)=C(O)C=C2)C=C(O)C=C4O)[C@H](O)[C@@H](O)[C@H]1O
Average Molecular Weight706.6462
Monoisotopic Molecular Weight706.189770418
Classification
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
  • Bi- and polyflavonoid skeleton
  • Catechin
  • Pyranoflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavan-3-ol
  • Hydroxyflavonoid
  • Flavan
  • Pyranochromene
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Phenol
  • Ketal
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Acetal
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052k-0300092300-b65c76758ee7673303e52016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mk-0400591000-47c65f5b8211c61ad5a72016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1901521000-79a35b0c5198f2a7f6a02016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-2420083900-20389803443873a4229b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-1410191000-9a7916d635d39f958b342016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0553-6790150000-8f47f8770dc1d570f8682016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4j-0000181900-8698603040661b8e7b1b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-0000029200-6257e691d83f4c26608d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-9300668100-773d944f9bdba199ecfb2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000001900-d11f0b5c05bb811c1d0b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2200039700-e99869259575731c256f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6310590000-72e55eb34069bfed27a32021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID195
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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 Reference
  1. Natsume M, Osakabe N, Yamagishi M, Takizawa T, Nakamura T, Miyatake H, Hatano T, Yoshida T: Analyses of polyphenols in cacao liquor, cocoa, and chocolate by normal-phase and reversed-phase HPLC. Biosci Biotechnol Biochem. 2000 Dec;64(12):2581-7. Pubmed [Structure]
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.