Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-epicatechin (CHEM031179)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:27:09 UTC
Update Date2016-11-09 01:19:13 UTC
Accession NumberCHEM031179
Identification
Common NameEpicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-epicatechin
ClassSmall Molecule
DescriptionIsolated from cinnamon bark (Cinnamomum zeylanicum) and from cowberry (Vaccinium vitis-idaea). Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-epicatechin is found in many foods, some of which are fruits, herbs and spices, ceylon cinnamon, and lingonberry.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Epicatechin-(2b->7,4b->8)-epicatechin-(4b->8)-epicatechinGenerator
Epicatechin-(2β->7,4β->8)-epicatechin-(4β->8)-epicatechinGenerator
Cinnamtannin b1HMDB
Epicatechin(2b->7,4b->8)epicatechin(4b->8)epicatechinHMDB
Cinnamtannin b-1HMDB
Cinnamtannin D-1HMDB
Chemical FormulaC45H36O18
Average Molecular Mass864.765 g/mol
Monoisotopic Mass864.190 g/mol
CAS Registry Number88082-60-4
IUPAC Name(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol
Traditional Name(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol
SMILES[H][C@@]12[C@@H](O)[C@@](OC3=CC(O)=CC(O)=C13)(OC1=C2C2=C([C@@H]([C@@H](O)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C=C(O)C3=C2O[C@@H]([C@H](O)C3)C2=CC=C(O)C(O)=C2)C(O)=C1)C1=CC=C(O)C(O)=C1
InChI IdentifierInChI=1S/C45H36O18/c46-18-10-27(54)33-31(11-18)62-45(17-3-6-22(49)26(53)9-17)44(59)38(33)36-32(63-45)14-29(56)35-37(39(58)41(61-43(35)36)16-2-5-21(48)25(52)8-16)34-28(55)13-23(50)19-12-30(57)40(60-42(19)34)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+/m1/s1
InChI KeyBYSRPHRKESMCPO-LQNPQWRQSA-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 ParentsNot Available
SubstituentsNot Available
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)8.6ChemAxon
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
Polarizability85.24 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, Positivesplash10-0292-0300013490-ec26e82ac3cbfe2e2b34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r7-0601093740-7b261c7017bedecadbcaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0903020120-941235b046ebe1534e23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0100010290-e775ab4962207ca269ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gw1-0940220440-743d2b7bb64c3c321279Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vr-0962322000-e8fd77cb8ef30e20331bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-8dd342560dbe7ef6a152Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000000390-134540ced36417c6563eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-1730000790-99e7da205ab13d512b51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000190-9b689094479cf9a1a18dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0210100590-170e2f269eed5e69760aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-1710101960-7cfe213402c5bcdff38bSpectrum
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 IDHMDB0037672
FooDB IDFDB016799
Phenol Explorer IDNot Available
KNApSAcK IDC00009291
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID417255
ChEBI ID69304
PubChem Compound ID475277
Kegg Compound IDC17631
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.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21875098