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Showing Compound Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-epicatechin (FDB016799)

Record Information
Version1.0
Creation date2010-04-08 22:12:39 UTC
Update date2019-11-26 03:13:49 UTC
Primary IDFDB016799
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEpicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-epicatechin
DescriptionEpicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-epicatechin, also known as cinnamtannin b-1, 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''. Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-epicatechin is an extremely weak basic (essentially neutral) compound (based on its pKa). Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-epicatechin has been detected, but not quantified in, several different foods, such as ceylon cinnamons, fruits, herbs and spices, and lingonberries. This could make epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-epicatechin a potential biomarker for the consumption of these foods.
CAS Number88082-60-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
Cinnamtannin B1manual
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC45H36O18
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
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
Isomeric 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
Average Molecular Weight864.765
Monoisotopic Molecular Weight864.190164319
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 62.50%; H 4.20%; O 33.30%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +70.3 (c, 1.1 in Me2CO)DFC
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, Positivesplash10-0292-0300013490-ec26e82ac3cbfe2e2b342016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r7-0601093740-7b261c7017bedecadbca2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0903020120-941235b046ebe1534e232016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0100010290-e775ab4962207ca269ce2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gw1-0940220440-743d2b7bb64c3c3212792016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vr-0962322000-e8fd77cb8ef30e20331b2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-8dd342560dbe7ef6a1522021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000000390-134540ced36417c6563e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-1730000790-99e7da205ab13d512b512021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000190-9b689094479cf9a1a18d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0210100590-170e2f269eed5e69760a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-1710101960-7cfe213402c5bcdff38b2021-09-22View Spectrum
NMRNot Available
ChemSpider ID417255
ChEMBL IDNot Available
KEGG Compound IDC17631
Pubchem Compound ID475277
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID189
DrugBank IDNot Available
HMDB IDHMDB37672
CRC / DFC (Dictionary of Food Compounds) IDKTG74-J:KTG75-K
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00009291
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 ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.