Record Information
Version1.0
Creation date2010-04-08 22:12:39 UTC
Update date2019-11-27 17:32:11 UTC
Primary IDFDB016784
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCinnamtannin A2
DescriptionCinnamtannin A2 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''. Cinnamtannin A2 is an extremely weak basic (essentially neutral) compound (based on its pKa). Cinnamtannin A2 is found, on average, in the highest concentration in chocolates and cocoa powders. Cinnamtannin A2 has also been detected, but not quantified in, a few different foods, such as chinese cinnamons, cocoa beans, and herbs and spices. This could make cinnamtannin A2 a potential biomarker for the consumption of these foods.
CAS Number86631-38-1
Structure
Thumb
Synonyms
SynonymSource
Cinnamtannin IHMDB
Epicatechin tetramerHMDB
[Epicatechin(4b->8)]3-epicatechinHMDB
[Epicatechin(4b->8)]3epicatechindb_source
Cinnamtannin A2manual
Predicted Properties
PropertyValueSource
Water Solubility0.58 g/LALOGPS
logP4.05ALOGPS
logP5.76ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.61ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count20ChemAxon
Polar Surface Area441.52 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity291.52 m³·mol⁻¹ChemAxon
Polarizability115.38 ųChemAxon
Number of Rings12ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC60H50O24
IUPAC name(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
InChI IdentifierInChI=1S/C60H50O24/c61-23-13-34(71)42-41(14-23)81-55(20-2-6-26(63)31(68)10-20)51(78)48(42)44-36(73)17-38(75)46-50(53(80)57(83-59(44)46)22-4-8-28(65)33(70)12-22)47-39(76)18-37(74)45-49(52(79)56(84-60(45)47)21-3-7-27(64)32(69)11-21)43-35(72)16-29(66)24-15-40(77)54(82-58(24)43)19-1-5-25(62)30(67)9-19/h1-14,16-18,40,48-57,61-80H,15H2/t40-,48-,49+,50-,51-,52-,53-,54-,55-,56-,57-/m1/s1
InChI KeyQFLMUASKTWGRQE-JNIIMKSASA-N
Isomeric SMILESO[C@@H]1CC2=C(O)C=C(O)C([C@@H]3[C@@H](O)[C@H](OC4=C([C@@H]5[C@@H](O)[C@H](OC6=C([C@@H]7[C@@H](O)[C@H](OC8=CC(O)=CC(O)=C78)C7=CC=C(O)C(O)=C7)C(O)=CC(O)=C56)C5=CC=C(O)C(O)=C5)C(O)=CC(O)=C34)C3=CC=C(O)C(O)=C3)=C2O[C@@H]1C1=CC=C(O)C(O)=C1
Average Molecular Weight1155.036
Monoisotopic Molecular Weight1154.26920249
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 62.39%; H 4.36%; O 33.24%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]D +89.2 (c, 0.9 in Me2CO)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-6900000006-fd839ac63a319cc8efa0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-6400000089-09286542987f4ff0231cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-4200000079-5ee48e0f30fd3e52a245View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-a8d9260315c5ff39bf5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-6940210200-df945f1846b3c09225f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-2890310103-c627b3115f6da73073d3View in MoNA
ChemSpider ID10272879
ChEMBL IDNot Available
KEGG Compound IDC17625
Pubchem Compound ID16130899
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID196
DrugBank IDNot Available
HMDB IDHMDB37661
CRC / DFC (Dictionary of Food Compounds) IDKTF90-G:KTF91-H
EAFUS IDNot Available
Dr. Duke IDCINNAMTANNIN-A1|CINNAMTANNIN-A2
BIGG IDNot Available
KNApSAcK IDC00009107
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— 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.