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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:54:54 UTC
Update Date2019-07-23 06:24:29 UTC
HMDB IDHMDB0037661
Secondary Accession Numbers
  • HMDB37661
Metabolite Identification
Common 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). Outside of the human body, 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. A proanthocyanidin isolated from Cinnamomum cassia.
Structure
Data?1563863069
Synonyms
ValueSource
Cinnamtannin IHMDB
Epicatechin tetramerHMDB
[Epicatechin(4b->8)]3-epicatechinHMDB
Chemical FormulaC60H50O24
Average Molecular Weight1155.036
Monoisotopic Molecular Weight1154.26920249
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
Traditional 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
CAS Registry Number86631-38-1
SMILES
O[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
InChI Identifier
InChI=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
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
  • C-type proanthocyanidin
  • B-type proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Proanthocyanidin
  • Catechin
  • Flavan-3-ol
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • Flavan
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Catechol
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-6900000006-fd839ac63a319cc8efa0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-6400000089-09286542987f4ff0231cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-4200000079-5ee48e0f30fd3e52a245Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-a8d9260315c5ff39bf5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-6940210200-df945f1846b3c09225f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-2890310103-c627b3115f6da73073d3Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID196
FooDB IDFDB016784
KNApSAcK IDC00009107
Chemspider ID10272879
KEGG Compound IDC17625
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16130899
PDB IDNot Available
ChEBI ID81227
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .