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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:54:21 UTC
Update Date2019-07-23 06:24:27 UTC
HMDB IDHMDB0037655
Secondary Accession Numbers
  • HMDB37655
Metabolite Identification
Common NameProanthocyanidin A2
DescriptionProanthocyanidin A2, also known as ec-(4b,8)(2b,7)-ec or procyanidin 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''. Proanthocyanidin A2 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, proanthocyanidin A2 has been detected, but not quantified in, several different foods, such as chinese cinnamons, herbs and spices, lingonberries, cinnamons, and ceylon cinnamons. This could make proanthocyanidin A2 a potential biomarker for the consumption of these foods. A proanthocyanidin obtained by the condensation of (-)-epicatechin units.
Structure
Data?1563863067
Synonyms
ValueSource
Epicatechin-(2beta->7,4beta->8)-epicatechinChEBI
Epicatechin-(2b->7,4b->8)-epicatechinGenerator
Epicatechin-(2β->7,4β->8)-epicatechinGenerator
(+)-Proanthocyanidin a2HMDB
EC-(4b,8)(2b,7)-ecHMDB
Proanthocyanidin a-2HMDB
Procyanidin a2HMDB
Procyanidin dimer a2HMDB
ProcyanidoepicatechinHMDB
Procyanidol a2HMDB
Chemical FormulaC30H24O12
Average Molecular Weight576.51
Monoisotopic Molecular Weight576.126776213
IUPAC Name(1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol
Traditional Name(1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol
CAS Registry Number41743-41-3
SMILES
O[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C1=C(O[C@@]3(OC4=C([C@H]1[C@H]3O)C(O)=CC(O)=C4)C1=CC(O)=C(O)C=C1)C=C2O
InChI Identifier
InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26-,27-,29-,30+/m1/s1
InChI KeyNSEWTSAADLNHNH-LSBOWGMISA-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
  • A-type proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Proanthocyanidin
  • Catechin
  • Pyranoflavonoid
  • Flavan-3-ol
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • Flavan
  • Pyranochromene
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Catechol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Ketal
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Acetal
  • 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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.43ALOGPS
logP3.59ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.66ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area209.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity144.2 m³·mol⁻¹ChemAxon
Polarizability55.55 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-0502790000-304f891b1b3211f028e2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05d0-9501045000-a879ec29ba94548eeefcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0310690000-54ea277863ce3855e4f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0600930000-0793c36e7b827dadce6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900010000-eb8f4971f0158e4f45e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0110290000-ced82e7f8aa80a1b71adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pk9-0910470000-77ee610d048e0f3bfd15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-0910000000-d53675b4ba6a9383bc64Spectrum
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 IDNot Available
FooDB IDFDB016778
KNApSAcK IDC00002934
Chemspider IDNot Available
KEGG Compound IDC10237
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProanthocyanidin_A2
METLIN IDNot Available
PubChem Compound124025
PDB IDNot Available
ChEBI ID28472
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.. .