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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:44:52 UTC
Update Date2019-07-23 06:14:49 UTC
HMDB IDHMDB0033974
Secondary Accession Numbers
  • HMDB33974
Metabolite Identification
Common NameProcyanidin B3
DescriptionProcyanidin B3, also known as C-(4a,8)-C, 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''. Thus, procyanidin B3 is considered to be a flavonoid lipid molecule. Procyanidin B3 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Procyanidin B3 is found, on average, in the highest concentration within a few different foods, such as quinces, barley, and broad beans and in a lower concentration in sweet cherries, yellow wax beans, and apples. Procyanidin B3 has also been detected, but not quantified in, several different foods, such as guava, carrots, apple ciders, millets, and common wheats. This could make procyanidin B3 a potential biomarker for the consumption of these foods. A proanthocyanidin consisting of two molecules of (+)-catechin joined by a bond between positions 4 and 8' in alpha-configuration.
Structure
Data?1563862489
Synonyms
ValueSource
C-(4a,8)-CChEBI
Catechin(4a->8)catechinChEBI
Catechin-(4alpha->8)-catechinChEBI
Proanthocyanidin b3ChEBI
Catechin-(4a->8)-catechinGenerator
Catechin-(4α->8)-catechinGenerator
2,3-trans-ProanthocyanidinHMDB
Afzelechin-(4alpha->8)-afzelechinHMDB
Procyanidin b-3HMDB
Chemical FormulaC30H26O12
Average Molecular Weight578.526
Monoisotopic Molecular Weight578.142426277
IUPAC Name(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Nameprocyanidin B3
CAS Registry Number23567-23-9
SMILES
[H][C@@]1([C@H](O)[C@H](OC2=CC(O)=CC(O)=C12)C1=CC(O)=C(O)C=C1)C1=C(O)C=C(O)C2=C1O[C@@H]([C@@H](O)C2)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28+,29+/m0/s1
InChI KeyXFZJEEAOWLFHDH-AVFWISQGSA-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
  • 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:

Source:

Biological location:

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 Solubility0.14 g/LALOGPS
logP2.29ALOGPS
logP3.12ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.69ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area220.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity146.51 m³·mol⁻¹ChemAxon
Polarizability57.27 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9400124000-0e1dd79d9ddf757d4df7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03mj-0500790000-0d28ce5601f00c17eaa5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0110980000-5100aeb456b72604bfbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0334920000-f9222e1bae7f0bca6417Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0076-0491110000-c8af712677eef1677727Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000290000-ae7911e8a6b7e2e8867eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kbr-0920440000-53d4ef58d673c17bbbb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0910000000-851c43689a6c620aa704Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 ID152
FooDB IDFDB012205
KNApSAcK IDC00009071
Chemspider ID129476
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProcyanidin_B3
METLIN IDNot Available
PubChem Compound146798
PDB IDNot Available
ChEBI ID75630
Food Biomarker OntologyNot Available
VMH IDNot Available
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.. .