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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:44:48 UTC
Update Date2020-11-09 23:29:42 UTC
HMDB IDHMDB0033973
Secondary Accession Numbers
  • HMDB33973
Metabolite Identification
Common NameProcyanidin B2
DescriptionProcyanidin B2, also known as procyanidol B2 or ec-(4b,8)-ec, 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 B2 is considered to be a flavonoid lipid molecule. Procyanidin B2 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Procyanidin B2 is found, on average, in the highest concentration within a few different foods, such as cocoa powders, chocolates, and broad beans and in a lower concentration in hot chocolates, quinces, and rubus (blackberry, raspberry). Procyanidin B2 has also been detected, but not quantified in, several different foods, such as apple ciders, wheats, sorghums, loquats, and rices. This could make procyanidin B2 a potential biomarker for the consumption of these foods.
Structure
Data?1563862489
Synonyms
ValueSource
EC-(4b,8)-ecChEBI
Epicathechin-(4beta->8)-epicathechinChEBI
Proanthocyanidin b2ChEBI
Procyanidol b2ChEBI
Epicathechin-(4b->8)-epicathechinGenerator
Epicathechin-(4β->8)-epicathechinGenerator
(+)-Procyanidin b2HMDB
2,3-cis-ProanthocyanidinHMDB
cis,Cis"-4,8"-bi(3,3',4',5,7-pentahydroxyflavane)HMDB
Procyanidin dimer b2HMDB
Chemical FormulaC30H26O12
Average Molecular Weight578.526
Monoisotopic Molecular Weight578.142426277
IUPAC Name(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-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 B2
CAS Registry Number29106-49-8
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-/m1/s1
InChI KeyXFZJEEAOWLFHDH-NFJBMHMQSA-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
Polarizability57.15 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 (Non-derivatized) - 70eV, Positivesplash10-03mj-0500790000-0d28ce5601f00c17eaa5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9400124000-e693e1a36e8e5fdd34e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0551-0790100000-ba210c828673adbc07c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0300090000-f0366f761dd35900f408Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0000190000-82899b68a12b3ff7f0a3Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0050950000-7c3e401e0cdbb5a2fabaSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-052r-0191600000-9a516f7211ac18d6e0feSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-052r-0191600000-9a516f7211ac18d6e0feSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0551-0790100000-ba210c828673adbc07c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0300090000-f0366f761dd35900f408Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0000190000-82899b68a12b3ff7f0a3Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0050950000-7c3e401e0cdbb5a2fabaSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-052r-0191600000-9a516f7211ac18d6e0feSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-052r-0391200000-f0bdc661ae52358a3a75Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-002u-0290300000-42d1534f346f0b46137eSpectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0ika-0019605000-2910ce23bfd62dd5d6b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0550-0291810000-cae7840ddc5a7ce6e9c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0970640000-534c1d685846bd293495Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0551-0790100000-ba210c828673adbc07c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0000190000-82899b68a12b3ff7f0a3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0050950000-7c3e401e0cdbb5a2fabaSpectrum
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 Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 151 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 151 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID151
FooDB IDFDB012204
KNApSAcK IDC00009077
Chemspider ID109417
KEGG Compound IDC17639
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProcyanidin_B2
METLIN IDNot Available
PubChem Compound122738
PDB IDNot Available
ChEBI ID75632
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.. .