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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:40:25 UTC
Update Date2019-07-23 06:26:26 UTC
HMDB IDHMDB0038369
Secondary Accession Numbers
  • HMDB38369
Metabolite Identification
Common NameProcyanidin B8
DescriptionProcyanidin B8 belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Procyanidin B8 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Procyanidin B8 has been detected, but not quantified in, several different foods, such as acorns, common grapes, fruits, lingonberries, and red raspberries. This could make procyanidin B8 a potential biomarker for the consumption of these foods.
Structure
Data?1563863185
Synonyms
ValueSource
Catechin(4a->6) epicatechinHMDB
Catechin-(4alpha->6)-epicatechinHMDB
Chemical FormulaC30H26O12
Average Molecular Weight578.5202
Monoisotopic Molecular Weight578.142426296
IUPAC Name(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-4-[(3R,4R)-3-(3,4-dihydroxyphenyl)-4,6,8-trihydroxy-3,4-dihydro-1H-2-benzopyran-7-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Name(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-4-[(3R,4R)-3-(3,4-dihydroxyphenyl)-4,6,8-trihydroxy-3,4-dihydro-1H-2-benzopyran-7-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
CAS Registry Number12798-60-6
SMILES
O[C@@H]1[C@H](OC2=CC(O)=CC(O)=C2[C@H]1C1=C(O)C2=C(C=C1O)[C@@H](O)[C@H](OC2)C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C30H26O12/c31-13-7-20(36)23-22(8-13)42-30(12-2-4-17(33)19(35)6-12)28(40)25(23)24-21(37)9-14-15(26(24)38)10-41-29(27(14)39)11-1-3-16(32)18(34)5-11/h1-9,25,27-40H,10H2/t25-,27+,28-,29+,30+/m0/s1
InChI KeyOHIUVDQGXUITJQ-VDKDFJRPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechins
Alternative Parents
Substituents
  • Catechin
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Chromane
  • Benzopyran
  • Isochromane
  • 1-benzopyran
  • 2-benzopyran
  • Catechol
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Dialkyl ether
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP2.22ALOGPS
logP2.86ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.55ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area220.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity146.86 m³·mol⁻¹ChemAxon
Polarizability58.07 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, Positivesplash10-03fs-0200950000-f7f8656081f7d8b8a051Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-007a-5200649000-ea02c51ab91db5fa91c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0510490000-618a58e1555c994ba2c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0523920000-7550fbfdfea13949250fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007c-0951310000-c8c812f6dbbb794b64ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0210190000-a01aeb153cf7b1c3fce7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0790660000-71360d7a941dba5bbd2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0920000000-37a980a0c4be22b9ec62Spectrum
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 IDNot Available
FooDB IDFDB017709
KNApSAcK IDC00009073
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProcyanidin B8
METLIN IDNot Available
PubChem Compound131752346
PDB IDNot Available
ChEBI IDNot Available
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.. .