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Showing Compound Procyanidin (FDB007223)

Record Information
Version1.0
Creation date2010-04-08 22:07:30 UTC
Update date2019-11-26 03:01:33 UTC
Primary IDFDB007223
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProcyanidin
DescriptionProcyanidin, also known as epicatechin-4alpha,8-epicatechin, is a member of the class of compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Procyanidin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Procyanidin can be found in cloves, ginkgo nuts, and soursop, which makes procyanidin a potential biomarker for the consumption of these food products. Procyanidins are members of the proanthocyanidin (or condensed tannins) class of flavonoids. They are oligomeric compounds, formed from catechin and epicatechin molecules. They yield cyanidin when depolymerized under oxidative conditions .
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Procyanidin, (2R-(2alpha,3alpha,4alpha(2'r*,3's*)))-isomerMeSH
Procyanidin, (2R-(2alpha,3beta,4beta(2R*,3R*)))-isomerMeSH
ProcyanidineMeSH
Procyanidin type aMeSH
Type a procyanidinMeSH
a-Type procyanidinMeSH
Epicatechin-4alpha,8-epicatechinMeSH
Procyanidinsmanual
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP2.27ALOGPS
logP3.64ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)8.64ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area229.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity147.16 m³·mol⁻¹ChemAxon
Polarizability57.25 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC30H26O13
IUPAC name2-(3,4-dihydroxyphenyl)-2-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
InChI IdentifierInChI=1S/C30H26O13/c31-14-7-19(35)16-11-25(28(41-23(16)9-14)12-1-3-17(33)20(36)5-12)43-30(13-2-4-18(34)21(37)6-13)29(40)27(39)26-22(38)8-15(32)10-24(26)42-30/h1-10,25,27-29,31-40H,11H2
InChI KeyHGVVOUNEGQIPMS-UHFFFAOYSA-N
Isomeric SMILESOC1C(O)C(OC2CC3=C(O)C=C(O)C=C3OC2C2=CC=C(O)C(O)=C2)(OC2=CC(O)=CC(O)=C12)C1=CC=C(O)C(O)=C1
Average Molecular Weight594.525
Monoisotopic Molecular Weight594.137340897
Classification
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
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Benzylether
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Ketal
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-diol
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0920040000-c07bb71808a61065f068Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0920010000-17bd24728bbdffe1632cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-1900000000-8ab82ba428b11d1aa9cbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-0902150000-465c6cb31c9b84ec5e32Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0819130000-a39f3d60a8de6d386c83Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-1900000000-bc44a7753a7cbc8d61cfSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDPROCYANIDIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
antibiotic22582 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti edemicDUKE
anti exudativeDUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
capillariprotectiveDUKE
hyaluronidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).