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
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
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-c07bb71808a61065f0682016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0920010000-17bd24728bbdffe1632c2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-1900000000-8ab82ba428b11d1aa9cb2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-0902150000-465c6cb31c9b84ec5e322016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0819130000-a39f3d60a8de6d386c832016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-1900000000-bc44a7753a7cbc8d61cf2016-08-03View Spectrum
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 An agent that reduces or blocks allergic reactions, commonly used to manage symptoms of allergies, such as itching, sneezing, and inflammation, by inhibiting the release of histamine and other chemical mediators, providing relief in conditions like hay fever, asthma, and skin allergies.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Antibiotic22582 An agent that inhibits the growth of or destroys microorganisms, particularly bacteria. Therapeutically, antibiotics are used to treat bacterial infections, such as pneumonia, tuberculosis, and skin infections, by targeting specific biochemical processes essential for microbial survival.DUKE
Anti-edemicAn agent that relieves or prevents edema, reducing abnormal fluid accumulation in tissues or the circulatory system, commonly used to treat conditions such as swelling, inflammation, and water retention.DUKE
Anti exudativeAn agent that reduces fluid or material leakage from cells and tissues, often caused by inflammation or injury, promoting healing and tissue repair, with therapeutic applications in managing edema, wounds, and inflammatory conditions.DUKE
Anti HIV22587 An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
CapillariprotectiveAn agent that protects and strengthens capillaries, alleviating conditions such as fragility and permeability. Therapeutically, it helps manage disorders like hemorrhoids and varicose veins, and has applications in reducing inflammation and improving microcirculation, commonly used in vascular health and wound healing.DUKE
Hyaluronidase inhibitor23924 An agent that blocks the activity of hyaluronidase, an enzyme that breaks down hyaluronic acid. This inhibition helps maintain hyaluronic acid levels, reducing inflammation and improving tissue hydration, with therapeutic applications in ophthalmology, dermatology, and oncology, and key medical uses in treating dry eye, wrinkles, and certain cancers.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Xanthine oxidase inhibitor35634 An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function.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).