Record Information
Version1.0
Creation date2010-04-08 22:06:26 UTC
Update date2018-05-28 23:14:15 UTC
Primary IDFDB004901
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProanthocyanidins
DescriptionProanthocyanidins, also known as zangrado or polyhydroxyflavan-3-ol, is a member of the class of compounds known as biflavonoids and polyflavonoids. Biflavonoids and polyflavonoids 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''. Proanthocyanidins is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Proanthocyanidins can be found in a number of food items such as roselle, allspice, cocoa bean, and sweet bay, which makes proanthocyanidins a potential biomarker for the consumption of these food products. Proanthocyanidins were discovered in 1947 by Jacques Masquelier, who developed and patented techniques for the extraction of oligomeric proanthocyanidins from pine bark and grape seeds. Often associated with consumer products made from cranberries, grape seeds or red wine, proanthocyanidins were once proposed as factors inhibiting urinary tract infections in women, but this research has been refuted by expert scientific committees .
CAS Number18206-61-6
Structure
Thumb
Synonyms
SynonymSource
Polyhydroxyflavan-3-olMeSH
ZangradoMeSH
ProanthocyanidinsMeSH
Polymers, anthocyanidinMeSH
ProcyanidinsMeSH
Anthocyanidin polymersMeSH
Condensed tanninMeSH
Condensed tanninsMeSH
Tannin, condensedMeSH
Tannins, condensedMeSH
ProanthocyanidinMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.094 g/LALOGPS
logP2.42ALOGPS
logP3.26ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.86ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area209.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity150.99 m³·mol⁻¹ChemAxon
Polarizability58.52 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC31H28O12
IUPAC name(2R,3R,4R)-4-[(3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
InChI IdentifierInChI=1S/C31H28O12/c1-41-31-20(37)6-13(7-21(31)38)28-22(39)10-16-17(34)11-19(36)25(30(16)43-28)26-24-18(35)8-15(33)9-23(24)42-29(27(26)40)12-2-4-14(32)5-3-12/h2-9,11,22,26-29,32-40H,10H2,1H3/t22-,26-,27-,28?,29-/m1/s1
InChI KeyJPFCOVZKLAXXOE-XBNSMERZSA-N
Isomeric SMILES[H][C@@]1(O)CC2=C(OC1([H])C1=CC(O)=C(OC)C(O)=C1)C(=C(O)C=C2O)[C@@]1([H])C2=C(O)C=C(O)C=C2O[C@]([H])(C2=CC=C(O)C=C2)[C@]1([H])O
Average Molecular Weight592.553
Monoisotopic Molecular Weight592.158076342
Classification
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
  • Epigallocatechin
  • Catechin
  • 4p-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavan-3-ol
  • Hydroxyflavonoid
  • Flavan
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Methoxyphenol
  • Resorcinol
  • Phenol ether
  • Anisole
  • Phenoxy compound
  • Methoxybenzene
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen 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
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0114590000-7fd73466ae61d7b32ff8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0446920000-e90bb0a2e1c1e3714cb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-0591110000-df08b8a7f2f9b441aeafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0101190000-b31c9c0fca7d80ef20c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00e9-0914230000-a4c705979f1d6fc67fa9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1910000000-b98ec34dc51f84414709View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID26267
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDPROANTHOCYANIDINS|PROANTHOCYANIDIN
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 IDProanthocyanidin
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 alopecic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti atherosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti CVIDUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti edemicDUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti ischemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti periodontalDUKE
anti plaqueDUKE
anti proliferantDUKE
anti retinopathic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti stroke52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
beta-glucuronidase 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
capillariprotectiveDUKE
cardioprotective38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
collagenase 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
collagenicDUKE
deodorantDUKE
elastase 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
Gram(+)icide33282 A substance that kills or slows the growth of bacteria.DUKE
Gram(-)icide33282 A substance that kills or slows the growth of bacteria.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
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
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
ornithine-decarboxylase 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
propecicDUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
vasorelaxantDUKE
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).