Record Information
Version1.0
Creation date2010-04-08 22:06:26 UTC
Update date2019-11-26 03:00:18 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
ZangradoMeSH
Polyhydroxyflavan-3-olMeSH
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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, Positivesplash10-0006-0114590000-7fd73466ae61d7b32ff82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0446920000-e90bb0a2e1c1e3714cb42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-0591110000-df08b8a7f2f9b441aeaf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0101190000-b31c9c0fca7d80ef20c32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00e9-0914230000-a4c705979f1d6fc67fa92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1910000000-b98ec34dc51f844147092016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0010190000-1a235a0283d9b9f0a78e2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0214940000-42cf8f12882748e6f4f92021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ktf-0901480000-9a31aa132b216973a0a52021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000090000-dfcbeb46abd0824fb3bc2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-0130390000-4369984b9fad807701a32021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00c9-1916640000-0346683242ed543fd1422021-10-21View Spectrum
NMRNot Available
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 An agent that promotes hair growth and prevents hair loss, commonly used to treat alopecia and other hair-related disorders, by inhibiting dihydrotestosterone (DHT) and stimulating hair follicle growth.DUKE
Anti-atherosclerotic38070 An agent that prevents or slows the formation of atherosclerosis, a condition characterized by plaque buildup in arteries. It reduces inflammation, improves lipid profiles, and inhibits platelet aggregation, commonly used to manage cardiovascular diseases, such as coronary artery disease, and prevent heart attacks and strokes.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
Anti CVIAn antibiotic that counteracts colicin V, a protein involved in E. coli immunity, used to combat bacterial infections and potentially applied in treating E. coli-related diseases.DUKE
Anti-diabetic52217 An agent that regulates blood sugar levels, enhancing insulin sensitivity or secretion. Therapeutically, it's used to manage diabetes, reducing symptoms and complications, and commonly prescribed to treat type 1 and 2 diabetes, as well as gestational diabetes.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 histaminic37956 An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.DUKE
Anti-ischemic52217 An agent that reduces or prevents tissue damage from inadequate blood flow, commonly used to manage angina, heart attacks, and strokes by improving oxygen delivery and reducing cardiac workload.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti periodontalAn agent that prevents or treats gum disease, reducing inflammation and infection in the gums and supporting tissues of the teeth, commonly used in managing periodontitis and promoting oral health.DUKE
Anti-plaqueAn agent that removes or prevents the formation of dental plaque, a biofilm of bacteria, to prevent tooth decay and gum disease, commonly used in oral care products and therapeutic applications for periodontal health.DUKE
Anti proliferantAn agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.DUKE
Anti retinopathic52217 An agent that prevents or treats retinopathy, a disease damaging the retina. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing diabetic retinopathy and other retinal disorders, with key medical uses including preserving vision and preventing blindness.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
Anti-stroke52217 An agent that prevents or reduces the severity of stroke, typically by inhibiting blood clot formation or improving cerebral blood flow, commonly used in managing cardiovascular diseases, preventing stroke recurrence, and reducing stroke-related brain damage.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.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
Beta-glucuronidase inhibitor23924 An agent that blocks the activity of beta-glucuronidase, an enzyme that breaks down glucuronides. It reduces the toxicity of certain drugs and is used to manage conditions like cancer, inflammatory bowel disease, and irinotecan-induced diarrhea, improving treatment outcomes and reducing side effects.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
Cardioprotective38070 An agent that protects the heart from damage, reducing the risk of cardiovascular disease. It plays a biological role in mitigating cardiac stress and injury, with therapeutic applications in preventing heart attacks, strokes, and arrhythmias, and key medical uses in treating hypertension, heart failure, and coronary artery disease.DUKE
Collagenase inhibitor23924 An agent that blocks the activity of collagenase, an enzyme that breaks down collagen. It reduces tissue damage and inflammation, commonly used in managing conditions such as osteoarthritis, tendonitis, and wound healing.DUKE
CollagenicAn agent that stimulates collagen production, the primary protein in connective tissue, promoting tissue repair and regeneration. It has therapeutic applications in wound healing, orthopedics, and dermatology, with key medical uses including skin rejuvenation, joint health, and bone fracture repair.DUKE
DeodorantA substance that removes or conceals unpleasant smells, especially bodily odors, playing a hygienic role in reducing sweat-induced bacteria growth, with therapeutic applications in managing body odor disorders, and key medical uses in treating hyperhidrosis and bromhidrosis.DUKE
Elastase inhibitor23924 An agent that blocks the activity of elastase, an enzyme that breaks down elastin, reducing tissue damage and inflammation. Therapeutically, it's used to manage conditions like chronic obstructive pulmonary disease (COPD), cystic fibrosis, and emphysema, protecting lung tissue and improving respiratory function.DUKE
Gram(+)icide33282 An agent that targets and kills Gram-positive bacteria, playing a crucial role in treating bacterial infections. Therapeutically, it is used to combat infections caused by Gram-positive microorganisms, with key medical applications including treating skin infections, pneumonia, and sepsis.DUKE
Gram(-)icide33282 An agent that kills Gram-negative bacteria, playing a crucial role in treating infections. Therapeutically, it is used to combat bacterial infections, particularly those resistant to other antibiotics. Key medical uses include treating sepsis, pneumonia, and urinary tract infections caused by Gram-negative bacteria.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.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
Hypoglycemic35526 An agent that lowers blood glucose levels, playing a crucial role in glucose metabolism. Therapeutically, it is used to manage diabetes and insulin resistance, with key medical applications in treating type 1 and 2 diabetes, and preventing diabetic complications.DUKE
Ornithine-decarboxylase inhibitor23924 An agent that blocks the activity of ornithine decarboxylase, an enzyme involved in cell growth and proliferation. It reduces polyamine synthesis, inhibiting tumor growth and proliferation. Therapeutically, it is used to treat cancer, particularly in combination with other therapies, and has potential applications in managing parasitic infections and skin disorders.DUKE
Tyrosine kinase inhibitorAn agent that blocks the enzymatic activity of tyrosine kinases, enzymes responsible for the activation of many proteins involved in signal transduction pathways regulating cell growth and survival. Therapeutically, tyrosine kinase inhibitors are widely used in the treatment of various cancers and proliferative diseases, by halting aberrant signaling that drives tumor progression and pathological tissue remodeling.DUKE
Vasodilator35620 An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.DUKE
VasorelaxantAn agent that promotes vasorelaxation, reducing vascular tension and blood pressure. It plays a biological role in regulating blood flow and is therapeutically used to treat hypertension, angina, and heart failure, improving cardiovascular health.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).