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Showing Compound Proanthocyanidin A2 (FDB016778)

Record Information
Version1.0
Creation date2010-04-08 22:12:38 UTC
Update date2025-11-19 01:49:43 UTC
Primary IDFDB016778
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProanthocyanidin A2
DescriptionProanthocyanidin A2 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''. Proanthocyanidin A2 is an extremely weak basic (essentially neutral) compound (based on its pKa). Proanthocyanidin A2 has been detected, but not quantified in, several different foods, such as herbs and spices, avocado, lingonberries, ceylon cinnamons, and apples. This could make proanthocyanidin A2 a potential biomarker for the consumption of these foods.
CAS Number41743-41-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(+)-Proanthocyanidin a2HMDB
EC-(4b,8)(2b,7)-ecHMDB
Epicatechin-(2b->7,4b->8)-epicatechinHMDB
Epicatechin-(2beta->7,4beta->8)-epicatechinHMDB
Proanthocyanidin a-2HMDB
Procyanidin a2HMDB
Procyanidin dimer a2HMDB
ProcyanidoepicatechinHMDB
Procyanidol a2HMDB
(+)-Proanthocyanidin A2biospider
EC-(4b,8)(2b,7)-ECdb_source
Proanthocyanidin A-2biospider
Proanthocyanidin A2db_source
Procyanidin A2db_source
Procyanidin dimer A2db_source
Procyanidol A2biospider
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.52ALOGPS
logP4.1ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.73ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area209.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity149.24 m³·mol⁻¹ChemAxon
Polarizability58.11 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC31H26O12
IUPAC name(1R,5R,6R,13S,21R)-13-(3,4-dihydroxy-5-methylphenyl)-5-(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol
InChI IdentifierInChI=1S/C31H26O12/c1-11-4-13(6-20(37)27(11)39)31-30(40)26(24-19(36)7-14(32)8-22(24)42-31)25-23(43-31)10-17(34)15-9-21(38)28(41-29(15)25)12-2-3-16(33)18(35)5-12/h2-8,10,21,26,28,30,32-40H,9H2,1H3/t21-,26-,28-,30-,31+/m1/s1
InChI KeyDWMJRBXZWVVPDB-UYVQOXPASA-N
Isomeric SMILESCC1=C(O)C(O)=CC(=C1)[C@@]12OC3=CC(O)=CC(O)=C3[C@@H]([C@H]1O)C1=C3O[C@@H]([C@H](O)CC3=C(O)C=C1O2)C1=CC=C(O)C(O)=C1
Average Molecular Weight590.5309
Monoisotopic Molecular Weight590.142426296
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
  • A-type proanthocyanidin
  • Proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Catechin
  • Pyranoflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavan
  • Pyranochromene
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • M-cresol
  • O-cresol
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Ketal
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Toluene
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Oxacycle
  • Ether
  • Acetal
  • Polyol
  • Organoheterocyclic compound
  • 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 CompositionC 62.50%; H 4.20%; O 33.30%DFC
Melting PointMp 300°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +64 (Me2CO)DFC
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, Positivesplash10-00dl-0900580000-b35a41d6dd7d0f94b9c62016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0900830000-605c12946bf657edebea2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-2900010000-662eef0e7f9ffc57f4bd2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0110290000-6e36ea0cc5dfe4653f5e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fe0-0900450000-e3f4fbc0903e73bb4d142016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-0910000000-b64582e6c380a5e9a1172016-08-03View Spectrum
NMRNot Available
ChemSpider ID30777195
ChEMBL IDNot Available
KEGG Compound IDC10237
Pubchem Compound ID124025
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID176
DrugBank IDNot Available
HMDB IDHMDB37655
CRC / DFC (Dictionary of Food Compounds) IDKTF42-T:KTF43-U
EAFUS IDNot Available
Dr. Duke IDPROANTHOCYANIDIN-A-2|PROCYANIDIN-A-2
BIGG IDNot Available
KNApSAcK IDC00002934
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 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 capillary-fragilityAn agent that strengthens capillary walls to prevent rupture, reducing bruising and bleeding. It plays a biological role in maintaining vascular integrity, and has therapeutic applications in treating conditions like purpura and hemorrhoids, with key medical uses in preventing and managing microvascular damage.DUKE
Anti elastase23924 An agent that inhibits elastase activity, reducing tissue damage and inflammation. It plays a biological role in protecting tissues from enzymatic degradation. Therapeutically, it is used to manage conditions such as chronic obstructive pulmonary disease (COPD), cystic fibrosis, and acute respiratory distress syndrome (ARDS), where excessive elastase activity contributes to disease progression.DUKE
Anti enzymaticAn agent that inhibits or counteracts enzyme activity, playing a crucial biological role in regulating metabolic pathways. Therapeutically, it has applications in managing enzyme-related disorders. Key medical uses include treating conditions like cancer, inflammatory diseases, and genetic disorders by blocking specific enzyme actions.DUKE
Anti erythemic50177 An agent that reduces redness of the skin, often used to treat conditions like rosacea and eczema. It plays a biological role in inhibiting inflammation and dilating blood vessels, and has therapeutic applications in dermatology, with key medical uses including topical creams and ointments to alleviate skin redness and irritation.DUKE
Anti glucuronidase23924 An enzyme inhibitor that blocks glucuronidase activity, preventing the breakdown of glucuronides. It has therapeutic applications in reducing beta-glucuronidase-mediated toxicity and is used to enhance cancer chemotherapy, particularly in treatments involving glucuronide-based prodrugs, and to manage certain gastrointestinal disorders.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.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 peroxidantAn agent that prevents oxygen atom and peroxide formation, reducing oxidative stress and cell damage. It plays a biological role in protecting cells from free radicals. Therapeutically, it's used to manage conditions like cancer, Alzheimer's, and atherosclerosis, with key medical applications in neuroprotection, cardiovascular health, and anti-aging.DUKE
Anti-proteolyticAn agent that prevents digestion of proteins, playing a biological role in protecting tissues from damage. Therapeutically, it's used to manage conditions like pancreatitis and ulcers, with key medical applications in reducing inflammation and promoting wound healing.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
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
Sunscreen52217 A topical agent that blocks UV radiation, preventing skin damage and reducing the risk of skin cancer. Its therapeutic applications include protection against sunburn, photoaging, and photodermatoses. Key medical uses include prevention of melanoma, basal cell carcinoma, and squamous cell carcinoma, as well as management of photosensitive disorders.DUKE
VenotonicAn agent that promotes venous drainage, enhancing blood flow and reducing venous pressure. It plays a biological role in improving circulation and is therapeutically applied to treat conditions like varicose veins, edema, and chronic venous insufficiency, reducing symptoms of swelling and pain.DUKE
Vulnerary73336 An agent that promotes wound healing, tissue repair, and skin regeneration. It facilitates the biological process of recovery, reducing inflammation and infection. Therapeutically, vulneraries are used to treat cuts, burns, ulcers, and other skin injuries, supporting the body's natural healing mechanisms and minimizing scarring.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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).