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Prodelphinidin B3 (FDB016774)

Record Information
Version1.0
Creation date2010-04-08 22:12:38 UTC
Update date2019-11-26 03:13:46 UTC
Primary IDFDB016774
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProdelphinidin B3
DescriptionProdelphinidin b3 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''. Prodelphinidin b3 is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Prodelphinidin b3 can be found in a number of food items such as broad bean, italian sweet red pepper, cucurbita (gourd), and green zucchini, which makes prodelphinidin b3 a potential biomarker for the consumption of these food products.
CAS Number110115-59-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP2.22ALOGPS
logP2.81ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)8.56ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area240.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity148.49 m³·mol⁻¹ChemAxon
Polarizability58.27 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC30H26O14
IUPAC name(2R,3S,4S)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
InChI IdentifierInChI=1S/C30H26O14/c31-11-5-14(33)22-21(6-11)43-29(10-3-18(37)26(41)19(38)4-10)27(42)24(22)23-15(34)8-13(32)12-7-20(39)28(44-30(12)23)9-1-16(35)25(40)17(36)2-9/h1-6,8,20,24,27-29,31-42H,7H2
InChI KeyRTEDIEITOBJPNI-UHFFFAOYSA-N
Isomeric SMILESOC1CC2=C(O)C=C(O)C(C3C(O)C(OC4=CC(O)=CC(O)=C34)C3=CC(O)=C(O)C(O)=C3)=C2OC1C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight610.519
Monoisotopic Molecular Weight610.13225554
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
  • 3'-hydroxyflavonoid
  • Flavan-3-ol
  • Hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavan
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Benzenetriol
  • Pyrogallol derivative
  • Catechol
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.02%; H 4.29%; O 36.69%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -146 (c, 0.05 in MeOH aq.)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, Positivesplash10-004j-0210980000-c1f8ae51d3afab5b73782017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0645920000-cf118f50982fe9ad76372017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002o-0690110000-7d7bf8ff0cdba3de35072017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0100290000-8266b1bc83f1c5cfcb302017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0921220000-9b2462cc181767bb7a8a2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0901000000-15bcb361ba549a2d50b12017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000290000-569e5cd826aaf0d0ee0b2021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-0010690000-89c42448532da7a61a432021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0902670000-dd37c53e6a95204bfb8c2021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000090000-d0a28a905b0faeed4e652021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mo-0000390000-add39244d120b7c3f4982021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adr-0330290000-e5196e15877872627ac12021-10-22View 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 ID156
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDKTF13-L:KTF28-T
EAFUS IDNot Available
Dr. Duke IDGALLOCATECHIN-(4ALPHA->8)-GALLOCATECHIN|(+)-GALLOCATECHIN-(4-ALPHA-8)-GALLOCATECHIN|GALLOCATECHIN-(4,8)-GALLOCATECHIN|PRODELPHINIDIN-B-3-DIMER|PRODELPHINIDIN-B-3
BIGG IDNot Available
KNApSAcK IDC00009116
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 inflammatory35472 A substance that reduces or suppresses inflammation.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— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.