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Record Information
Version1.0
Created at2022-09-05 23:20:28 UTC
Updated at2022-09-05 23:20:28 UTC
NP-MRD IDNP0221694
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,3s,4s)-4-[(2r,3s)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-8-yl]-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol
DescriptionProdelphinidin B3 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''. (2r,3s,4s)-4-[(2r,3s)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-8-yl]-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol is found in Cistus incanus, Eucalyptus ovata, Platycarya strobilacea, Psidium guajava, Quercus dentata, Quercus robur, Ribes nigrum and Ziziphus spina-christi. It was first documented in 2013 (PMID: 23867167). Based on a literature review a significant number of articles have been published on Prodelphinidin B3 (PMID: 30381193) (PMID: 32545662) (PMID: 28934913) (PMID: 26103066).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC30H26O14
Average Mass610.5240 Da
Monoisotopic Mass610.13226 Da
IUPAC Name(2R,3S,4S)-4-[(2R,3S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Name(2R,3S,4S)-4-[(2R,3S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
CAS Registry NumberNot Available
SMILES
O[C@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C(O)=C1)C([C@H]1[C@H](O)[C@H](OC3=CC(O)=CC(O)=C13)C1=CC(O)=C(O)C(O)=C1)=C(O)C=C2O
InChI Identifier
InChI=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/t20-,24-,27-,28+,29+/m0/s1
InChI KeyRTEDIEITOBJPNI-MDPSILPBSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cistus incanusLOTUS Database
Eucalyptus ovataLOTUS Database
Platycarya strobilaceaLOTUS Database
Psidium guajavaLOTUS Database
Quercus dentataLOTUS Database
Quercus roburLOTUS Database
Ribes nigrumLOTUS Database
Ziziphus spina-christiLOTUS Database
Chemical Taxonomy
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
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavan-3-ol
  • Hydroxyflavonoid
  • Flavan
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Ether
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.51ChemAxon
pKa (Strongest Acidic)8.46ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area261.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity150.47 m³·mol⁻¹ChemAxon
Polarizability57.35 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00009116
Chemspider ID30822570
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProdelphinidin B3
METLIN IDNot Available
PubChem Compound13831068
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Rao S, Santhakumar AB, Chinkwo KA, Blanchard CL: Q-TOF LC/MS identification and UHPLC-Online ABTS antioxidant activity guided mapping of barley polyphenols. Food Chem. 2018 Nov 15;266:323-328. doi: 10.1016/j.foodchem.2018.06.011. Epub 2018 Jun 7. [PubMed:30381193 ]
  2. Irakli M, Lazaridou A, Mylonas I, Biliaderis CG: Bioactive Components and Antioxidant Activity Distribution in Pearling Fractions of Different Greek Barley Cultivars. Foods. 2020 Jun 12;9(6). pii: foods9060783. doi: 10.3390/foods9060783. [PubMed:32545662 ]
  3. Kohyama N, Chono M, Nakagawa H, Matsuo Y, Ono H, Matsunaka H: Flavonoid compounds related to seed coat color of wheat. Biosci Biotechnol Biochem. 2017 Nov;81(11):2112-2118. doi: 10.1080/09168451.2017.1373589. Epub 2017 Sep 22. [PubMed:28934913 ]
  4. Lv H, Yuan Z, Wang X, Wang Z, Suo Y, Wang H: Rapid Separation of Three Proanthocyanidin Dimers from Iris lactea Pall. var. Chinensis (Fisch.) Koidz by High-Speed Counter-Current Chromatography With Continuous Sample Load and Double-Pump Balancing Mode. Phytochem Anal. 2015 Nov-Dec;26(6):444-53. doi: 10.1002/pca.2579. Epub 2015 Jun 23. [PubMed:26103066 ]
  5. Suda M, Katoh M, Toda K, Matsumoto K, Kawaguchi K, Kawahara S, Hattori Y, Fujii H, Makabe H: Syntheses of procyanidin B2 and B3 gallate derivatives using equimolar condensation mediated by Yb(OTf)3 and their antitumor activities. Bioorg Med Chem Lett. 2013 Sep 1;23(17):4935-9. doi: 10.1016/j.bmcl.2013.06.061. Epub 2013 Jun 29. [PubMed:23867167 ]
  6. LOTUS database [Link]