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Showing Compound Procyanidin B2 8-C-glucoside (FDB016449)

Record Information
Version1.0
Creation date2010-04-08 22:12:26 UTC
Update date2019-11-26 03:13:15 UTC
Primary IDFDB016449
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProcyanidin B2 8-C-glucoside
Description8-Glucopyranosylprocyanidin B2 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''. 8-Glucopyranosylprocyanidin B2 has been detected, but not quantified in, a few different foods, such as chinese cinnamons (Cinnamomum aromaticum), green vegetables, and herbs and spices. This could make 8-glucopyranosylprocyanidin B2 a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 8-Glucopyranosylprocyanidin B2.
CAS Number103215-58-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.17 g/LALOGPS
logP1.21ALOGPS
logP0.36ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)8.6ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area310.91 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity179.63 m³·mol⁻¹ChemAxon
Polarizability71.8 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC36H36O17
IUPAC name(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
InChI IdentifierInChI=1S/C36H36O17/c37-10-23-28(47)30(49)31(50)36(51-23)26-21(45)9-20(44)25-27(29(48)33(53-35(25)26)12-2-4-15(39)18(42)6-12)24-19(43)8-16(40)13-7-22(46)32(52-34(13)24)11-1-3-14(38)17(41)5-11/h1-6,8-9,22-23,27-33,36-50H,7,10H2/t22-,23-,27+,28-,29-,30+,31-,32-,33-,36+/m1/s1
InChI KeyJBDZOCOBUGXPJW-LYGYLKCLSA-N
Isomeric SMILESOC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2O[C@@H]([C@H](O)[C@@H](C3=C(O)C=C(O)C4=C3O[C@@H]([C@H](O)C4)C3=CC=C(O)C(O)=C3)C2=C(O)C=C1O)C1=CC=C(O)C(O)=C1
Average Molecular Weight740.6608
Monoisotopic Molecular Weight740.195249726
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
  • Flavonoid c-glycoside
  • Flavonoid-8-c-glycoside
  • Catechin
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavan-3-ol
  • Flavan
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • C-glycosyl compound
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monosaccharide
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_1_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_1_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_1_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_1_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_1_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcyanidin B2 8-C-glucoside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00du-0100080900-22a7764e6930dfcc054b2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02mr-0300593400-0c5be904e4f2160fe01e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kg9-0100932100-0ba9d47992cf3eb854042016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000022900-05df8dfcbeebd0bcb5fb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-3950213400-0738f65d549be4cd0cfd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-5595013100-0a4c6723ab0efc06de042016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0000000900-41ae947ab44323ae78f62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0430066900-4235ed27d433e7ac5f7d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-2400039100-80502cb0789c115101bc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000002900-e978dd7b87634cf91d082021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abi-1000039600-0ab288f5818ec21ab3012021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-3970168700-43cef26667cb764b2a472021-09-22View Spectrum
NMRNot Available
ChemSpider ID10272882
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID21637579
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37405
CRC / DFC (Dictionary of Food Compounds) IDKRG02-Y:KRG03-Z
EAFUS IDNot Available
Dr. Duke IDPROCYANIDIN-B28-BETA-D-GLUCOPYRANOSIDE
BIGG IDNot Available
KNApSAcK IDC00006327
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.