Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:39:01 UTC
Update Date2022-03-07 02:55:19 UTC
HMDB IDHMDB0037405
Secondary Accession Numbers
  • HMDB37405
Metabolite Identification
Common Name8-Glucopyranosylprocyanidin B2
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.
Structure
Data?1563863025
Synonyms
ValueSource
8-C-Glucopyranosylprocyanidin b2HMDB
Chemical FormulaC36H36O17
Average Molecular Weight740.6608
Monoisotopic Molecular Weight740.195249726
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
Traditional 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
CAS Registry Number103215-58-3
SMILES
OC[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
InChI Identifier
InChI=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
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
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+260.14330932474
DeepCCS[M-H]-258.4230932474
DeepCCS[M-2H]-292.82930932474
DeepCCS[M+Na]+266.47230932474
AllCCS[M+H]+261.432859911
AllCCS[M+H-H2O]+260.832859911
AllCCS[M+NH4]+262.032859911
AllCCS[M+Na]+262.232859911
AllCCS[M-H]-265.132859911
AllCCS[M+Na-2H]-269.232859911
AllCCS[M+HCOO]-273.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-Glucopyranosylprocyanidin B2OC[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)=C17358.1Standard polar33892256
8-Glucopyranosylprocyanidin B2OC[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)=C16188.0Standard non polar33892256
8-Glucopyranosylprocyanidin B2OC[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)=C17026.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 10V, Positive-QTOFsplash10-00du-0100080900-22a7764e6930dfcc054b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 20V, Positive-QTOFsplash10-02mr-0300593400-0c5be904e4f2160fe01e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 40V, Positive-QTOFsplash10-0kg9-0100932100-0ba9d47992cf3eb854042016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 10V, Negative-QTOFsplash10-000i-0000022900-05df8dfcbeebd0bcb5fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 20V, Negative-QTOFsplash10-0079-3950213400-0738f65d549be4cd0cfd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 40V, Negative-QTOFsplash10-00kr-5595013100-0a4c6723ab0efc06de042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 10V, Positive-QTOFsplash10-006x-0000000900-41ae947ab44323ae78f62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 20V, Positive-QTOFsplash10-00dl-0430066900-4235ed27d433e7ac5f7d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 40V, Positive-QTOFsplash10-05fr-2400039100-80502cb0789c115101bc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 10V, Negative-QTOFsplash10-000i-0000002900-e978dd7b87634cf91d082021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 20V, Negative-QTOFsplash10-0abi-1000039600-0ab288f5818ec21ab3012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 40V, Negative-QTOFsplash10-000l-3970168700-43cef26667cb764b2a472021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016449
KNApSAcK IDC00006327
Chemspider ID10272882
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21637579
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .