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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:14:15 UTC
Update Date2022-03-07 02:55:34 UTC
HMDB IDHMDB0037967
Secondary Accession Numbers
  • HMDB37967
Metabolite Identification
Common Name3,3'-Digalloylprocyanidin B2
Description3,3'-Digalloylprocyanidin 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''. 3,3'-Digalloylprocyanidin B2 has been detected, but not quantified in, several different foods, such as green tea, herbal tea, green vegetables, red tea, and common grapes (Vitis vinifera). This could make 3,3'-digalloylprocyanidin B2 a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,3'-Digalloylprocyanidin B2.
Structure
Data?1563863117
Synonyms
ValueSource
3-O-Galloylepicatechin-(4beta->8)-epicatechin-3-O-gallateHMDB
Proanthocyanidin b2 3,3'-O-gallateHMDB
Procyanidin b2 3,3'-di-O-gallateHMDB
Procyanidin b2-3,3'-di-O-gallateMeSH, HMDB
(2R,3R)-2-(3,4-Dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acidGenerator
Proanthocyanidin b2 3,3'-digallic acidGenerator
Chemical FormulaC44H34O20
Average Molecular Weight882.7288
Monoisotopic Molecular Weight882.164343528
IUPAC Name(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
CAS Registry Number79907-44-1
SMILES
OC1=CC(O)=C2[C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC=C(O)C(O)=C1)C1=C2O[C@@H]([C@@H](CC2=C(O)C=C1O)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C44H34O20/c45-19-11-26(51)34-32(12-19)61-40(16-2-4-22(47)25(50)6-16)42(64-44(60)18-9-30(55)38(58)31(56)10-18)36(34)35-27(52)14-23(48)20-13-33(62-43(59)17-7-28(53)37(57)29(54)8-17)39(63-41(20)35)15-1-3-21(46)24(49)5-15/h1-12,14,33,36,39-40,42,45-58H,13H2/t33-,36-,39-,40-,42-/m1/s1
InChI KeyKTLUHRSHFRODPS-RIQPQZJCSA-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
  • Proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Catechin gallate
  • Catechin
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 3'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavan
  • Galloyl ester
  • Gallic acid or derivatives
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid alkyl ester
  • Benzoate ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Benzoyl
  • Catechol
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Polyol
  • Ether
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • 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 Solubility0.11 g/LALOGPS
logP3.9ALOGPS
logP6.28ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)7.77ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area354.28 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity218.04 m³·mol⁻¹ChemAxon
Polarizability83.51 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+265.25730932474
DeepCCS[M-H]-263.53330932474
DeepCCS[M-2H]-297.56630932474
DeepCCS[M+Na]+271.42830932474
AllCCS[M+H]+281.332859911
AllCCS[M+H-H2O]+281.332859911
AllCCS[M+NH4]+281.332859911
AllCCS[M+Na]+281.332859911
AllCCS[M-H]-270.132859911
AllCCS[M+Na-2H]-274.132859911
AllCCS[M+HCOO]-278.532859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 10V, Positive-QTOFsplash10-0h0r-0510090450-397db369cb5854acd45f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 20V, Positive-QTOFsplash10-0f6x-0941260210-03ac03f6d42738a5f1982016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 40V, Positive-QTOFsplash10-0zfr-0981110010-928d1c64ced9334e42602016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 10V, Negative-QTOFsplash10-001i-0300000390-b8be6162d05537078f362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 20V, Negative-QTOFsplash10-0gdi-0903100430-a69a03fb5779753ab28e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 40V, Negative-QTOFsplash10-016r-0900001000-34b545b4afc98d2d4ec12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 10V, Negative-QTOFsplash10-0043-0090600580-bda7af02a32c22ca6e1e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 20V, Negative-QTOFsplash10-03di-0200000690-3409a8495fb4fdaf73042021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 40V, Negative-QTOFsplash10-004i-1900000360-9b9ea0ecf9a2af888ffc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 10V, Positive-QTOFsplash10-02ai-0100003980-43ce8ef4caabdf9635792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 20V, Positive-QTOFsplash10-003u-0210311390-530307e1a46cd4e3d7c42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 40V, Positive-QTOFsplash10-05rr-0400040590-7b1370f207f6cbff3c2c2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB017141
KNApSAcK IDC00009213
Chemspider ID110532
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound124016
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.. .