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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:53:55 UTC
Update Date2022-03-07 02:55:26 UTC
HMDB IDHMDB0037649
Secondary Accession Numbers
  • HMDB37649
Metabolite Identification
Common Name3,3'-Digalloylprodelphinidin B2
Description3,3'-Digalloylprodelphinidin 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'-Digalloylprodelphinidin B2 has been detected, but not quantified in, several different foods, such as red tea, teas (Camellia sinensis), fruits, black tea, and herbal tea. This could make 3,3'-digalloylprodelphinidin B2 a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,3'-Digalloylprodelphinidin B2.
Structure
Data?1563863066
Synonyms
ValueSource
3-O-Galloylepigallocatechin-(4beta->8)-epigallocatechin-3-O-gallateHMDB
RhodisinHMDB
8-[5,7-Dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acidGenerator
Prodelphinidin b2 3,3'-digallic acidGenerator
Chemical FormulaC44H34O22
Average Molecular Weight914.7276
Monoisotopic Molecular Weight914.154172772
IUPAC Name4-[5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name4-[5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
CAS Registry Number86588-89-8
SMILES
OC1=CC(O)=C2C(C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C(OC2=C1)C1=CC(O)=C(O)C(O)=C1)C1=C(O)C=C(O)C2=C1OC(C(C2)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1S/C44H34O22/c45-17-9-20(47)32-30(10-17)63-40(14-3-24(51)36(58)25(52)4-14)42(66-44(62)16-7-28(55)38(60)29(56)8-16)34(32)33-21(48)12-19(46)18-11-31(64-43(61)15-5-26(53)37(59)27(54)6-15)39(65-41(18)33)13-1-22(49)35(57)23(50)2-13/h1-10,12,31,34,39-40,42,45-60H,11H2
InChI KeyOBAZBWUNTJYECH-UHFFFAOYSA-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
  • Epigallocatechin
  • Catechin
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-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
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility0.2 g/LALOGPS
logP3.62ALOGPS
logP5.68ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.75ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area394.74 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity222 m³·mol⁻¹ChemAxon
Polarizability85.98 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]+276.57430932474
DeepCCS[M-H]-274.8530932474
DeepCCS[M-2H]-308.88430932474
DeepCCS[M+Na]+282.90330932474
AllCCS[M+H]+283.332859911
AllCCS[M+H-H2O]+283.432859911
AllCCS[M+NH4]+283.232859911
AllCCS[M+Na]+283.132859911
AllCCS[M-H]-279.732859911
AllCCS[M+Na-2H]-283.932859911
AllCCS[M+HCOO]-288.632859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprodelphinidin B2 10V, Positive-QTOFsplash10-0002-0300090413-2212333ef0741d44ae802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprodelphinidin B2 20V, Positive-QTOFsplash10-0zi3-0860792210-c2e728dad2420450fc7e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprodelphinidin B2 40V, Positive-QTOFsplash10-0zfr-0890210010-e8e4fe4da1e2719526952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprodelphinidin B2 10V, Negative-QTOFsplash10-03di-0300000419-0cec9a519df9b3a9f37f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprodelphinidin B2 20V, Negative-QTOFsplash10-016r-0904110731-98e247d05952e6c7a3782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprodelphinidin B2 40V, Negative-QTOFsplash10-016r-0901000200-d6d3a73350debbbab7a92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprodelphinidin B2 10V, Negative-QTOFsplash10-03di-0000000109-fd02fd29e76c206549882021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprodelphinidin B2 20V, Negative-QTOFsplash10-03dv-0300010973-4501981fad5a6693c4ea2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprodelphinidin B2 40V, Negative-QTOFsplash10-004i-0901300170-217cc8bfa235cfea17512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprodelphinidin B2 10V, Positive-QTOFsplash10-00ks-0000004911-b9bb2485c9f0e908a5e52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprodelphinidin B2 20V, Positive-QTOFsplash10-0aor-0731900475-a6de84e6ee664f7a5b6e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3'-Digalloylprodelphinidin B2 40V, Positive-QTOFsplash10-0pvl-0420030391-cf419cf1c773715cab012021-09-25Wishart 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 IDFDB016765
KNApSAcK IDC00009239
Chemspider ID35014447
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13270041
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.. .

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
3,3'-Digalloylprodelphinidin B2 → 3'-Galloylprodelphinidin B2details