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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:10 UTC
Update Date2022-03-07 02:53:12 UTC
HMDB IDHMDB0032006
Secondary Accession Numbers
  • HMDB32006
Metabolite Identification
Common NameEpifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol
DescriptionEpifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol 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''. Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol has been detected, but not quantified in, fruits. This could make epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol.
Structure
Data?1563862205
Synonyms
ValueSource
Epifisetinidol-(4b->8)-epicatechin-(6->4b)-epifisetinidolGenerator
Epifisetinidol-(4β->8)-epicatechin-(6->4β)-epifisetinidolGenerator
Epifisetinidol(4b->8)epicatechin(6->4b)epifisetinidolHMDB
Chemical FormulaC45H38O16
Average Molecular Weight834.7736
Monoisotopic Molecular Weight834.215985168
IUPAC Name2-(3,4-dihydroxyphenyl)-6,8-bis[2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Name2-(3,4-dihydroxyphenyl)-6,8-bis[2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
CAS Registry NumberNot Available
SMILES
OC1CC2=C(O)C(C3C(O)C(OC4=CC(O)=CC=C34)C3=CC(O)=C(O)C=C3)=C(O)C(C3C(O)C(OC4=CC(O)=CC=C34)C3=CC(O)=C(O)C=C3)=C2OC1C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C45H38O16/c46-20-4-6-22-32(14-20)59-43(18-2-9-26(49)29(52)12-18)40(57)34(22)36-38(55)24-16-31(54)42(17-1-8-25(48)28(51)11-17)61-45(24)37(39(36)56)35-23-7-5-21(47)15-33(23)60-44(41(35)58)19-3-10-27(50)30(53)13-19/h1-15,31,34-35,40-44,46-58H,16H2
InChI KeyVYURQCQMACPHRC-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
  • Bi- and polyflavonoid skeleton
  • Proanthocyanidin
  • Catechin
  • Flavan-3-ol
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • Flavan
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Catechol
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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
logP3.75ALOGPS
logP5.04ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.69ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area290.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity215.05 m³·mol⁻¹ChemAxon
Polarizability84 ųChemAxon
Number of Rings9ChemAxon
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-2H]-310.92830932474
DeepCCS[M+Na]+285.32130932474
AllCCS[M+H]+278.332859911
AllCCS[M+H-H2O]+278.132859911
AllCCS[M+NH4]+278.332859911
AllCCS[M+Na]+278.332859911
AllCCS[M-H]-267.232859911
AllCCS[M+Na-2H]-271.132859911
AllCCS[M+HCOO]-275.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidolOC1CC2=C(O)C(C3C(O)C(OC4=CC(O)=CC=C34)C3=CC(O)=C(O)C=C3)=C(O)C(C3C(O)C(OC4=CC(O)=CC=C34)C3=CC(O)=C(O)C=C3)=C2OC1C1=CC(O)=C(O)C=C19745.3Standard polar33892256
Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidolOC1CC2=C(O)C(C3C(O)C(OC4=CC(O)=CC=C34)C3=CC(O)=C(O)C=C3)=C(O)C(C3C(O)C(OC4=CC(O)=CC=C34)C3=CC(O)=C(O)C=C3)=C2OC1C1=CC(O)=C(O)C=C15638.9Standard non polar33892256
Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidolOC1CC2=C(O)C(C3C(O)C(OC4=CC(O)=CC=C34)C3=CC(O)=C(O)C=C3)=C(O)C(C3C(O)C(OC4=CC(O)=CC=C34)C3=CC(O)=C(O)C=C3)=C2OC1C1=CC(O)=C(O)C=C18531.1Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol 10V, Positive-QTOFsplash10-015i-0000019060-9e5fea4c16ac3b3d4f772015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol 20V, Positive-QTOFsplash10-03yi-0000098220-595def5c95b05bac42ef2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol 40V, Positive-QTOFsplash10-00kb-0000859210-3985f0b3a2ee0431f5242015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol 10V, Negative-QTOFsplash10-001i-0100012190-993fb87f61144ae0ab3a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol 20V, Negative-QTOFsplash10-0il0-0940051420-5dae6575d08e7ae03ae02015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol 40V, Negative-QTOFsplash10-00di-0890003200-5766a6e717bd7c02387a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol 10V, Negative-QTOFsplash10-001i-0000020090-bee1326e71a92eff3e3f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol 20V, Negative-QTOFsplash10-001i-0000001940-a5fee26436aa46bda4c92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol 40V, Negative-QTOFsplash10-03gr-0340042930-380287cb2263c9cc4b192021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol 10V, Positive-QTOFsplash10-002r-0000000490-46ac4727c9dcfba234dd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol 20V, Positive-QTOFsplash10-03dr-0500024970-4a487925c33a3b3933362021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol 40V, Positive-QTOFsplash10-0f79-0910002320-d1aaf953fc083fd990d62021-09-25Wishart 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 IDFDB008702
KNApSAcK IDNot Available
Chemspider ID4265737
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5089686
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:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol → 6,8-bis[2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-trioldetails
Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol → 8-[3,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-2-(3,4-dihydroxyphenyl)-6-[2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-trioldetails
Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol → 6-[3,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-2-(3,4-dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-trioldetails
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol → [2-(3,4-dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-6-[2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]oxidanesulfonic aciddetails
Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol → [2-(3,4-dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-6-yl]-7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]oxidanesulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol → 6-(5-{6,8-bis[2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl}-2-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol → 6-{[2-(3,4-dihydroxyphenyl)-6,8-bis[2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,5-dihydroxy-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol → (5-{6,8-bis[2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl}-2-hydroxyphenyl)oxidanesulfonic aciddetails
Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol → (5-{4-[2-(3,4-dihydroxyphenyl)-6-[2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl}-2-hydroxyphenyl)oxidanesulfonic aciddetails
Epifisetinidol-(4beta->8)-epicatechin-(6->4beta)-epifisetinidol → (5-{4-[2-(3,4-dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-6-yl]-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl}-2-hydroxyphenyl)oxidanesulfonic aciddetails