Survey with prize
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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:10 UTC
Update Date2019-07-23 06:10:06 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 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.
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
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015i-0000019060-9e5fea4c16ac3b3d4f77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03yi-0000098220-595def5c95b05bac42efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-0000859210-3985f0b3a2ee0431f524Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0100012190-993fb87f61144ae0ab3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0il0-0940051420-5dae6575d08e7ae03ae0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0890003200-5766a6e717bd7c02387aSpectrum
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 IDFDB008701
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
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