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 Date2012-09-12 00:12:17 UTC
Update Date2022-03-07 02:55:57 UTC
HMDB IDHMDB0038857
Secondary Accession Numbers
  • HMDB38857
Metabolite Identification
Common NameEpicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin
DescriptionEpicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin has been detected, but not quantified in, fruits and lingonberries. This could make epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin a potential biomarker for the consumption of these foods.
Structure
Data?1563863270
Synonyms
ValueSource
Epicatechin-(4b->8)-epicatechin-(2b->7,4b->8)-catechinGenerator
Epicatechin-(4β->8)-epicatechin-(2β->7,4β->8)-catechinGenerator
Chemical FormulaC45H36O18
Average Molecular Weight864.7565
Monoisotopic Molecular Weight864.190164348
IUPAC Name(1R,5R,6S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol
Traditional Name(1R,5R,6S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol
CAS Registry Number114637-81-9
SMILES
O[C@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C1=C(O[C@@]3(OC4=C([C@H]1[C@H]3O)C(O)=CC(O)=C4[C@@H]1[C@@H](O)[C@H](OC3=C1C(O)=CC(O)=C3)C1=CC(O)=C(O)C=C1)C1=CC(O)=C(O)C=C1)C=C2O
InChI Identifier
InChI=1S/C45H36O18/c46-18-10-27(54)33-31(11-18)60-41(16-2-5-21(48)25(52)8-16)39(58)37(33)34-28(55)13-29(56)35-38-36-32(62-45(44(38)59,63-43(34)35)17-3-6-22(49)26(53)9-17)14-23(50)19-12-30(57)40(61-42(19)36)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37+,38+,39+,40+,41+,44+,45+/m0/s1
InChI KeySRWJAXVAWDYXPA-ACNGEOCHSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • A-type proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Proanthocyanidin
  • Catechin
  • Pyranoflavonoid
  • 3'-hydroxyflavonoid
  • Flavan-3-ol
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavan
  • Pyranochromene
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Catechol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Ketal
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Acetal
  • 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
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 Solubility0.16 g/LALOGPS
logP3.54ALOGPS
logP4.91ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.62ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area320.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity216.7 m³·mol⁻¹ChemAxon
Polarizability85.1 ųChemAxon
Number of Rings10ChemAxon
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]+262.96330932474
DeepCCS[M-H]-261.2430932474
DeepCCS[M-2H]-295.27230932474
DeepCCS[M+Na]+269.2130932474
AllCCS[M+H]+282.732859911
AllCCS[M+H-H2O]+282.632859911
AllCCS[M+NH4]+282.832859911
AllCCS[M+Na]+282.832859911
AllCCS[M-H]-273.132859911
AllCCS[M+Na-2H]-277.532859911
AllCCS[M+HCOO]-282.432859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin 10V, Positive-QTOFsplash10-0292-0211003490-5e8202baa406f6e2b8092016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin 20V, Positive-QTOFsplash10-06r5-0600084940-12702116800f0231763d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin 40V, Positive-QTOFsplash10-0a4i-0910020120-eb3715bfc9597cc57ec82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin 10V, Negative-QTOFsplash10-03di-0111000290-14f0e1f3d1b46e11e7892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin 20V, Negative-QTOFsplash10-0w2j-0920140440-5569684c6657178fce022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin 40V, Negative-QTOFsplash10-002r-0950000000-537693c7d834b9dd24ae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin 10V, Negative-QTOFsplash10-03di-0000000090-41b280e1fc4a1866093a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin 20V, Negative-QTOFsplash10-03di-0000000590-1bf5402cb6770200c9382021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin 40V, Negative-QTOFsplash10-03g0-0120001940-9eca3ded1c03f84a814d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin 10V, Positive-QTOFsplash10-014i-0000000190-5978ab4e7ddf229ec2b62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin 20V, Positive-QTOFsplash10-014l-0200020890-ade1fcf049b10b7c9d512021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin 40V, Positive-QTOFsplash10-05fr-1920000560-2ba5b1ad52b9f8eefac52021-09-25Wishart 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 IDFDB018296
KNApSAcK IDC00009299
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10350652
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.. .