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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:41:08 UTC
Update Date2019-07-23 06:31:36 UTC
HMDB IDHMDB0040140
Secondary Accession Numbers
  • HMDB40140
Metabolite Identification
Common Name8,8'-Methylenebiscatechin
Description8,8'-Methylenebiscatechin is found in cocoa and cocoa products. 8,8'-Methylenebiscatechin is a constituent of cacao liquor, Theobroma cacao.
Structure
Data?1563863496
Synonyms
ValueSource
Bis-8,8'-catechinylmethaneHMDB
Di(8-catechinyl)methaneHMDB
Chemical FormulaC31H28O12
Average Molecular Weight592.5468
Monoisotopic Molecular Weight592.15807636
IUPAC Name(2R,3S)-2-(3,4-dihydroxyphenyl)-8-{[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]methyl}-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Name(2R,3S)-2-(3,4-dihydroxyphenyl)-8-{[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]methyl}-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
CAS Registry Number81555-08-0
SMILES
O[C@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C=C1)C(CC1=C(O)C=C(O)C3=C1O[C@@H]([C@@H](O)C3)C1=CC=C(O)C(O)=C1)=C(O)C=C2O
InChI Identifier
InChI=1S/C31H28O12/c32-18-3-1-12(5-24(18)38)28-26(40)8-16-22(36)10-20(34)14(30(16)42-28)7-15-21(35)11-23(37)17-9-27(41)29(43-31(15)17)13-2-4-19(33)25(39)6-13/h1-6,10-11,26-29,32-41H,7-9H2/t26-,27-,28+,29+/m0/s1
InChI KeyKATSZCAOGZFWJD-QUAHOIDUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as catechins. These are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechins
Alternative Parents
Substituents
  • Catechin
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Resorcinol
  • 1,2-diphenol
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

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 Solubility0.054 g/LALOGPS
logP2.17ALOGPS
logP3.71ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)7.63ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area220.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity151.68 m³·mol⁻¹ChemAxon
Polarizability58.6 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0901370000-674efc52664a74afe5dcJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9300034000-8c426fab30ddcf546f7dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0111690000-ca73f2473687585e386fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f76-0652940000-9c5f085063af7774347eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-0890320000-29d82464b5ace40fd570JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0010090000-a76ab9da3f11ff095069JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-0930240000-21a9df8d43112e967dc6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0890210000-8e0673852242e9a8a4c2JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 ID197
FoodDB IDFDB019837
KNApSAcK IDC00036803
Chemspider ID30777478
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound46182787
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.. .