Showing metabocard for Theaflavin (BMDB0005788)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:18:31 UTC
Update Date2020-04-22 15:16:19 UTC
BMDB IDBMDB0005788
Secondary Accession Numbers
  • BMDB05788
Metabolite Identification
Common NameTheaflavin
DescriptionTheaflavin belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4. Theaflavin is a very strong basic compound (based on its pKa).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC29H24O12
Average Molecular Weight564.4937
Monoisotopic Molecular Weight564.126776232
IUPAC Name3,4,6-trihydroxy-2,8-bis[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-5H-benzo[7]annulen-5-one
Traditional Name3,4,6-trihydroxy-2,8-bis[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]benzo[7]annulen-5-one
CAS Registry Number4670-05-7
SMILES
O[C@@H]1CC2=C(O[C@@H]1C1=CC3=C(C(O)=C1O)C(=O)C(O)=CC(=C3)[C@H]1OC3=C(C[C@H]1O)C(O)=CC(O)=C3)C=C(O)C=C2O
InChI Identifier
InChI=1S/C29H24O12/c30-12-4-17(32)14-8-20(35)28(40-22(14)6-12)11-1-10-2-16(25(37)27(39)24(10)26(38)19(34)3-11)29-21(36)9-15-18(33)5-13(31)7-23(15)41-29/h1-7,20-21,28-33,35-37,39H,8-9H2,(H,34,38)/t20-,21-,28-,29-/m1/s1
InChI KeyMKTFRRIBCBTOKJ-CRFHJIRQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavan-3-ols
Alternative Parents
Substituents
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavan-3-ol
  • Hydroxyflavonoid
  • 1-benzopyran
  • Chromane
  • Benzopyran
  • Tropolone
  • Tropone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Secondary alcohol
  • Cyclic ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.87ALOGPS
logP2.83ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)2.9ChemAxon
pKa (Strongest Basic)7.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area217.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity144.27 m³·mol⁻¹ChemAxon
Polarizability55.15 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000b-0104090000-9964fe78bdf8ad431d30View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0l6r-1100629000-9802132cb2711f994363View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0401190000-2ddc76099df2281a9217View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901130000-36ded695f5ec5f38b6c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0900110000-fde4fbd1ff8bb9b5ae9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0100090000-d177c4b4f41d66f7ee1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-0612790000-6758fac93650fc9b7736View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1901020000-5e2c48fe087f75262d93View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0005788
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTheaflavin
METLIN IDNot Available
PubChem Compound22833651
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceTanaka, Takashi; Betsumiya, Yayoi; Mine, Chie; Kouno, Isao. Theanaphthoquinone, a novel pigment oxidatively derived from theaflavin during tea-fermentation. Chemical Communications (Cambridge) (2000), (15), 1365-1366.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available