Record Information
Version1.0
Creation date2010-04-08 22:10:13 UTC
Update date2019-11-26 03:06:56 UTC
Primary IDFDB012511
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTheaflavin
DescriptionIsotheaflavin belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Isotheaflavin is a moderately basic compound (based on its pKa). Isotheaflavin has been detected, but not quantified in, tea. This could make isotheaflavin a potential biomarker for the consumption of these foods.
CAS Number4670-05-7
Structure
Thumb
Synonyms
SynonymSource
1,8-Bis(3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy-5H-benzocyclohepten-5-one, 9CIdb_source
Theaflavinebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP1.84ALOGPS
logP2.83ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.73ChemAxon
pKa (Strongest Basic)2.89ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area217.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity144.27 m³·mol⁻¹ChemAxon
Polarizability55.97 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC29H24O12
IUPAC name3,4,6-trihydroxy-1,8-bis(3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)-5H-benzo[7]annulen-5-one
InChI IdentifierInChI=1S/C29H24O12/c30-11-3-17(32)15-8-21(36)28(40-23(15)5-11)10-1-13-14(7-20(35)27(39)25(13)26(38)19(34)2-10)29-22(37)9-16-18(33)4-12(31)6-24(16)41-29/h1-7,21-22,28-33,35-37,39H,8-9H2,(H,34,38)
InChI KeyIPMYMEWFZKHGAX-UHFFFAOYSA-N
Isomeric SMILESOC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C2=C1C=C(C=C(O)C2=O)C1OC2=CC(O)=CC(O)=C2CC1O
Average Molecular Weight564.4937
Monoisotopic Molecular Weight564.126776232
Classification
Description belongs to the class of organic compounds known as catechins. Catechins 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
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Benzopyran
  • Chromane
  • 1-benzopyran
  • Tropolone
  • Tropone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Vinylogous acid
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Foods
  • Cocoa and cocoa products
  • Nuts and legumes:

    Fruits and vegetables:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 61.70%; H 4.29%; O 34.01%DFC
    Melting PointMp 237-240° dec.DFC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV Data470 (e 3600) (EtOH) (Berdy)DFC
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash KeyView
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0601-2104129000-5f64bce1a9b74a8794c4JSpectraViewer
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0012-0105090000-dbad9256eefd5ac73cefJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0400190000-aba7cd070f494923cc4cJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901130000-19ff8617138242d42bbcJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0900110000-595c4e5339325a55cd10JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0100090000-b49c8ceebe73882cd9c5JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ri-0612790000-af02cca8665ff5d8bce7JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1901020000-421f10b24f466f3fd655JSpectraViewer
    ChemSpider ID17216345
    ChEMBL IDNot Available
    KEGG Compound IDNot Available
    Pubchem Compound ID22833651
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID133
    DrugBank IDNot Available
    HMDB IDHMDB05788
    CRC / DFC (Dictionary of Food Compounds) IDHHP83-R:HHP83-R
    EAFUS IDNot Available
    Dr. Duke IDTHEAFLAVIN
    BIGG IDNot Available
    KNApSAcK IDC00009348
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDTheaflavin
    Phenol-Explorer Metabolite ID133
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
    anti carcinogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
    anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
    fungicide24127 A substance used to destroy fungal pests.DUKE
    lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
    mitogen52290 A chemical substance that encourages a cell to commence cell division, triggering mitosis.DUKE
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
    — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.