CHEBI:136609 - theaflavin

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ChEBI Name theaflavin
ChEBI ID CHEBI:136609
Definition A biflavonoid that is 3,4,5-trihydroxybenzocyclohepten-6-one which is substituted at positions 1 and 8 by (2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl groups. It is the main red pigment in black tea.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C29H24O12
Net Charge 0
Average Mass 564.495
Monoisotopic Mass 564.12678
InChI InChI=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)/t21-,22-,28-,29-/m1/s1
InChIKey IPMYMEWFZKHGAX-ZKSIBHASSA-N
SMILES [C@@]1(OC=2C=C(O)C=C(O)C2C[C@H]1O)([H])C3=CC(=O)C(=C4C(=C3)C([C@]5(OC=6C=C(O)C=C(O)C6C[C@H]5O)[H])=CC(O)=C4O)O
Metabolite of Species Details
Camellia sinensis (NCBI:txid4442) Found in leaf (BTO:0000713). See: Tetrahedron, 1973, v29, 125
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
chelator
A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
Application(s): radiation protective agent

View more via ChEBI Ontology
ChEBI Ontology
Outgoing theaflavin (CHEBI:136609) has role antibacterial agent (CHEBI:33282)
theaflavin (CHEBI:136609) has role antioxidant (CHEBI:22586)
theaflavin (CHEBI:136609) has role chelator (CHEBI:38161)
theaflavin (CHEBI:136609) has role plant metabolite (CHEBI:76924)
theaflavin (CHEBI:136609) has role radiation protective agent (CHEBI:66987)
theaflavin (CHEBI:136609) is a biflavonoid (CHEBI:50128)
theaflavin (CHEBI:136609) is a polyphenol (CHEBI:26195)
IUPAC Name
3,4,5-trihydroxy-1,8-bis[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]-6H-benzocyclohepten-6-one
Synonyms Sources
(−)-theaflavin ChEBI
1,8-bis((2R,3R)-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy-5H-benzocyclohepten-5-one ChemIDplus
1,8-bis(3-α,5,7-trihydroxy-2-α-chromanyl)-5H-benzocyclohepten-5-one ChemIDplus
3,4,5-trihydroxy-1,8-bis[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]-6H-benzo[7]annulen-6-one IUPAC
theaflavine ChemIDplus
Manual Xrefs Databases
102754 ChemSpider
C00009348 KNApSAcK
FDB012511 FooDB
HMDB0005788 HMDB
KR20080052675 Patent
Theaflavin Wikipedia
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Registry Numbers Types Sources
25497520 Reaxys Registry Number Reaxys
4670-05-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
26386739 PubMed citation Europe PMC
26851019 PubMed citation Europe PMC
27237789 PubMed citation Europe PMC
27756182 PubMed citation Europe PMC
27838465 PubMed citation Europe PMC
28190756 PubMed citation Europe PMC
28381812 PubMed citation Europe PMC
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28939421 PubMed citation Europe PMC
Last Modified
15 January 2018