7-O-galloyltricetiflavan (CHEBI:65943)

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ChEBI Name	7-O-galloyltricetiflavan

ChEBI ID	CHEBI:65943

ChEBI ASCII Name	7-O-galloyltricetiflavan

Definition	A gallate ester obtained by the formal condensation of gallic acid with the hydroxy group at position 7 of 3',4',5',5,7-pentahydroxyflavan. Isolated from the leaves of Pithecellobium clypearia, it exhibits antiviral activity.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C22H18O10

Net Charge

Average Mass

442.37230

Monoisotopic Mass

442.09000

InChI

InChI=1S/C22H18O10/c23-13-7-11(31-22(30)10-5-16(26)21(29)17(27)6-10)8-19-12(13)1-2-18(32-19)9-3-14(24)20(28)15(25)4-9/h3-8,18,23-29H,1-2H2

InChIKey

XQLJWQWRTLHKGO-UHFFFAOYSA-N

SMILES

Oc1cc(cc(O)c1O)C1CCc2c(O)cc(OC(=O)c3cc(O)c(O)c(O)c3)cc2O1

Metabolite of Species	Details
Pithecellobium clypearia (NCBI:txid714486)	Found in leaf (BTO:0000713). See: PubMed

Roles Classification
Biological Role(s):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. antiviral agent A substance that destroys or inhibits replication of viruses.

ChEBI Ontology
Outgoing	7-O-galloyltricetiflavan (CHEBI:65943) has functional parent flavan (CHEBI:38691) 7-O-galloyltricetiflavan (CHEBI:65943) has role antiviral agent (CHEBI:22587) 7-O-galloyltricetiflavan (CHEBI:65943) has role metabolite (CHEBI:25212) 7-O-galloyltricetiflavan (CHEBI:65943) is a gallate ester (CHEBI:37576) 7-O-galloyltricetiflavan (CHEBI:65943) is a tetrahydroxyflavan (CHEBI:72011)

IUPAC Name

5-hydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-7-yl 3,4,5-trihydroxybenzoate

Synonym	Source
tricetiflavan-7-O-gallate	ChEBI

Registry Number	Type	Source
15869677	Reaxys Registry Number	Reaxys

Citation	Type	Source
16724853	PubMed citation	Europe PMC

Last Modified

06 February 2013

General Comment
2013-01-30	The compound is reported to show an optical rotation of [α]²⁰_D−5.3 (c 0.8,MeOH). However the exact stereochemistry (R orS) has not been determined.