CHEBI:65854 - epigallocatechin-(4β→8,2β→O-7)-epicatechin

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ChEBI Name epigallocatechin-(4β→8,2β→O-7)-epicatechin
ChEBI ID CHEBI:65854
ChEBI ASCII Name epigallocatechin-(4beta->8,2beta->O-7)-epicatechin
Definition A proanthocyanidin that is a doubly linked dimer composed of (−)-epicatechin and (−)-epigallocatechin as its flavanol units. Isolated from the wood of Xanthoceras sorbifolium, it exhibits inhibitory activity towards HIV-1 protease.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H24O13
Net Charge 0
Average Mass 592.50380
Monoisotopic Mass 592.122
InChI InChI=1S/C30H24O13/c31-12-6-17(35)23-21(7-12)42-30(11-4-18(36)26(39)19(37)5-11)29(40)25(23)24-22(43-30)9-15(33)13-8-20(38)27(41-28(13)24)10-1-2-14(32)16(34)3-10/h1-7,9,20,25,27,29,31-40H,8H2/t20-,25-,27-,29-,30+/m1/s1
InChIKey WODBGULXKVZGQF-QCPBNORNSA-N
SMILES [H][C@@]1(Oc2c(C[C@H]1O)c(O)cc1O[C@@]3(Oc4cc(O)cc(O)c4[C@@]([H])([C@H]3O)c21)c1cc(O)c(O)c(O)c1)c1ccc(O)c(O)c1
Metabolite of Species Details
Xanthoceras sorbifolium (NCBI:txid99658) Found in xylem (BTO:0001468). Previous component: wood; Methanolic extract of wood 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.
HIV protease inhibitor
An inhibitor of HIV protease, an enzyme required for production of proteins needed for viral assembly.
Application(s): astringent
A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.
(via tannin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing epigallocatechin-(4β→8,2β→O-7)-epicatechin (CHEBI:65854) has functional parent (−)-epicatechin (CHEBI:90)
epigallocatechin-(4β→8,2β→O-7)-epicatechin (CHEBI:65854) has functional parent (−)-epigallocatechin (CHEBI:42255)
epigallocatechin-(4β→8,2β→O-7)-epicatechin (CHEBI:65854) has role HIV protease inhibitor (CHEBI:35660)
epigallocatechin-(4β→8,2β→O-7)-epicatechin (CHEBI:65854) has role metabolite (CHEBI:25212)
epigallocatechin-(4β→8,2β→O-7)-epicatechin (CHEBI:65854) is a proanthocyanidin (CHEBI:26267)
IUPAC Name
(2R,3R,8S,14R,15R)-2-(3,4-dihydroxyphenyl)-8-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H,14H-8,14-methanochromeno[7,8-d][1,3]benzodioxocine-3,5,11,13,15-pentol
Registry Number Type Source
8532288 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
10691716 PubMed citation Europe PMC
Last Modified
21 January 2013