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

ChEBI IDCHEBI:65854
ChEBI Nameepigallocatechin-(4β→8,2β→O-7)-epicatechin
Stars
ASCII Nameepigallocatechin-(4beta->8,2beta->O-7)-epicatechin
DefinitionA 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.
Last Modified21 January 2013
DownloadsMolfile
FormulaC30H24O13
Net Charge0
Average Mass592.509
Monoisotopic Mass592.12169
SMILES[H][C@@]12c3c(O)cc(O)cc3O[C@@](c3cc(O)c(O)c(O)c3)(Oc3cc(O)c4c(c31)O[C@]([H])(c1ccc(O)c(O)c1)[C@H](O)C4)[C@@H]2O
InChIInChI=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
InChIKeyWODBGULXKVZGQF-QCPBNORNSA-N
Species of MetaboliteComponentSourceComments
Xanthoceras sorbifolium (ncbitaxon:99658) xylem (BTO:0001468) PubMed (10691716) Previous component: wood; Methanolic extract of wood
Roles Classification
Biological Roles:
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:
astringent  A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:8532288Reaxys
Citations