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CHEBI:4916 - eugeniin

ChEBI IDCHEBI:4916
ChEBI Nameeugeniin
Stars
DefinitionAn ellagitannin isolated from the dried flower buds of Eugenia caryophyllata. It exhibits α-glucosidase inhibitory activity and antiviral activity against acyclovir and phosphonoacetic acid (PAA)-resistant herpes simplex virus type 1 (HSV-1) as well as the wild-type HSV-1.
Secondary ChEBI IDCHEBI:65872
Last Modified14 March 2025
DownloadsMolfile
FormulaC41H30O26
Net Charge0
Average Mass938.665
Monoisotopic Mass938.10253
SMILESO=C(O[C@@H]1O[C@@H]2COC(=O)c3cc(O)c(O)c(O)c3-c3c(cc(O)c(O)c3O)C(=O)O[C@H]2[C@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@H]1OC(=O)c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1
InChIInChI=1S/C41H30O26/c42-15-1-10(2-16(43)26(15)50)36(57)65-34-33-23(9-62-39(60)13-7-21(48)29(53)31(55)24(13)25-14(40(61)64-33)8-22(49)30(54)32(25)56)63-41(67-38(59)12-5-19(46)28(52)20(47)6-12)35(34)66-37(58)11-3-17(44)27(51)18(45)4-11/h1-8,23,33-35,41-56H,9H2/t23-,33-,34+,35-,41+/m1/s1
InChIKeyJCGHAEBIBSEQAD-UUUCSUBKSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Eugenia caryophyllata (IPNI:593931-1) flower bud (BTO:0000470) PubMed (10737184) Dried flower bud
Roles Classification
Biological Roles:
anti-HSV-1 agent  An anti-HSV agent agent that destroys or inhibits the replication of herpes simplex virus-1.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
EC 3.2.1.20 (alpha-glucosidase) inhibitor  An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of α-glucosidase (EC 3.2.1.20).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
astringent  A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.
ChEBI Ontology
Outgoing Relation(s)
eugeniin (CHEBI:4916) has functional parent gallic acid (CHEBI:30778)
eugeniin (CHEBI:4916) has role anti-HSV-1 agent (CHEBI:64953)
eugeniin (CHEBI:4916) has role antifungal agent (CHEBI:35718)
eugeniin (CHEBI:4916) has role antineoplastic agent (CHEBI:35610)
eugeniin (CHEBI:4916) has role EC 3.2.1.20 (α-glucosidase) inhibitor (CHEBI:67239)
eugeniin (CHEBI:4916) has role metabolite (CHEBI:25212)
eugeniin (CHEBI:4916) is a ellagitannin (CHEBI:23909)
eugeniin (CHEBI:4916) is a gallate ester (CHEBI:37576)
eugeniin (CHEBI:4916) is a lactone (CHEBI:25000)
eugeniin (CHEBI:4916) is a β-D-glucoside (CHEBI:22798)
eugeniin (CHEBI:4916) is conjugate acid of tellimagrandin II(2−) (CHEBI:145905)
Incoming Relation(s)
tellimagrandin II(2−) (CHEBI:145905) is conjugate base of eugeniin (CHEBI:4916)
IUPAC Name 
(11aR,13S,14R,15S,15aR)-2,3,4,5,6,7-hexahydroxy-9,17-dioxo-9,11,11a,13,14,15,15a,17-octahydrodibenzo[g,i]pyrano[3,2-b][1,5]dioxacycloundecine-13,14,15-triyl tris(3,4,5-trihydroxybenzoate)
Synonyms  Source
EugeniinKEGG COMPOUND
Tellimagrandin IIKEGG COMPOUND
β-D-Glucopyranose,cyclic4,6-(4,4',5,5',6,6'-hexahydroxy(1,1'-biphenyl)-2,2'-dicarboxylate)1,2,3-tris(3,4,5-trihydroxybenzoate)ChemIDplus
1,2,3-trigalloyl-4,6-hexahydroxydiphenoyl β-D-glucopyranoseChEBI
Cornustannin 2HMDB
Manual XrefsDatabases
C10224KEGG COMPOUND
Tellimagrandin_IIWikipedia
HMDB0039265HMDB
C00002920KNApSAcK
CPD-8949MetaCyc
Registry NumbersSources
Reaxys:9038164Reaxys
CAS:58970-75-5KEGG COMPOUND
Citations