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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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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).
anti-HSV-1 agent  An anti-HSV agent agent that destroys or inhibits the replication of herpes simplex virus-1.
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