CHEBI:4916 - eugeniin

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ChEBI Name eugeniin
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:65872
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Formula C41H30O26
Net Charge 0
Average Mass 938.66130
Monoisotopic Mass 938.103
InChI InChI=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
SMILES Oc1cc(cc(O)c1O)C(=O)O[C@@H]1O[C@@H]2COC(=O)c3cc(O)c(O)c(O)c3-c3c(O)c(O)c(O)cc3C(=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
Metabolite of Species Details
Eugenia caryophyllata (IPNI:593931-1) Found in flower bud (BTO:0000470). Dried flower bud See: PubMed
Roles Classification
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
anti-HSV-1 agent
An anti-HSV agent agent that destroys or inhibits the replication of herpes simplex virus-1.
EC (alpha-glucosidase) inhibitor
An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-glucosidase (EC
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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 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 (α-glucosidase) inhibitor (CHEBI:67239)
eugeniin (CHEBI:4916) has role metabolite (CHEBI:25212)
eugeniin (CHEBI:4916) is a β-D-glucoside (CHEBI:22798)
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)
(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 Sources
1,2,3-trigalloyl-4,6-hexahydroxydiphenoyl β-D-glucopyranose ChEBI
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
Cornustannin 2 HMDB
Tellimagrandin II KEGG COMPOUND
Manual Xrefs Databases
C00002920 KNApSAcK
HMDB0039265 HMDB
Tellimagrandin_II Wikipedia
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Registry Numbers Types Sources
58970-75-5 CAS Registry Number KEGG COMPOUND
9038164 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10737184 PubMed citation Europe PMC
11259565 PubMed citation Europe PMC
14599517 PubMed citation Europe PMC
20922478 PubMed citation Europe PMC
8476228 PubMed citation Europe PMC
Last Modified
28 July 2014