Page last updated: 2024-11-08

eugeniin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

eugeniin: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

eugeniin : An ellagitannin isolated from the dried flower buds of Eugenia caryophyllata. It exhibits alpha-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. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

FloraRankFlora DefinitionFamilyFamily Definition
EugeniagenusA genus in the family Myrtaceae sometimes known as stoppers in FOLK MEDICINE. Many species of the genus SYZYGIUM have synonymous names that begin with the Eugenia genus name.[MeSH]MyrtaceaeThe myrtle plant family of the order Myrtales. It includes several aromatic medicinal plants such as EUCALYPTUS.[MeSH]

Cross-References

ID SourceID
PubMed CID442679
CHEMBL ID450745
CHEBI ID4916
SCHEMBL ID618554
MeSH IDM0286782

Synonyms (15)

Synonym
MEGXP0_001162
ACON1_001321
NCGC00180631-01
58970-75-5
eugeniin
cornustannin 2
bdbm50250989
chebi:4916 ,
CHEMBL450745 ,
(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)
1,2,3-trigalloyl-4,6-hexahydroxydiphenoyl beta-d-glucopyranose
beta-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)
SCHEMBL618554
Q7697608
[(10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis[(3,4,5-trihydroxybenzoyl)oxy]-9,14,17-trioxatetracyclo[17.4.0.02,7.010,15]tricosa-1(23),2,4,6,19,21-hexaen-11-yl] 3,4,5-trihydroxybenzoate

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Thus, the therapeutic efficacy of oral administration at the various doses of eugeniin was similar to that of intraperitoneal administration, suggesting that the oral bioavailability of eugeniin was high with respect to absorption."( Biological characterization of eugeniin as an anti-herpes simplex virus type 1 compound in vitro and in vivo.
Hozumi, T; Kadota, S; Kurokawa, M; Namba, T; Shiraki, K; Tsurita, M, 2001
)
0.82
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antifungal agentAn antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
anti-HSV-1 agentAn anti-HSV agent agent that destroys or inhibits the replication of herpes simplex virus-1.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
EC 3.2.1.20 (alpha-glucosidase) inhibitorAn EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-glucosidase (EC 3.2.1.20).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
lactoneAny cyclic carboxylic ester containing a 1-oxacycloalkan-2-one structure, or an analogue having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.
beta-D-glucosideAny D-glucoside in which the anomeric centre has beta-configuration.
ellagitanninA form of hydrolysable tannin produced from ellagic acid. Ellagitannins are glucosides which are readily hydrolysed by water to regenerate ellagic acid when the plants are eaten.
gallate esterA benzoate ester that is any ester resulting from the formal condensation of the carboxy group of gallic acid (3,4,5-trihydroxybenzoic acid) with an alcoholic or phenolic hydroxy group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
superpathway of hydrolyzable tannin biosynthesis023
cornusiin E biosynthesis013
cornusiin E biosynthesis014
superpathway of hydrolyzable tannin biosynthesis030

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Squalene monooxygenase Rattus norvegicus (Norway rat)IC50 (µMol)1.60000.06102.344610.0000AID357307
Beta-secretase 1Homo sapiens (human)IC50 (µMol)3.10000.00061.619410.0000AID1153318
Beta-secretase 1Homo sapiens (human)Ki6.84000.00031.35248.0000AID1153318
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
proteolysisBeta-secretase 1Homo sapiens (human)
membrane protein ectodomain proteolysisBeta-secretase 1Homo sapiens (human)
response to lead ionBeta-secretase 1Homo sapiens (human)
protein processingBeta-secretase 1Homo sapiens (human)
amyloid-beta formationBeta-secretase 1Homo sapiens (human)
amyloid precursor protein catabolic processBeta-secretase 1Homo sapiens (human)
positive regulation of neuron apoptotic processBeta-secretase 1Homo sapiens (human)
amyloid-beta metabolic processBeta-secretase 1Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of painBeta-secretase 1Homo sapiens (human)
prepulse inhibitionBeta-secretase 1Homo sapiens (human)
cellular response to copper ionBeta-secretase 1Homo sapiens (human)
cellular response to manganese ionBeta-secretase 1Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionBeta-secretase 1Homo sapiens (human)
signaling receptor ligand precursor processingBeta-secretase 1Homo sapiens (human)
cellular response to amyloid-betaBeta-secretase 1Homo sapiens (human)
amyloid fibril formationBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
amyloid-beta bindingBeta-secretase 1Homo sapiens (human)
endopeptidase activityBeta-secretase 1Homo sapiens (human)
aspartic-type endopeptidase activityBeta-secretase 1Homo sapiens (human)
protein bindingBeta-secretase 1Homo sapiens (human)
peptidase activityBeta-secretase 1Homo sapiens (human)
beta-aspartyl-peptidase activityBeta-secretase 1Homo sapiens (human)
enzyme bindingBeta-secretase 1Homo sapiens (human)
protein serine/threonine kinase bindingBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (20)

Processvia Protein(s)Taxonomy
lysosomeBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
early endosomeBeta-secretase 1Homo sapiens (human)
late endosomeBeta-secretase 1Homo sapiens (human)
multivesicular bodyBeta-secretase 1Homo sapiens (human)
endoplasmic reticulum lumenBeta-secretase 1Homo sapiens (human)
Golgi apparatusBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
synaptic vesicleBeta-secretase 1Homo sapiens (human)
cell surfaceBeta-secretase 1Homo sapiens (human)
endosome membraneBeta-secretase 1Homo sapiens (human)
membraneBeta-secretase 1Homo sapiens (human)
axonBeta-secretase 1Homo sapiens (human)
dendriteBeta-secretase 1Homo sapiens (human)
neuronal cell bodyBeta-secretase 1Homo sapiens (human)
membrane raftBeta-secretase 1Homo sapiens (human)
recycling endosomeBeta-secretase 1Homo sapiens (human)
Golgi-associated vesicle lumenBeta-secretase 1Homo sapiens (human)
hippocampal mossy fiber to CA3 synapseBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID465730Antiviral activity against E1 and E2 envelope protein expressing HCV infected in HepG2 cells assessed as inhibition of viral invasion at 1 uM after 24 hrs by SEAP reporter gene assay2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos.
AID1153318Inhibition of BACE1 (unknown origin)2014Bioorganic & medicinal chemistry letters, Jul-01, Volume: 24, Issue:13
β-Secretase (BACE1)-inhibiting C-methylrotenoids from Abronia nana suspension cultures.
AID358168Cytotoxicity against human HCT8 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID358165Cytotoxicity against human PRMI7951 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID465728Antiviral activity against E1 and E2 envelope protein expressing HCV infected in HepG2 cells assessed as inhibition of viral invasion at 10 uM after 24 hrs by SEAP reporter gene assay2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos.
AID358166Cytotoxicity against human KB cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID358169Cytotoxicity against human TE671 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID357307Inhibition of C-terminal hexahistidine-tagged rat recombinant squalene epoxidase without N-terminal putative membrane domain expressed in Escherichia coli2001Journal of natural products, Aug, Volume: 64, Issue:8
Ellagitannins and hexahydroxydiphenoyl esters as inhibitors of vertebrate squalene epoxidase.
AID465731Antiviral activity against G envelope protein expressing HCV infected in HepG2 cells assessed as inhibition of viral invasion at 10 uM after 24 hrs by SEAP reporter gene assay2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos.
AID465732Antiviral activity against G envelope protein expressing HCV infected in HepG2 cells assessed as inhibition of viral invasion at 3 uM after 24 hrs by SEAP reporter gene assay2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos.
AID465733Antiviral activity against G envelope protein expressing HCV infected in HepG2 cells assessed as inhibition of viral invasion at 1 uM after 24 hrs by SEAP reporter gene assay2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos.
AID465729Antiviral activity against E1 and E2 envelope protein expressing HCV infected in HepG2 cells assessed as inhibition of viral invasion at 3 uM after 24 hrs by SEAP reporter gene assay2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos.
AID358167Cytotoxicity against human A549 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (23.08)18.2507
2000's7 (53.85)29.6817
2010's2 (15.38)24.3611
2020's1 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.73

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index23.73 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.73)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (7.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (92.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]