Page last updated: 2024-11-08

egonol

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

Description

egonol : A member of the class of 1-benzofurans that is 1-benzofuran substituted by a methoxy group at position 7, a 1,3-benzodioxol-5-yl group at position 2 and a 3-hydroxypropyl group at position 5. It has been isolated from Styrax agrestis. [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
StyraxgenusA plant genus of the family STYRACACEAE. Sap of these Asian trees are a source of a balsam (BALSAMS). This styrax balsam is 3/4 coniferyl benzoate, 1/8 free BENZOIC ACID, along with benzyl cinnamate, vanillin, and TRITERPENES.[MeSH]StyracaceaeA plant family of the order Ebenales, subclass Dilleniidae, class Magnoliopsida.[MeSH]

Cross-References

ID SourceID
PubMed CID485186
CHEMBL ID470981
CHEBI ID69558
SCHEMBL ID4183989

Synonyms (23)

Synonym
3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propan-1-ol
5-(3''-hydroxypropyl)-7-methoxy-2-(3',4'-methylenedioxyphenyl)benzofuran
3-(2-benzo[1,3]dioxol-5-yl-7-methoxy-benzofuran-5-yl)-propan-1-ol
2-(1,3-benzodioxol-5-yl)-7-methoxy-5-benzofuranpropanol
530-22-3
5-benzofuranpropanol, 2-(1,3-benzodioxol-5-yl)-7-methoxy-
inchi=1/c19h18o5/c1-21-18-8-12(3-2-6-20)7-14-10-16(24-19(14)18)13-4-5-15-17(9-13)23-11-22-15/h4-5,7-10,20h,2-3,6,11h2,1h
egonol
3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-benzofuran-5-yl]propan-1-ol
CHEMBL470981 ,
chebi:69558 ,
3-(2-(benzo[d][1,3]dioxol-5-yl)-7-methoxybenzofuran-5-yl)propan-1-ol
bdbm50327911
5-(3-hydroxypropyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran
SCHEMBL4183989
5-benzofuranpropanol, 7-methoxy-2-[3,4-(methylenedioxy)phenyl]-
VOLZBKQSLGCZGC-UHFFFAOYSA-N
3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]-1-propanol #
3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propan-1-ol
5-(2-hydroxypropyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran
2-(1,3-benzodioxol-5-yl)-7-methoxy-5-benzofuranpropanol, 9ci
Q27137901
DTXSID70967474
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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
1-benzofuransA member of the class of benzofurans consisting of a 1-benzofuran skeleton and its substituted derivatives thereof.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
benzodioxoles
primary alcoholA primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.
[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]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Fatty acid synthaseHomo sapiens (human)IC50 (µMol)91.07000.00772.46245.8000AID517164
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (13)

Processvia Protein(s)Taxonomy
osteoblast differentiationFatty acid synthaseHomo sapiens (human)
glandular epithelial cell developmentFatty acid synthaseHomo sapiens (human)
fatty acid metabolic processFatty acid synthaseHomo sapiens (human)
fatty acid biosynthetic processFatty acid synthaseHomo sapiens (human)
inflammatory responseFatty acid synthaseHomo sapiens (human)
ether lipid biosynthetic processFatty acid synthaseHomo sapiens (human)
neutrophil differentiationFatty acid synthaseHomo sapiens (human)
monocyte differentiationFatty acid synthaseHomo sapiens (human)
mammary gland developmentFatty acid synthaseHomo sapiens (human)
modulation by host of viral processFatty acid synthaseHomo sapiens (human)
cellular response to interleukin-4Fatty acid synthaseHomo sapiens (human)
establishment of endothelial intestinal barrierFatty acid synthaseHomo sapiens (human)
fatty-acyl-CoA biosynthetic processFatty acid synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
RNA bindingFatty acid synthaseHomo sapiens (human)
[acyl-carrier-protein] S-acetyltransferase activityFatty acid synthaseHomo sapiens (human)
[acyl-carrier-protein] S-malonyltransferase activityFatty acid synthaseHomo sapiens (human)
3-oxoacyl-[acyl-carrier-protein] synthase activityFatty acid synthaseHomo sapiens (human)
3-oxoacyl-[acyl-carrier-protein] reductase (NADPH) activityFatty acid synthaseHomo sapiens (human)
(3R)-3-hydroxypalmitoyl-[acyl-carrier-protein] dehydratase activityFatty acid synthaseHomo sapiens (human)
protein bindingFatty acid synthaseHomo sapiens (human)
(3R)-3-hydroxymyristoyl-[acyl-carrier-protein] dehydratase activityFatty acid synthaseHomo sapiens (human)
(3R)-3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase activityFatty acid synthaseHomo sapiens (human)
fatty acyl-[ACP] hydrolase activityFatty acid synthaseHomo sapiens (human)
phosphopantetheine bindingFatty acid synthaseHomo sapiens (human)
cadherin bindingFatty acid synthaseHomo sapiens (human)
(3R)-3-hydroxybutanoyl-[acyl-carrier-protein] hydratase activityFatty acid synthaseHomo sapiens (human)
(3R)-3-hydroxyoctanoyl-[acyl-carrier-protein] dehydratase activityFatty acid synthaseHomo sapiens (human)
enoyl-[acyl-carrier-protein] reductase (NADPH) activityFatty acid synthaseHomo sapiens (human)
fatty acid synthase activityFatty acid synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
Golgi apparatusFatty acid synthaseHomo sapiens (human)
cytosolFatty acid synthaseHomo sapiens (human)
plasma membraneFatty acid synthaseHomo sapiens (human)
membraneFatty acid synthaseHomo sapiens (human)
melanosomeFatty acid synthaseHomo sapiens (human)
glycogen granuleFatty acid synthaseHomo sapiens (human)
extracellular exosomeFatty acid synthaseHomo sapiens (human)
cytoplasmFatty acid synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID382878Antibacterial activity against Bacillus subtilis by Muller Hilton broth method2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and antibacterial activity of egonol derivatives.
AID1498471Cytotoxicity against human CEM/ADR5000 cells over-expressing P-gp assessed as reduction in cell viability after 72 hrs by resazurin dye based assay2018Bioorganic & medicinal chemistry, 07-23, Volume: 26, Issue:12
Access to new highly potent antileukemia, antiviral and antimalarial agents via hybridization of natural products (homo)egonol, thymoquinone and artemisinin.
AID1324362Cytotoxicity against aromatase overexpressing HEK293A cells assessed as effect on cell proliferation at 10 to 50 uM2016Bioorganic & medicinal chemistry letters, 11-15, Volume: 26, Issue:22
2-Phenylbenzo[b]furans: Synthesis and promoting activity on estrogen biosynthesis.
AID1076686Cytotoxicity against human multidrug-resistant CEM/ADR5000 cells expressing p-glycoprotein by resazurin assay2014European journal of medicinal chemistry, Mar-21, Volume: 75Synthesis and study of cytotoxic activity of 1,2,4-trioxane- and egonol-derived hybrid molecules against Plasmodium falciparum and multidrug-resistant human leukemia cells.
AID568137Antimicrobial activity against Staphylococcus aureus ATCC 29213 by MHB method2011Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3
Synthesis of egonol derivatives and their antimicrobial activities.
AID1256625Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production at 3 to 30 ug/ml after 24 hrs by Griess reaction2015Bioorganic & medicinal chemistry letters, Nov-15, Volume: 25, Issue:22
Inhibitory effects of compounds from Styrax obassia on NO production.
AID399902Cytotoxicity against human KATO III cells2004Journal of natural products, Feb, Volume: 67, Issue:2
Biologically active compounds from Aphyllophorales (polypore) fungi.
AID1076689Antimalarial activity against Plasmodium falciparum 3D7 assessed as growth inhibition after 3 days by HRP2 based ELISA2014European journal of medicinal chemistry, Mar-21, Volume: 75Synthesis and study of cytotoxic activity of 1,2,4-trioxane- and egonol-derived hybrid molecules against Plasmodium falciparum and multidrug-resistant human leukemia cells.
AID382879Antibacterial activity against Candida albicans by Muller Hilton broth method2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and antibacterial activity of egonol derivatives.
AID1498470Cytotoxicity against human CCRF-CEM cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay2018Bioorganic & medicinal chemistry, 07-23, Volume: 26, Issue:12
Access to new highly potent antileukemia, antiviral and antimalarial agents via hybridization of natural products (homo)egonol, thymoquinone and artemisinin.
AID1076685Resistance ratio of IC50 for human multidrug-resistant CEM/ADR5000 cells expressing p-glycoprotein to IC50 for human CCRF-CEM cells2014European journal of medicinal chemistry, Mar-21, Volume: 75Synthesis and study of cytotoxic activity of 1,2,4-trioxane- and egonol-derived hybrid molecules against Plasmodium falciparum and multidrug-resistant human leukemia cells.
AID568139Antimicrobial activity against Candida albicans ATCC 10231 by MHB method2011Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3
Synthesis of egonol derivatives and their antimicrobial activities.
AID623717Inhibition of electric eel AChE using acetylthiocholine iodide as substrate by spectrophotometric method2011Journal of natural products, Oct-28, Volume: 74, Issue:10
Benzofurans from Styrax agrestis as acetylcholinesterase inhibitors: structure-activity relationships and molecular modeling studies.
AID1498473Antiviral activity against GFP-fused Human cytomegalovirus AD169 infected in primary HFF2018Bioorganic & medicinal chemistry, 07-23, Volume: 26, Issue:12
Access to new highly potent antileukemia, antiviral and antimalarial agents via hybridization of natural products (homo)egonol, thymoquinone and artemisinin.
AID517164Inhibition of FAS2010Bioorganic & medicinal chemistry letters, Oct-15, Volume: 20, Issue:20
Fatty acid synthase inhibitors of phenolic constituents isolated from Garcinia mangostana.
AID382880Antibacterial activity against Escherichia coli by Muller Hilton broth method2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and antibacterial activity of egonol derivatives.
AID568140Antimicrobial activity against Escherichia coli ATCC 8739 by MHB method2011Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3
Synthesis of egonol derivatives and their antimicrobial activities.
AID382877Antibacterial activity against Staphylococcus aureus by Muller Hilton broth method2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and antibacterial activity of egonol derivatives.
AID1076688Cytotoxicity against human CCRF-CEM cells by resazurin assay2014European journal of medicinal chemistry, Mar-21, Volume: 75Synthesis and study of cytotoxic activity of 1,2,4-trioxane- and egonol-derived hybrid molecules against Plasmodium falciparum and multidrug-resistant human leukemia cells.
AID623718Inhibition of human recombinant AChE using acetylthiocholine iodide as substrate by spectrophotometric method2011Journal of natural products, Oct-28, Volume: 74, Issue:10
Benzofurans from Styrax agrestis as acetylcholinesterase inhibitors: structure-activity relationships and molecular modeling studies.
AID623719Inhibition of human serum BChE using butyrylthiocholine iodide as substrate by spectrophotometric method2011Journal of natural products, Oct-28, Volume: 74, Issue:10
Benzofurans from Styrax agrestis as acetylcholinesterase inhibitors: structure-activity relationships and molecular modeling studies.
AID1498472Antimalarial activity against Plasmodium falciparum 3D7 infected in human erythrocytes after 72 hrs by SYBR green dye fluorescence assay2018Bioorganic & medicinal chemistry, 07-23, Volume: 26, Issue:12
Access to new highly potent antileukemia, antiviral and antimalarial agents via hybridization of natural products (homo)egonol, thymoquinone and artemisinin.
AID568138Antimicrobial activity against Bacillus subtilis ATCC 6633 by MHB method2011Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3
Synthesis of egonol derivatives and their antimicrobial activities.
AID623720Inhibition of human recombinant AChE-mediated amyloid beta (1-40) aggregation at 100 uM after 48 hrs by thioflavin T fluorescence assay2011Journal of natural products, Oct-28, Volume: 74, Issue:10
Benzofurans from Styrax agrestis as acetylcholinesterase inhibitors: structure-activity relationships and molecular modeling studies.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (22.22)29.6817
2010's7 (77.78)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (11.11%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (88.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]