Page last updated: 2024-12-10

bilobol

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

Description

bilobol: structure given in first source; RN given refers to (Z)-isomer; RN for cpd without isomeric designation not avail 6/90 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5281852
CHEMBL ID461628
CHEBI ID3104
SCHEMBL ID164545
MeSH IDM0176486

Synonyms (34)

Synonym
CHEBI:3104 ,
5-[(8z)-pentadec-8-enyl]resorcinol
bilobol
22910-86-7
5-[(8z)-pentadec-8-en-1-yl]benzene-1,3-diol
5-(8'z-heptadecenyl)resorcinol
5-[(z)-pentadec-8-enyl]benzene-1,3-diol
bdbm50241751
CHEMBL461628 ,
5-[8'(z)-pentadecenyl]resorcinol
5-{8(z),-pentadecenyl}resorcinol
1,3-benzenediol, 5-(8-pentadecenyl)-, (z)-
5-[(z)-pentadec-8-enylo]resorcinol
SCHEMBL164545
trifurcatol a2
cardol monoene
bilobol c15:1
5-(8z-pentadecenyl)resorcinol
1,3-benzenediol, 5-(8z)-8-pentadecenyl-
(z)-5-(pentadec-8-en-1-yl)benzene-1,3-diol
21:1-.omega.7-cardol
TUGAUFMQYWZJAB-FPLPWBNLSA-N
5-[(z)-pentadec-8-enyl]resorcinol
resorcinol, 5-(8-pentadecenyl)-, (z)-
cis-5-n-pentadec-8'-enylresorcino
LMPK15030001
DTXSID90872874
cardol c15:1
Q4913564
PD182474
1,3-benzenediol, 5-[(8z)-8-pentadecen-1-yl]-
5-(8z)-8-pentadecenyl-1,3-benzenediol
cis-5-pentadec-8'-enylresorcinol
AKOS040735273

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" As constituents with potential contact allergenic and toxic properties in crude Ginkgo extracts a group of alkylphenols (e."( Evidence for toxic effects of alkylphenols from Ginkgo biloba in the hen's egg test (HET).
Baron-Ruppert, G; Luepke, NP, 2001
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
5-alkenylresorcinolA resorcinol compound having an alkenyl substituent at the 5-position.
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)IC50 (µMol)30.03005.66005.66005.6600AID401415
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (7)

Processvia Protein(s)Taxonomy
in utero embryonic development1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
epidermal growth factor receptor signaling pathway1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
phospholipid catabolic process1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
positive regulation of epithelial cell migration1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
cellular response to vascular endothelial growth factor stimulus1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
phosphatidylinositol metabolic process1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
cellular response to epidermal growth factor stimulus1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
phosphatidylinositol phospholipase C activity1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
guanyl-nucleotide exchange factor activity1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
calcium ion binding1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
protein binding1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
calcium-dependent phospholipase C activity1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
plasma membrane1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
ruffle1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
cytoplasm1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
lamellipodium1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
COP9 signalosome1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (43)

Assay IDTitleYearJournalArticle
AID335795Antibacterial activity against Bacillus circulans at 100 ug/disk after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID335805Antibacterial activity against Pseudomonas fluorescens N5 after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID376624Antimicrobial activity against methicillin-resistant Staphylococcus aureus ATCC 43300 by antimicrobial susceptibility test2006Journal of natural products, Apr, Volume: 69, Issue:4
5-alkylresorcinols from Merulius incarnatus.
AID335810Antifungal activity against Saccharomyces cerevisiae X-3 after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID379522Inhibition of thrombin at 50 uM2006Journal of natural products, Nov, Volume: 69, Issue:11
A nitrogen-containing 3-alkyl-1,4-benzoquinone and a gomphilactone derivative from Embelia ribes.
AID335803Antibacterial activity against Escherichia coli U9 after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID332456Inhibition of mushroom tyrosinase assessed as oxidation of L-DOPA1994Journal of natural products, Apr, Volume: 57, Issue:4
Tyrosinase inhibitors from Anacardium occidentale fruits.
AID335811Antifungal activity against Aspergillus niger ATCC 9142 after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID401419Growth inhibition of human MCF7 cells after 2 days by SRB assay1998Journal of natural products, Jul, Volume: 61, Issue:7
Phospholipase Cgamma1 inhibitory principles from the sarcotestas of Ginkgo biloba.
AID335807Antibacterial activity against Salmonella after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID401422Growth inhibition of human HT1197 cells after 2 days by SRB assay1998Journal of natural products, Jul, Volume: 61, Issue:7
Phospholipase Cgamma1 inhibitory principles from the sarcotestas of Ginkgo biloba.
AID335814Antifungal activity against Gibberella fujikuroi IMI 58289 after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID335809Antifungal activity against Saccharomyces cerevisiae K-2 after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID335794Antibacterial activity against Bacillus circulans at 200 ug/disk after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID401420Growth inhibition of human HCT15 cells after 2 days by SRB assay1998Journal of natural products, Jul, Volume: 61, Issue:7
Phospholipase Cgamma1 inhibitory principles from the sarcotestas of Ginkgo biloba.
AID335815Antifungal activity against Mucor mucedo after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID335797Antibacterial activity against Bacillus licheniformis CECT20 at 100 ug/disk after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID379517Cytotoxicity against human A2780 cells after 96 hrs by MTT assay2006Journal of natural products, Nov, Volume: 69, Issue:11
A nitrogen-containing 3-alkyl-1,4-benzoquinone and a gomphilactone derivative from Embelia ribes.
AID335799Antibacterial activity against Enterococcus faecalis S-86 at 100 ug/disk after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID335800Antibacterial activity against Micrococcus lysodeikticus at 200 ug/disk after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID335812Antifungal activity against Botrytis cinerea CECT 2100 after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID335798Antibacterial activity against Enterococcus faecalis S-86 at 200 ug/disk after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID335802Antibacterial activity against Alcaligenes faecalis after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID379520Cytotoxicity against human HCT8 cells after 96 hrs by MTT assay2006Journal of natural products, Nov, Volume: 69, Issue:11
A nitrogen-containing 3-alkyl-1,4-benzoquinone and a gomphilactone derivative from Embelia ribes.
AID401423Growth inhibition of human CCD-18Co cells after 2 days by SRB assay1998Journal of natural products, Jul, Volume: 61, Issue:7
Phospholipase Cgamma1 inhibitory principles from the sarcotestas of Ginkgo biloba.
AID379521Inhibition of PTP1B at 50 uM2006Journal of natural products, Nov, Volume: 69, Issue:11
A nitrogen-containing 3-alkyl-1,4-benzoquinone and a gomphilactone derivative from Embelia ribes.
AID335792Antibacterial activity against Bacillus subtilis CECT 397 at 200 ug/disk after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID335791Antibacterial activity against Bacillus megaterium at 100 ug/disk after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID379516Cytotoxicity against human A549 cells after 96 hrs by MTT assay2006Journal of natural products, Nov, Volume: 69, Issue:11
A nitrogen-containing 3-alkyl-1,4-benzoquinone and a gomphilactone derivative from Embelia ribes.
AID332455Inhibition of mushroom tyrosinase assessed as oxidation of L-DOPA at 0.8 mM1994Journal of natural products, Apr, Volume: 57, Issue:4
Tyrosinase inhibitors from Anacardium occidentale fruits.
AID335813Antifungal activity against Botrytis cinerea CECT 2850 after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID335804Antibacterial activity against Pseudomonas reptilovora after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID379518Cytotoxicity against human Bel-7402 cells after 96 hrs by MTT assay2006Journal of natural products, Nov, Volume: 69, Issue:11
A nitrogen-containing 3-alkyl-1,4-benzoquinone and a gomphilactone derivative from Embelia ribes.
AID379519Cytotoxicity against human BGC-823 cells after 96 hrs by MTT assay2006Journal of natural products, Nov, Volume: 69, Issue:11
A nitrogen-containing 3-alkyl-1,4-benzoquinone and a gomphilactone derivative from Embelia ribes.
AID335790Antibacterial activity against Bacillus megaterium at 200 ug/disk after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID401418Growth inhibition of human A549 cells after 2 days by SRB assay1998Journal of natural products, Jul, Volume: 61, Issue:7
Phospholipase Cgamma1 inhibitory principles from the sarcotestas of Ginkgo biloba.
AID401415Inhibition of bovine brain PI-PLCgamma11998Journal of natural products, Jul, Volume: 61, Issue:7
Phospholipase Cgamma1 inhibitory principles from the sarcotestas of Ginkgo biloba.
AID335806Antibacterial activity against Proteus after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID335808Antifungal activity against Saccharomyces cerevisiae S1 after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID401421Growth inhibition of human SKOV3 cells after 2 days by SRB assay1998Journal of natural products, Jul, Volume: 61, Issue:7
Phospholipase Cgamma1 inhibitory principles from the sarcotestas of Ginkgo biloba.
AID335796Antibacterial activity against Bacillus licheniformis CECT20 at 200 ug/disk after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID335793Antibacterial activity against Bacillus subtilis CECT 397 at 100 ug/disk after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
AID335801Antibacterial activity against Staphylococcus aureus ATCC 8 at 200 ug/disk after 18 hrs by disk diffusion assay1993Journal of natural products, Oct, Volume: 56, Issue:10
Use of alkenylresorcinols from Ononis speciosa as synthetic precursors of compounds with potential biological activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (33.33)18.2507
2000's3 (25.00)29.6817
2010's3 (25.00)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.56

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 Index22.56 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.68 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index3.00 (0.95)

This Compound (22.56)

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]