Page last updated: 2024-11-13

debromoaplysiatoxin

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

Description

debromoaplysiatoxin: sea algae toxin from lyngbya majuscula.; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

debromoaplysiatoxin : A member of the class of aplysiatoxins that has the structure of the parent aplysiatoxin, but is lacking the bromo substituent on the benzene ring at the position para to the phenolic hydroxy group. It is a cyanotoxin produced by several species of freshwater and marine cyanobacteria, as well as algae and molluscs. [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]

Cross-References

ID SourceID
PubMed CID44276054
CHEMBL ID282159
CHEBI ID4344
MeSH IDM0067735

Synonyms (10)

Synonym
(1s,3r,4s,9r,13s,14r)-13-hydroxy-9-((r)-1-hydroxy-ethyl)-3-[(1s,4s)-4-(3-hydroxy-phenyl)-4-methoxy-1-methyl-butyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxa-tricyclo[11.3.1.1*1,5*]octadecane-7,11-dione
bdbm50041401
debromoaplysiatoxin
52423-28-6
chebi:4344 ,
CHEMBL282159 ,
(1s,3r,4s,9r,13s,14r)-13-hydroxy-9-[(1r)-1-hydroxyethyl]-3-[(2s,5s)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1(1,5)]octadecane-7,11-dione
17-debromoaplysiatoxin
DTXSID80880084
Q23718672

Research Excerpts

Overview

Debromoaplysiatoxin (DAT) is a tumor promoter isolated from sea hare. exhibits anti-proliferative activity against several cancer cell lines.

ExcerptReferenceRelevance
"Debromoaplysiatoxin (DAT) is a tumor promoter isolated from sea hare and exhibits anti-proliferative activity against several cancer cell lines. "( Effects of the methoxy group in the side chain of debromoaplysiatoxin on its tumor-promoting and anti-proliferative activities.
Irie, K; Kamachi, H; Kikumori, M; Nagai, H; Suenaga, K; Suzuki, N; Tokuda, H; Yanagita, RC, 2013
)
2.09

Dosage Studied

ExcerptRelevanceReference
" The dose-response curves for the binding of [3H]lyngbyatoxin A and [3H]debromoaplysiatoxin to a mouse epidermal particulate fraction are virtually the same as the one previously described for [3H]12-O-tetradecanoylphorbol-13-acetate ([3H]TPA)."( Binding studies of [3H]lyngbyatoxin A and [3H]debromoaplysiatoxin to the phorbol ester receptor in a mouse epidermal particulate fraction.
Entzeroth, M; Fujiki, H; Hakii, H; Moore, RE; Morimoto, H; Patterson, GM; Suganuma, M; Sugimura, T, 1986
)
0.76
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
cyanotoxinAny toxin produced by cyanobacteria (blue-green algae).
algal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
carcinogenic agentA role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
marine metaboliteAny metabolite produced during a metabolic reaction in marine macro- and microorganisms.
protein kinase C agonistAn agonist that selectively binds to and activates a protein kinase C receptor
[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 (7)

ClassDescription
aplysiatoxinsA class of macrodiolides that consists of aplysiatoxin and its structural analogues.
cyclic hemiketalA hemiacetal having the structure R2C(OH)OR (R =/= H), derived from a ketone by formal addition of an alcohol to the carbonyl group. The term 'cyclic hemiketals', once abandoned by IUPAC, has been reinstated as a subclass of hemiacetals.
etherAn organooxygen compound with formula ROR, where R is not hydrogen.
secondary alcoholA secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
organic heterotricyclic compoundAn organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms.
spiroketalA cyclic ketal in which the ketal carbon is the only common atom of two rings.
[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)
Protein kinase C alpha typeHomo sapiens (human)Ki0.02000.00021.09456.9600AID164964
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (31)

Processvia Protein(s)Taxonomy
angiogenesisProtein kinase C alpha typeHomo sapiens (human)
positive regulation of endothelial cell proliferationProtein kinase C alpha typeHomo sapiens (human)
desmosome assemblyProtein kinase C alpha typeHomo sapiens (human)
chromatin remodelingProtein kinase C alpha typeHomo sapiens (human)
protein phosphorylationProtein kinase C alpha typeHomo sapiens (human)
mitotic nuclear membrane disassemblyProtein kinase C alpha typeHomo sapiens (human)
cell adhesionProtein kinase C alpha typeHomo sapiens (human)
positive regulation of endothelial cell migrationProtein kinase C alpha typeHomo sapiens (human)
positive regulation of cardiac muscle hypertrophyProtein kinase C alpha typeHomo sapiens (human)
peptidyl-serine phosphorylationProtein kinase C alpha typeHomo sapiens (human)
peptidyl-threonine phosphorylationProtein kinase C alpha typeHomo sapiens (human)
positive regulation of cell migrationProtein kinase C alpha typeHomo sapiens (human)
positive regulation of lipopolysaccharide-mediated signaling pathwayProtein kinase C alpha typeHomo sapiens (human)
negative regulation of glial cell apoptotic processProtein kinase C alpha typeHomo sapiens (human)
regulation of mRNA stabilityProtein kinase C alpha typeHomo sapiens (human)
positive regulation of blood vessel endothelial cell migrationProtein kinase C alpha typeHomo sapiens (human)
post-translational protein modificationProtein kinase C alpha typeHomo sapiens (human)
positive regulation of macrophage differentiationProtein kinase C alpha typeHomo sapiens (human)
positive regulation of angiogenesisProtein kinase C alpha typeHomo sapiens (human)
positive regulation of bone resorptionProtein kinase C alpha typeHomo sapiens (human)
positive regulation of cell adhesionProtein kinase C alpha typeHomo sapiens (human)
positive regulation of mitotic cell cycleProtein kinase C alpha typeHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeProtein kinase C alpha typeHomo sapiens (human)
response to interleukin-1Protein kinase C alpha typeHomo sapiens (human)
regulation of platelet aggregationProtein kinase C alpha typeHomo sapiens (human)
apoptotic signaling pathwayProtein kinase C alpha typeHomo sapiens (human)
positive regulation of adenylate cyclase-activating G protein-coupled receptor signaling pathwayProtein kinase C alpha typeHomo sapiens (human)
positive regulation of angiotensin-activated signaling pathwayProtein kinase C alpha typeHomo sapiens (human)
positive regulation of dense core granule biogenesisProtein kinase C alpha typeHomo sapiens (human)
intracellular signal transductionProtein kinase C alpha typeHomo sapiens (human)
positive regulation of insulin secretionProtein kinase C alpha typeHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
protein kinase activityProtein kinase C alpha typeHomo sapiens (human)
diacylglycerol-dependent serine/threonine kinase activityProtein kinase C alpha typeHomo sapiens (human)
calcium,diacylglycerol-dependent serine/threonine kinase activityProtein kinase C alpha typeHomo sapiens (human)
integrin bindingProtein kinase C alpha typeHomo sapiens (human)
protein bindingProtein kinase C alpha typeHomo sapiens (human)
ATP bindingProtein kinase C alpha typeHomo sapiens (human)
zinc ion bindingProtein kinase C alpha typeHomo sapiens (human)
enzyme bindingProtein kinase C alpha typeHomo sapiens (human)
histone H3T6 kinase activityProtein kinase C alpha typeHomo sapiens (human)
protein serine kinase activityProtein kinase C alpha typeHomo sapiens (human)
protein serine/threonine kinase activityProtein kinase C alpha typeHomo sapiens (human)
diacylglycerol bindingProtein kinase C alpha typeHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
ciliary basal bodyProtein kinase C alpha typeHomo sapiens (human)
nucleoplasmProtein kinase C alpha typeHomo sapiens (human)
cytoplasmProtein kinase C alpha typeHomo sapiens (human)
mitochondrionProtein kinase C alpha typeHomo sapiens (human)
endoplasmic reticulumProtein kinase C alpha typeHomo sapiens (human)
cytosolProtein kinase C alpha typeHomo sapiens (human)
plasma membraneProtein kinase C alpha typeHomo sapiens (human)
mitochondrial membraneProtein kinase C alpha typeHomo sapiens (human)
perinuclear region of cytoplasmProtein kinase C alpha typeHomo sapiens (human)
extracellular exosomeProtein kinase C alpha typeHomo sapiens (human)
alphav-beta3 integrin-PKCalpha complexProtein kinase C alpha typeHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID164964Binding affinity (Ki) towards Protein kinase C1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Protein kinase C. Modeling of the binding site and prediction of binding constants.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (38)

TimeframeStudies, This Drug (%)All Drugs %
pre-199019 (50.00)18.7374
1990's8 (21.05)18.2507
2000's2 (5.26)29.6817
2010's5 (13.16)24.3611
2020's4 (10.53)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.22

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.22 (24.57)
Research Supply Index3.66 (2.92)
Research Growth Index4.88 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.22)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (7.89%)6.00%
Case Studies1 (2.63%)4.05%
Observational0 (0.00%)0.25%
Other34 (89.47%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]