gambierol profile

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

ID Source	ID
PubMed CID	6442244
CHEMBL ID	266438
MeSH ID	M0400087

Synonym
CHEMBL266438
(-)-gambierol
unii-844q8wc5f6
844q8wc5f6 ,
gambierol
146763-62-4
(1s,3r,5s,7r,10s,11r,13s,15r,17s,20r,22s,24r,26s,27s,29s,31r,33s,35r)-11-[(1z,3z)-hepta-1,3,6-trienyl]-29-(3-hydroxypropyl)-3,5,10,24,26-pentamethyl-2,6,12,16,21,25,30,34-octaoxaoctacyclo[18.16.0.03,17.05,15.07,13.022,35.024,33.026,31]hexatriacont-8-ene-1
DTXSID30880110

Excerpt	Reference	Relevance
"Gambierol is a polycyclic ether toxin, isolated as a toxic constituent from the marine dinoflagellate Gambierdiscus toxicus. "	( Synthesis and biological evaluation of gambierol analogues. Fuwa, H; Kainuma, N; Sasaki, M; Satake, M, 2003)	2.03
"Gambierol is a marine polycyclic ether toxin produced by the marine dinoflagellate Gambierdiscus toxicus and is a member of the ciguatoxin toxin family. "	( Gambierol inhibition of voltage-gated potassium channels augments spontaneous Ca2+ oscillations in cerebrocortical neurons. Busse, E; Cao, Z; Cui, Y; Mehrotra, S; Murray, TF; Rainier, JD, 2014)	3.29
"Gambierol is a marine polycyclic ether toxin, produced along with ciguatoxin congeners by the dinoflagellate Gambierdiscus toxicus. "	( Potassium currents inhibition by gambierol analogs prevents human T lymphocyte activation. Botana, LM; Fuwa, H; Martín, V; Rubiolo, JA; Sasaki, M; Vale, C, 2015)	2.14
"Gambierol is a marine polycyclic ether toxin belonging to the group of ciguatera toxins. "	( A polyether biotoxin binding site on the lipid-exposed face of the pore domain of Kv channels revealed by the marine toxin gambierol. Cuypers, E; Johnson, HW; Kopljar, I; Labro, AJ; Rainier, JD; Snyders, DJ; Tytgat, J, 2009)	2
"Gambierol is a marine polyether ladder toxin derived from the dinoflagellate Gambierdiscus toxicus. "	( Calcium oscillations induced by gambierol in cerebellar granule cells. Alonso, E; Botana, LM; Fuwa, H; Konno, Y; Perez, S; Sasaki, M; Vale, C; Vieytes, MR, 2010)	2.09
"Gambierol is a complex marine toxin first isolated with ciguatoxins from cell cultures of the toxic dinoflagellate Gambierdiscus toxicus. "	( The marine polyether gambierol enhances muscle contraction and blocks a transient K(+) current in skeletal muscle cells. Benoit, E; Botana, LM; Fuwa, H; Girard, E; Louzao, MC; Molgó, J; Ouanounou, G; Sasaki, M; Schlumberger, S, 2010)	2.12
"Gambierol is a potent neurotoxin that belongs to the family of marine polycyclic ether natural products and primarily targets voltage-gated potassium channels (K(v) channels) in excitable membranes. "	( Design and synthesis of skeletal analogues of gambierol: attenuation of amyloid-β and tau pathology with voltage-gated potassium channel and N-methyl-D-aspartate receptor implications. Alonso, E; Botana, LM; Fuwa, H; Giménez-Llort, L; Goto, T; Konno, Y; LaFerla, FM; Sasaki, M; Suga, Y; Vale, C; Vieytes, MR, 2012)	2.08
"Gambierol is a marine polycyclic ether toxin, first isolated along with ciguatoxin congeners from the dinoflagellate Gambierdiscus toxicus."	( Effect of gambierol and its tetracyclic and heptacyclic analogues in cultured cerebellar neurons: a structure-activity relationships study. Alonso, E; Botana, LM; Fuwa, H; Goto, T; Konno, Y; Pérez, S; Sasaki, M; Suga, Y; Vale, C; Vieytes, MR, 2012)	1.5
"Gambierol is a polycyclic ether toxin, which has been isolated from the marine dinoflagellate Gambierdiscus toxicus. "	( Diverted total synthesis and biological evaluation of gambierol analogues: elucidation of crucial structural elements for potent toxicity. Fuwa, H; Kainuma, N; Sasaki, M; Satake, M; Tachibana, K; Tsukano, C, 2004)	2.01
"Gambierol is a polycyclic ether toxin with the same biogenetic origin as ciguatoxins. "	( The sodium channel of human excitable cells is a target for gambierol. Botana, LM; Cagide, E; Fuwa, H; Louzao, MC; Sasaki, M; Vieytes, MR; Yasumoto, T, 2006)	2.02

Excerpt	Reference	Relevance
"Gambierol has been demonstrated to be either a low-efficacy partial agonist/antagonist of voltage-gated sodium channels or a potent blocker of voltage-gated potassium channels (Kvs)."	( Gambierol inhibition of voltage-gated potassium channels augments spontaneous Ca2+ oscillations in cerebrocortical neurons. Busse, E; Cao, Z; Cui, Y; Mehrotra, S; Murray, TF; Rainier, JD, 2014)	2.57
"Gambierol has been associated with neurological symptoms in humans even though its mechanism of action has not been fully characterized."	( The sodium channel of human excitable cells is a target for gambierol. Botana, LM; Cagide, E; Fuwa, H; Louzao, MC; Sasaki, M; Vieytes, MR; Yasumoto, T, 2006)	1.3

Excerpt	Reference	Relevance
" In many cases, the lack of toxic material turns out to be an obstacle to make the toxicological investigations needed."	( Comparative cytotoxicity of gambierol versus other marine neurotoxins. Ares, IR; Botana, LM; Cagide, E; Espiña, B; Fuwa, H; Konno, Y; Louzao, MC; Paquette, LA; Sasaki, M; Tsukano, C; Vieytes, MR; Yasumoto, T; Yotsu-Yamashita, M, 2011)	0.66

Assay ID	Title	Year	Journal	Article
AID212037	Minimal lethal dose of compound expressed as toxicity against male mice (ddY strain) after intraperitoneal administration	2003	Bioorganic & medicinal chemistry letters, Aug-04, Volume: 13, Issue:15	Synthesis and biological evaluation of gambierol analogues.
AID1177025	Induction of leak current in wild-type CHO cells by electrophysiology method	2015	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 25, Issue:3	Evaluation of gambierol and its analogs for their inhibition of human Kv1.2 and cytotoxicity.
AID1177027	Cytotoxicity against CHO cells transfected with human Kv 1.2 assessed as growth inhibition after 72 hrs by WST-8 assay	2015	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 25, Issue:3	Evaluation of gambierol and its analogs for their inhibition of human Kv1.2 and cytotoxicity.
AID1177024	Inhibition of human Kv 1.2 stably expressed in CHO cells by whole cell patch clamp method	2015	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 25, Issue:3	Evaluation of gambierol and its analogs for their inhibition of human Kv1.2 and cytotoxicity.
AID1177026	Cytotoxicity against wild-type CHO cells assessed as growth inhibition after 72 hrs by WST-8 assay	2015	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 25, Issue:3	Evaluation of gambierol and its analogs for their inhibition of human Kv1.2 and cytotoxicity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	29 (65.91)	29.6817
2010's	14 (31.82)	24.3611
2020's	1 (2.27)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	4 (9.09%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	40 (90.91%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	2.13	1	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
tubocurarine Tubocurarine: A neuromuscular blocker and active ingredient in CURARE; plant based alkaloid of Menispermaceae.. tubocurarine : A benzylisoquinoline alkaloid muscle relaxant which constitutes the active component of curare.. isoquinoline alkaloid : Any alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.	2.05	1	bisbenzylisoquinoline alkaloid	drug allergen; muscle relaxant; nicotinic antagonist
ethylene oxide Ethylene Oxide: A colorless and flammable gas at room temperature and pressure. Ethylene oxide is a bactericidal, fungicidal, and sporicidal disinfectant. It is effective against most micro-organisms, including viruses. It is used as a fumigant for foodstuffs and textiles and as an agent for the gaseous sterilization of heat-labile pharmaceutical and surgical materials. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p794). oxirane : A saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.	2.05	1	gas molecular entity; oxacycle; saturated organic heteromonocyclic parent	allergen; mouse metabolite; mutagen
vinyl bromide vinyl bromide: structure	2.01	1	bromoalkene; monohaloethene
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.01	1	metal allergen; nickel group element atom; platinum group metal atom
samarium Samarium: An element of the rare earth family of metals. It has the atomic symbol Sm, atomic number 62, and atomic weight 150.36. The oxide is used in the control rods of some nuclear reactors.	3.15	1	f-block element atom; lanthanoid atom
iodine [no description available]	3.15	1	halide anion; monoatomic iodine	human metabolite
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.05	1	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
sperm motility inhibitor 2 [no description available]	3.15	1
glycosides [no description available]	7.93	4
thiopental Thiopental: A barbiturate that is administered intravenously for the induction of general anesthesia or for the production of complete anesthesia of short duration.. thiopental : A barbiturate, the structure of which is that of 2-thiobarbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	3.14	1	barbiturates	anticonvulsant; drug allergen; environmental contaminant; intravenous anaesthetic; sedative; xenobiotic
thiobutabarbital thiobutabarbital: RN given refers to parent cpd	3.14	1
mucocin mucocin: an acetogenin from Annonaceae; structure in first source	3.15	1	polyketide
ciguatoxins Ciguatoxins: Polycyclic ethers produced by Gambierdiscus (DINOFLAGELLATES) from gambiertoxins, which are ingested by fish which in turn may be ingested by humans who are susceptible to the CIGUATERA POISONING.. ciguatoxin CTX1B : A ciguatoxin comprising a sequence of twelve trans-fused six-, seven-, eight- and nine-membered rings and a spiro-fused five-membered ring. A commonly encountered fish toxin.. ciguatoxin : Ciguatoxins are cyclic polyether toxins, derived from marine dinoflagellates, which are responsible for the symptoms of ciguatera poisoning. Ingestion of tropical and subtropical fin fish contaminated by ciguatoxins results in an illness characterised by neurological, cardiovascular and gastrointestinal disorders.	7.35	44	ciguatoxin	metabolite
gambieric acid a gambieric acid A: structure given in first source; a polyether isolated from the marine dinoflagellate Gambierdiscus toxicus	2.42	2
gambieric acid b gambieric acid B: structure given in first source; a polyether isolated from the marine dinoflagellate Gambierdiscus toxicus	2.03	1
concanamycin a concanamycin A: from Streptomyces diastatochromogenes S-45; inhibits vacuolar H+ ATPase. concanamycin A : A concanamycin in which the lactone ring contains 4 double bonds and is substituted by 4 methyl groups, 2 hydroxy groups, 2 methoxy groups and an ethyl group.	2.11	1	carbamate ester; concanamycin	antifungal agent; EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor; metabolite
ciguatoxin 3c ciguatoxin 3C: structure in first source	2.03	1
hemibrevetoxin b hemibrevetoxin B: RN given for (2R-(2alpha.4alpha.4abeta.5abeta.7abeta.9alpha(Z),10beta,12alpha,13aalpha,14aalpha))-isomer; structure in first source	3.15	1	oxacycle
brevetoxin b brevetoxin B: from dinoflagellate Gymnodinium breve	4.06	2	ciguatoxin
gymnocin a gymnocin A: structure in first source	3.54	2
veratridine Veratridine: A benzoate-cevane found in VERATRUM and Schoenocaulon. It activates SODIUM CHANNELS to stay open longer than normal.	2.03	1
yessotoxin yessotoxin: produced by dinoflagellates and accumulated in invertebrates (e.g., Patinopecten gessoensis also known as YESSO SCALLOP) that feed on them. RN given refers to parent compound	2.42	2	ciguatoxin
adriatoxin adriatoxin: structure in first source	2.03	1
brevetoxin brevetoxin: from Ptychodiscus brevis	8.84	3
saxitoxin Saxitoxin: A compound that contains a reduced purine ring system but is not biosynthetically related to the purine alkaloids. It is a poison found in certain edible mollusks at certain times; elaborated by GONYAULAX and consumed by mollusks, fishes, etc. without ill effects. It is neurotoxic and causes RESPIRATORY PARALYSIS and other effects in MAMMALS, known as paralytic SHELLFISH poisoning.. saxitoxin : An alkaloid isolated from the marine dinoflagellates and cyanobacteria that causes paralytic shellfish poisoning.	2.03	1	alkaloid; carbamate ester; guanidines; ketone hydrate; paralytic shellfish toxin; pyrrolopurine	cyanotoxin; marine metabolite; neurotoxin; sodium channel blocker; toxin
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	2.05	1	ketal
maitotoxin [no description available]	9.91	4
ciguatoxin 2 ciguatoxin 2: ciguatoxin -2 is a diastereomer of ciguatoxin-3; differs only in stereochemistry at carbon 52; structure given in first source	2.03	1

Condition	Relationship Strength	Studies
Ciguatera [description not available]	9.06	5
Ciguatera Poisoning Poisoning caused by ingestion of SEAFOOD containing microgram levels of CIGUATOXINS. The poisoning is characterized by gastrointestinal, neurological and cardiovascular disturbances.	4.06	5
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	7.05	1
Acute Confusional Senile Dementia [description not available]	2.07	1
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	2.07	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.01	1
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	2.03	1

gambierol

Description

Cross-References

Synonyms (8)

Research Excerpts

Overview

Effects

Toxicity

Bioassays (5)

Research

Studies (44)

Market Indicators

Research Demand Index: 19.84

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gambierol

Description

Cross-References

Synonyms (8)

Research Excerpts

Overview

Effects

Toxicity

Bioassays (5)

Research

Studies (44)

Market Indicators

Research Demand Index: 19.84

Study Types

Related Drugs (29)

Related Conditions (7)