Compounds > adenophostin a
Page last updated: 2024-12-07

adenophostin a

Description

adenophostin A: structure given in first source; an inositol-1,4,5-trisphosphate agonist isolated from Penicillium brevicompactum [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID123695
CHEMBL ID204385
CHEBI ID34524
MeSH IDM0225807

Synonyms (18)

Synonym
149091-92-9
adenophostin a
2'-adenylic acid, 3'-o-(3,4-di-o-phosphono-alpha-d-glucopyranosyl)-
2-[5-(6-amino-9h-9-purinyl)-2-hydroxymethyl-4-oxyphosphate-(2r,3r,4r,5r)-tetrahydro-3-furanyloxy]-6-hydroxymethyl-4,5-dioxyphosphate-(2r,3r,4s,5r,6r)-tetrahydro-2h-3-pyranol
bdbm50184325
AC1L3X4M ,
[(2r,3r,4r,5r)-2-(6-aminopurin-9-yl)-4-[(2r,3r,4r,5r,6r)-3-hydroxy-6-(hydroxymethyl)-4,5-diphosphonooxyoxan-2-yl]oxy-5-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate
chebi:34524 ,
CHEMBL204385 ,
2s7ar5svd7 ,
unii-2s7ar5svd7
adenophostin
gtpl4124
{[(2r,3r,4r,5r)-2-(6-amino-9h-purin-9-yl)-4-{[(2r,3r,4r,5r,6r)-3-hydroxy-6-(hydroxymethyl)-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid
[(2r,3r,4r,5r)-2-(6-aminopurin-9-yl)-4-[(2r,3r,4r,5r,6r)-3-hydroxy-6-(hydroxymethyl)-4,5-diphosphonooxy-tetrahydropyran-2-yl]oxy-5-(hydroxymethyl)tetrahydrofuran-3-yl] dihydrogen phosphate
DTXSID10164167
Q4682254
2'-adenylic acid, 3'-o-(3,4-di-o-phosphono-.alpha.-d-glucopyranosyl)-

Research Excerpts

Overview

Adenophostin A (AdA) is a potent agonist of the d-myo-inositol 1,4,5-trisphosphate receptor. AdA is a glyconucleotide natural product with the highest known potency.

ExcerptReferenceRelevance
"Adenophostin A (AdA) is a potent agonist of inositol 1,4,5-trisphosphate receptors (IP(3) R). "( Selective determinants of inositol 1,4,5-trisphosphate and adenophostin A interactions with type 1 inositol 1,4,5-trisphosphate receptors.
Potter, VL; Riley, AM; Rossi, AM; Sureshan, KM; Taylor, CW, 2010)		2.05
"Adenophostin A (AdA) is a potent agonist of the d-myo-inositol 1,4,5-trisphosphate receptor (Ins(1,4,5)P3R). "( 2-Position base-modified analogues of adenophostin A as high-affinity agonists of the D-myo-inositol trisphosphate receptor: in vitro evaluation and molecular modeling.
Potter, BV; Sureshan, KM; Taylor, CW; Tovey, SC; Trusselle, M, 2008)		2.06
"Adenophostin A is a glyconucleotide natural product with the highest known potency for the D-myo-inositol 1,4,5-trisphosphate receptor. "( Inframolecular studies of the protonation of adenophostin A: comparison with 1-D-myo-inositol 1,4,5-trisphosphate.
Felemez, M; Marwood, RD; Potter, BV; Spiess, B, 1999)		2.01
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
disaccharide phosphate
[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)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Inositol 1,4,5-trisphosphate receptor type 1 Rattus norvegicus (Norway rat)EC50 (µMol)0.04580.00150.41308.6340AID1560696; AID1606915; AID261530; AID270919; AID495142; AID661327
Inositol 1,4,5-trisphosphate receptor type 1 Rattus norvegicus (Norway rat)Kd0.00550.00020.02070.1288AID1560698; AID495143
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneInositol 1,4,5-trisphosphate receptor type 1 Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (29)

Assay IDTitleYearJournalArticle
AID231372Ratio to Ins(1,4,5)P3, for the effect on [Ca2+] release from the intracellular stores of permealized hepatocytes (ratio greater than 1 denotes greater potency and less than -1 denotes lesser potency)2001Journal of medicinal chemistry, Jun-21, Volume: 44, Issue:13
Bicyclic analogues of D-myo-inositol 1,4,5-trisphosphate related to adenophostin A: synthesis and biological activity.
AID1560696Agonist activity at rat IP3R1 expressed in human HEK cells assessed as increase in calcium release by Mag-fluo4 dye based assay
AID261530Agonistic potency at rat IP3 type 1 receptor expressed in chicken DT40 cells2006Journal of medicinal chemistry, Mar-23, Volume: 49, Issue:6
A systematic study of C-glucoside trisphosphates as myo-inositol trisphosphate receptor ligands. Synthesis of beta-C-glucoside trisphosphates based on the conformational restriction strategy.
AID270920Activity at rat IP3 type 1 receptor expressed in DT40 cell assessed as calcium ion mobilization relative to IP32006Journal of medicinal chemistry, Sep-21, Volume: 49, Issue:19
Synthesis of adenophostin A analogues conjugating an aromatic group at the 5'-position as potent IP3 receptor ligands.
AID495157Agonist activity to rat recombinant IP3R1 expressed in chicken DT40 cells assessed as calcium release from intracellular stores at maximum effective concentration2009Nature chemical biology, Sep, Volume: 5, Issue:9
Synthetic partial agonists reveal key steps in IP3 receptor activation.
AID195059Fraction of total [Ca2+] stores released by a maximal concentration of the compound2001Journal of medicinal chemistry, Jun-21, Volume: 44, Issue:13
Bicyclic analogues of D-myo-inositol 1,4,5-trisphosphate related to adenophostin A: synthesis and biological activity.
AID1606922Ratio of EC50 for agonist activity at rat IP3R1 expressed in HEK cells assessed as increase in calcium release in cytosol by measuring fluorescence signal by Mag-Fluo4 dye based assay to Kd for binding affinity to IP3R1 in Wistar rat cerebellar membrane2020Journal of medicinal chemistry, 05-28, Volume: 63, Issue:10
Both d- and l-Glucose Polyphosphates Mimic d-
AID226479Hill coefficient for the effect on [Ca2+] release from the intracellular stores of permealized hepatocytes2001Journal of medicinal chemistry, Jun-21, Volume: 44, Issue:13
Bicyclic analogues of D-myo-inositol 1,4,5-trisphosphate related to adenophostin A: synthesis and biological activity.
AID1560699Ratio of EC50 of rat IP3R1 expressed in human HEK cells to Kd of rat IP3R1 expressed in human HEK cells
AID261531Activity at rat IP3 type 1 receptor expressed in chicken DT40 cell by calcium release2006Journal of medicinal chemistry, Mar-23, Volume: 49, Issue:6
A systematic study of C-glucoside trisphosphates as myo-inositol trisphosphate receptor ligands. Synthesis of beta-C-glucoside trisphosphates based on the conformational restriction strategy.
AID270919Activity at rat IP3 type 1 receptor expressed in DT40 cell assessed as calcium ion mobilization2006Journal of medicinal chemistry, Sep-21, Volume: 49, Issue:19
Synthesis of adenophostin A analogues conjugating an aromatic group at the 5'-position as potent IP3 receptor ligands.
AID1560698Displacement of [3H]IP3 from rat IP3R1 expressed in human HEK cells assessed as dissociation constant by radioligand binding assay
AID1606919Agonist activity at rat IP3R1 expressed in HEK cells assessed as increase in calcium release in cytosol by measuring fluorescence signal by Mag-Fluo4 dye based assay relative to control2020Journal of medicinal chemistry, 05-28, Volume: 63, Issue:10
Both d- and l-Glucose Polyphosphates Mimic d-
AID1560700Agonist activity at IP3R1 in rat RBL-2H3 cells assessed as increase in ICRAC at 200 nM at -80 mV holding potential by whole cell patch clamp
AID270921Activity at rat IP3 type 1 receptor expressed in DT40 cell assessed by calcium ion mobilization relative to adenophostin A2006Journal of medicinal chemistry, Sep-21, Volume: 49, Issue:19
Synthesis of adenophostin A analogues conjugating an aromatic group at the 5'-position as potent IP3 receptor ligands.
AID495143Displacement of [3H]IP3 from full-length rat recombinant IP3R1 expressed in chicken DT40 cells by equilibrium competitive binding assay2009Nature chemical biology, Sep, Volume: 5, Issue:9
Synthetic partial agonists reveal key steps in IP3 receptor activation.
AID661327Agonist activity at rat IP3R1 expressed in chicken DT40 cells assessed as induction of Ca2+ release2012Journal of medicinal chemistry, Feb-23, Volume: 55, Issue:4
Contribution of phosphates and adenine to the potency of adenophostins at the IP₃ receptor: synthesis of all possible bisphosphates of adenophostin A.
AID92903Binding affinity towards rat liver membrane, measured using equilibrium competition binding with [3H]Inositol(1,4,5)P32001Journal of medicinal chemistry, Jun-21, Volume: 44, Issue:13
Bicyclic analogues of D-myo-inositol 1,4,5-trisphosphate related to adenophostin A: synthesis and biological activity.
AID1606915Agonist activity at rat IP3R1 expressed in HEK cells assessed as increase in calcium release in cytosol by measuring fluorescence signal by Mag-Fluo4 dye based assay2020Journal of medicinal chemistry, 05-28, Volume: 63, Issue:10
Both d- and l-Glucose Polyphosphates Mimic d-
AID195054Concentration causing maximal effect on [Ca2+] release from the intracellular stores of permealized hepatocytes2001Journal of medicinal chemistry, Jun-21, Volume: 44, Issue:13
Bicyclic analogues of D-myo-inositol 1,4,5-trisphosphate related to adenophostin A: synthesis and biological activity.
AID226480Hill coefficient, measured using equilibrium competition binding with [3H]Inositol(1,4,5)P32001Journal of medicinal chemistry, Jun-21, Volume: 44, Issue:13
Bicyclic analogues of D-myo-inositol 1,4,5-trisphosphate related to adenophostin A: synthesis and biological activity.
AID231371Ratio to Ins(1,4,5)P3 was measured(ratio greater than 1 denotes greater affinity and less than -1 denotes lesser affinity)2001Journal of medicinal chemistry, Jun-21, Volume: 44, Issue:13
Bicyclic analogues of D-myo-inositol 1,4,5-trisphosphate related to adenophostin A: synthesis and biological activity.
AID495142Agonist activity at rat recombinant IP3R1 expressed in chicken DT40 cells assessed as calcium release from intracellular stores2009Nature chemical biology, Sep, Volume: 5, Issue:9
Synthetic partial agonists reveal key steps in IP3 receptor activation.
AID661328Agonist activity at rat IP3R1 expressed in chicken DT40 cells assessed as Ca2+ release relative to control2012Journal of medicinal chemistry, Feb-23, Volume: 55, Issue:4
Contribution of phosphates and adenine to the potency of adenophostins at the IP₃ receptor: synthesis of all possible bisphosphates of adenophostin A.
AID495146Displacement of [3H]IP3 from rat recombinant IP3R1 binding core residue (224-604) expressed in chicken DT40 cells by equilibrium competitive binding assay2009Nature chemical biology, Sep, Volume: 5, Issue:9
Synthetic partial agonists reveal key steps in IP3 receptor activation.
AID1606920Displacement of [3H]-IP3 from IP3R1 in Wistar rat cerebellar membrane measured after 5 mins by liquid scintillation counting method2020Journal of medicinal chemistry, 05-28, Volume: 63, Issue:10
Both d- and l-Glucose Polyphosphates Mimic d-
AID495145Displacement of [3H]IP3 from rat recombinant N-terminal IP3R1 (1-604) expressed in chicken DT40 cells by equilibrium competitive binding assay2009Nature chemical biology, Sep, Volume: 5, Issue:9
Synthetic partial agonists reveal key steps in IP3 receptor activation.
AID1560697Agonist activity at rat IP3R1 expressed in human HEK cells assessed as increase in calcium release by Mag-fluo4 dye based assay relative to control
AID495144Ratio of EC50 to Kd for full-length rat recombinant DT40-IP3R1 expressed in chicken DT40 cells2009Nature chemical biology, Sep, Volume: 5, Issue:9
Synthetic partial agonists reveal key steps in IP3 receptor activation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (90)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's24 (26.67)18.2507
2000's49 (54.44)29.6817
2010's15 (16.67)24.3611
2020's2 (2.22)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.11

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 Index19.11 (24.57)
Research Supply Index4.53 (2.92)
Research Growth Index4.35 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.11)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (2.17%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other90 (97.83%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenine
[no description available]		3.26606-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
chlorine
chloride : A halide anion formed when chlorine picks up an electron to form an an anion.		1.9910halide anion;
monoatomic chlorine		cofactor;
Escherichia coli metabolite;
human metabolite
hydroxide ion
[no description available]		2.0810oxygen hydridemouse metabolite
purine
1H-purine : The 1H-tautomer of purine.. 3H-purine : The 3H-tautomer of purine.. 9H-purine : The 9H-tautomer of purine.. 7H-purine : The 7H-tautomer of purine.		210purine
spermine
[no description available]		2.0210polyazaalkane;
tetramine		antioxidant;
fundamental metabolite;
immunosuppressive agent
uracil
2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder		710pyrimidine nucleobase;
pyrimidone		allergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
prodrug;
Saccharomyces cerevisiae metabolite
2-amino-5-phosphonovalerate
2-Amino-5-phosphonovalerate: The D-enantiomer is a potent and specific antagonist of NMDA glutamate receptors (RECEPTORS, N-METHYL-D-ASPARTATE). The L form is inactive at NMDA receptors but may affect the AP4 (2-amino-4-phosphonobutyrate; APB) excitatory amino acid receptors.		2.0210non-proteinogenic alpha-amino acidNMDA receptor antagonist
2-aminoethoxydiphenyl borate
2-aminoethoxydiphenyl borate: is a novel membrane-penetrable modulator and transient receptor potential channel blocker; structure in first source; do not confuse with 2-APB cpd. 2-aminoethoxydiphenylborane : An organoboron compound that is diphenylborane in which the borane hydrogen is replaced by a 2-aminoethoxy group.		210organoboron compound;
primary amino compound		calcium channel blocker;
IP3 receptor antagonist;
potassium channel opener
caffeine
[no description available]		7.4120purine alkaloid;
trimethylxanthine		adenosine A2A receptor antagonist;
adenosine receptor antagonist;
adjuvant;
central nervous system stimulant;
diuretic;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
environmental contaminant;
food additive;
fungal metabolite;
geroprotector;
human blood serum metabolite;
mouse metabolite;
mutagen;
plant metabolite;
psychotropic drug;
ryanodine receptor agonist;
xenobiotic
verapamil
Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.		2.0210aromatic ether;
nitrile;
polyether;
tertiary amino compound
imipramine
Imipramine: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.. imipramine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.		7.0110dibenzoazepineadrenergic uptake inhibitor;
antidepressant;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
octopamine
Octopamine: An alpha-adrenergic sympathomimetic amine, biosynthesized from tyramine in the CNS and platelets and also in invertebrate nervous systems. It is used to treat hypotension and as a cardiotonic. The natural D(-) form is more potent than the L(+) form in producing cardiovascular adrenergic responses. It is also a neurotransmitter in some invertebrates.. octopamine : A member of the class of phenylethanolamines that is phenol which is substituted at the para- position by a 2-amino-1-hydroxyethyl group. A biogenic phenylethanolamine which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates.		2.0710phenylethanolamines;
tyramines		neurotransmitter
carbachol
Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.		2.4320ammonium salt;
carbamate ester		cardiotonic drug;
miotic;
muscarinic agonist;
nicotinic acetylcholine receptor agonist;
non-narcotic analgesic
levodopa
Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease		2.0210amino acid zwitterion;
dopa;
L-tyrosine derivative;
non-proteinogenic L-alpha-amino acid		allelochemical;
antidyskinesia agent;
antiparkinson drug;
dopaminergic agent;
hapten;
human metabolite;
mouse metabolite;
neurotoxin;
plant growth retardant;
plant metabolite;
prodrug
cycloheximide
Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.		210antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor
egtazic acid
Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.		3.2660diether;
tertiary amino compound;
tetracarboxylic acid		chelator
framycetin
Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.		2.0110aminoglycosideallergen;
antibacterial drug;
Escherichia coli metabolite
oxazoles
Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.		2.42201,3-oxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
bicuculline
Bicuculline: An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.. bicuculline : A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.		2.0210benzylisoquinoline alkaloid;
isoquinoline alkaloid;
isoquinolines		agrochemical;
central nervous system stimulant;
GABA-gated chloride channel antagonist;
GABAA receptor antagonist;
neurotoxin
dibutyldichlorotin
[no description available]		1.9910
fluorescein-5-isothiocyanate
Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.		2.0510fluorescein isothiocyanate
manganese
Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.		1.9910elemental manganese;
manganese group element atom		Escherichia coli metabolite;
micronutrient
gold
Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.		2.110copper group element atom;
elemental gold
adenosine diphosphate ribose
Adenosine Diphosphate Ribose: An ester formed between the aldehydic carbon of RIBOSE and the terminal phosphate of ADENOSINE DIPHOSPHATE. It is produced by the hydrolysis of nicotinamide-adenine dinucleotide (NAD) by a variety of enzymes, some of which transfer an ADP-ribosyl group to target proteins.		3.5420ADP-sugarEscherichia coli metabolite;
mouse metabolite
fura-2
Fura-2: A fluorescent calcium chelating agent which is used to study intracellular calcium in tissues.		210
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		11.88860adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		2.940D-glucopyranoseepitope;
mouse metabolite
triazoles
Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.		2.11101,2,3-triazole
panose
panose : A trisaccharide composed of D-glucopyranose units.		2.0110trisaccharideplant metabolite
1,2-bis(2-aminophenoxy)ethane-n,n,n',n'-tetraacetic acid
1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid: structure in first source		2.9340polyamino carboxylic acid;
tetracarboxylic acid		chelator
u 73122
1-(6-((3-methoxyestra-1,3,5(10)-trien-17-yl)amino)hexyl)-1H-pyrrole-2,5-dione: structure given in first source. U-73122 : An aza-steroid that is 3-O-methyl-17beta-estradiol in which the 17beta-hydroxy group is replaced by a 6-(maleimid-1-yl)hexylamino group. An inibitor of phospholipase C.		3.1250aromatic ether;
aza-steroid;
maleimides		EC 3.1.4.11 (phosphoinositide phospholipase C) inhibitor
inositol 2,4,5-trisphosphate
[no description available]		2.9240
cyclic adp-ribose
Cyclic ADP-Ribose: A pyridine nucleotide that mobilizes CALCIUM. It is synthesized from nicotinamide adenine dinucleotide (NAD) by ADP RIBOSE CYCLASE.		7.4120cyclic purine nucleotide;
nucleotide-sugar		metabolite;
ryanodine receptor agonist
naadp
nicotinic acid-adenine dinucleotide phosphate : A nicotinic acid dinucleotide that is NADP(+) in which the carboxamide group on the pyridine ring is replaced by a carboxy group.		3.5920nicotinic acid dinucleotidecalcium channel agonist;
metabolite;
signalling molecule
inositol 4,5-bisphosphate
inositol 4,5-bisphosphate: RN given refers to cpd without isomeric designation		2.0710myo-inositol bisphosphate
glycerophosphoinositol 4,5-bisphosphate
glycerophosphoinositol 4,5-bisphosphate: do not confuse with phosphatidylinositols which have fatty acids esterified at the C-1 and C-2 hydroxyl groups of glycerol		210
deoxycholic acid
Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.. deoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.		2.0110bile acid;
C24-steroid;
dihydroxy-5beta-cholanic acid		human blood serum metabolite
inositol 1,4,5-trisphosphate
Inositol 1,4,5-Trisphosphate: Intracellular messenger formed by the action of phospholipase C on phosphatidylinositol 4,5-bisphosphate, which is one of the phospholipids that make up the cell membrane. Inositol 1,4,5-trisphosphate is released into the cytoplasm where it releases calcium ions from internal stores within the cell's endoplasmic reticulum. These calcium ions stimulate the activity of B kinase or calmodulin.		6.46560myo-inositol trisphosphatemouse metabolite
ryanodine
Ryanodine: A methylpyrrole-carboxylate from RYANIA that disrupts the RYANODINE RECEPTOR CALCIUM RELEASE CHANNEL to modify CALCIUM release from SARCOPLASMIC RETICULUM resulting in alteration of MUSCLE CONTRACTION. It was previously used in INSECTICIDES. It is used experimentally in conjunction with THAPSIGARGIN and other inhibitors of CALCIUM ATPASE uptake of calcium into SARCOPLASMIC RETICULUM.. ryanodine : An insecticide alkaloid isolated from South American plant Ryania speciosa.		2.4220
arachidonic acid
icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.		2.4720icosa-5,8,11,14-tetraenoic acid;
long-chain fatty acid;
omega-6 fatty acid		Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
human metabolite;
mouse metabolite
thapsigargin
Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.		2.9440butyrate ester;
organic heterotricyclic compound;
sesquiterpene lactone		calcium channel blocker;
EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
glycosides
[no description available]		2.9240
adenophostin b
adenophostin B: structure given in first source; an inositol-1,4,5-trisphosphate agonist isolated from Penicillium brevicompactum		3.2460disaccharide phosphate
nadp
[no description available]		3.5920
1,2-bis(2-aminophenoxy)ethane n,n,n',n'-tetraacetic acid acetoxymethyl ester
[no description available]		210
3-deoxy-3-fluoroinositol 1,4,5-trisphosphate
[no description available]		2.0210
6-cyano-7-nitroquinoxaline-2,3-dione
6-Cyano-7-nitroquinoxaline-2,3-dione: A potent excitatory amino acid antagonist with a preference for non-NMDA iontropic receptors. It is used primarily as a research tool.		2.4220quinoxaline derivative
myelin basic protein
Myelin Basic Protein: An abundant cytosolic protein that plays a critical role in the structure of multilamellar myelin. Myelin basic protein binds to the cytosolic sides of myelin cell membranes and causes a tight adhesion between opposing cell membranes.		2.0210
barium
Barium: An element of the alkaline earth group of metals. It has an atomic symbol Ba, atomic number 56, and atomic weight 138. All of its acid-soluble salts are poisonous.		1.9910alkaline earth metal atom;
elemental barium
strontium
Strontium: An element of the alkaline earth family of metals. It has the atomic symbol Sr, atomic number 38, and atomic weight 87.62.		2.6930alkaline earth metal atom
phosphorus
Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.		2.0210monoatomic phosphorus;
nonmetal atom;
pnictogen		macronutrient
bafilomycin a1
bafilomycin A1: from Streptomyces griseus; structure given in first source. bafilomycin A1 : The most used of the bafilomycins, a family of toxic macrolide antibiotics derived from Streptomyces griseus.		2.0710cyclic hemiketal;
macrolide antibiotic;
oxanes		apoptosis inducer;
autophagy inhibitor;
bacterial metabolite;
EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor;
EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor;
ferroptosis inhibitor;
fungicide;
potassium ionophore;
toxin
sq-23377
Ionomycin: A divalent calcium ionophore that is widely used as a tool to investigate the role of intracellular calcium in cellular processes.. ionomycin : A very long-chain fatty acid that is docosa-10,16-dienoic acid which is substituted by methyl groups at positions 4, 6, 8, 12, 14, 18 and 20, by hydroxy groups at positions 11, 19 and 21, and by a (2',5-dimethyloctahydro-2,2'-bifuran-5-yl)ethanol group at position 21. An ionophore produced by Streptomyces conglobatus, it is used in research to raise the intracellular level of Ca(2+) and as a research tool to understand Ca(2+) transport across biological membranes.		210cyclic ether;
enol;
polyunsaturated fatty acid;
very long-chain fatty acid		calcium ionophore;
metabolite
cyclophostin
cyclophostin: from Streptomyces lavendulae; structure given in first source		710
xestospongin a
xestospongin A: blocks inositol 1,4,5-trisphosphate receptors; structure in first source; from Xestospongia sponge		2.4220
ribose
ribopyranose : The pyranose form of ribose.		210D-ribose;
ribopyranose
calcimycin
Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.		210benzoxazole
thimerosal
Thimerosal: An ethylmercury-sulfidobenzoate that has been used as a preservative in VACCINES; ANTIVENINS; and OINTMENTS. It was formerly used as a topical antiseptic. It degrades to ethylmercury and thiosalicylate.. thimerosal : An alkylmercury compound (approximately 49% mercury by weight) used as an antiseptic and antifungal agent.		2.420alkylmercury compoundantifungal drug;
antiseptic drug;
disinfectant;
drug allergen
picrotoxin
Picrotoxin: A noncompetitive antagonist at GABA-A receptors and thus a convulsant. Picrotoxin blocks the GAMMA-AMINOBUTYRIC ACID-activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially the barbiturates.. picrotoxin : A mixture consisting of equimolar amounts of picrotoxinin and picrotin found in the climbing plant Anamirta cocculus.		2.0210
cyclosporine
Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).		2.0110
guanosine 5'-o-(3-thiotriphosphate)
Guanosine 5'-O-(3-Thiotriphosphate): Guanosine 5'-(trihydrogen diphosphate), monoanhydride with phosphorothioic acid. A stable GTP analog which enjoys a variety of physiological actions such as stimulation of guanine nucleotide-binding proteins, phosphoinositide hydrolysis, cyclic AMP accumulation, and activation of specific proto-oncogenes.		210nucleoside triphosphate analogue
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Ovary
[description not available]		02.110
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		02.110
Arrhythmia
[description not available]		03.0310
Arrhythmias, Cardiac
Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.		03.0310
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)		01.9810
Basophilic Leukemia, Acute
[description not available]		01.9910
Leukemia, Basophilic, Acute
A rare acute myeloid leukemia in which the primary differentiation is to BASOPHILS. It is characterized by an extreme increase of immature basophilic granulated cells in the bone marrow and blood. Mature basophils are usually sparse.		01.9910
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