Page last updated: 2024-11-11

sq-23377

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Description

Ionomycin: A divalent calcium ionophore that is widely used as a tool to investigate the role of intracellular calcium in cellular processes. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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. [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 CID6912226
CHEMBL ID501617
CHEBI ID63954
SCHEMBL ID17265597
MeSH IDM0351548

Synonyms (32)

Synonym
HSCI1_000207
ionomycin
ionomycin from streptomyces conglobatus, >=98% (hplc)
ionomycin, free acid, streptomyces conglobatus
(4r,6s,8s,10z,12r,14r,16e,18r,19r,20s,21s)-11,19,21-trihydroxy-22-{(2s,2'r,5s,5's)-5'-[(1r)-1-hydroxyethyl]-2,5'-dimethyloctahydro-2,2'-bifuran-5-yl}-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
sq23377
sq 23377
56092-81-0
sq-23377
CHEMBL501617
chebi:63954 ,
(4r,6s,8s,10z,12r,14r,16e,18r,19r,20s,21s)-11,19,21-trihydroxy-22-[(2s,5s)-5-[(2r,5s)-5-[(1r)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
unii-54v905v6at
54v905v6at ,
c41h72o9
ionomycin free acid
(4r,6s,8s,10z,12r,14r,16e,18r,19r,20s,21s)-11,19,21-trihydroxy-4,6,8,12,14,18,20-heptamethyl-22-[(2s,2'r,5s,5's)-octahydro-5'-[(1r)-1-hydroxyethyl]-2,5'-dimethyl[2,2'-bifuran]-5-yl]-9-oxo-10,16-docosadienoic acid
HB1002
AKOS024456942
HMS3403I13
SCHEMBL17265597
DTXSID2040521
HY-13434
CS-0006887
(4r,6s,8s,10z,12r,14r,16e,18r,19r,20s,21s)-11,19,21-trihydroxy-22-((2s,2'r,5s,5's)-5'-((r)-1-hydroxyethyl)-2,5'-dimethyloctahydro-[2,2'-bifuran]-5-yl)-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
PGHMRUGBZOYCAA-ADZNBVRBSA-N
10,16-docosadienoic acid, 11,19,21-trihydroxy-4,6,8,12,14,18,20-heptamethyl-22-((2s,2'r,5s,5's)-octahydro-5'-((1r)-1-hydroxyethyl)-2,5'-dimethyl(2,2'-bifuran)-5-yl)-9-oxo-, (4r,6s,8s,10z,12r,14r,16e,18r,19r,20s,21s)-
AS-56129
AKOS037645010
(4r,6s,8s,10z,12r,14r,16e,18r,19r,20s,21s)-11,19,21-trihydroxy-22-((2s,2'r,5s,5's)-5'-((r)-1-hydroxyethyl)-2,5'-dimethyloctahydro-[2,2'-bifuran]-5-yl)-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoicacid
10,16-docosadienoic acid, 11,19,21-trihydroxy-4,6,8,12,14,18,20-heptamethyl-22-[(2s,2'r,5s,5's)-octahydro-5'-[(1r)-1-hydroxyethyl]-2,5'-dimethyl[2,2'-bifuran]-5-yl]-9-oxo-, (4r,6s,8s,10z,12r,14r,16e,1 8r,19r,20s,21s)-
EX-A8018F

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" A broad spectrum of model toxic compounds was evaluated for toxicity on mouse skin JB6 cells in culture."( Studies of skin toxicity in vitro: dose-response studies on JB6 cells.
Berezesky, IK; Fitzpatrick, MJ; Jain, PT; Phelps, PC; Trump, BF, 1992
)
0.28
" It is concluded that a) plasma membrane indicator dyes, not neutral red, might be better indicators of cytotoxicity occurring during cryopreservation; b) DMSO might be toxic to lysosomes during cryopreservation of cultured cells; and c) although [Ca+2]e can contribute to cytotoxicity, the presence of [Ca+2]e might not influence cryopreservation-induced cytotoxicity."( Extracellular calcium does not contribute to cryopreservation-induced cytotoxicity.
Baust, J; Danks, AM; Im, J; Isaacson, RL; Rhoads, LS; Van Buskirk, RG; Warner, A, 1993
)
0.29
" The clinical usefulness of tacrolimus is limited, however, by severe adverse effects, including neurotoxicity and nephrotoxicity."( A tacrolimus-related immunosuppressant with reduced toxicity.
Barker, J; DaSilva, C; Dumont, FJ; Koo, G; Koprak, S; Parsons, WH; Pivnichny, J; Sigal, NH; Sinclair, PJ; Singer, I; Staruch, MJ; Talento, A; Williamson, AR; Wong, F; Woods, J; Wyvratt, M, 1998
)
0.3

Pharmacokinetics

ExcerptReferenceRelevance
" Time kinetic analysis of NFAT1 inhibition in plasma from stable renal transplant recipients before and after an in vivo dose with tacrolimus correlated with the expected pharmacokinetic profile of tacrolimus."( Nuclear translocation of nuclear factor of activated T cells (NFAT) as a quantitative pharmacodynamic parameter for tacrolimus.
Maguire, O; Minderman, H; O'Loughlin, KL; Tornatore, KM; Venuto, RC, 2013
)
0.39

Compound-Compound Interactions

ExcerptReferenceRelevance
"In the present work, nerve growth factor (NGF) was used in combination with the calcium ionophore, ionomycin or dibutyryl cyclic AMP (dbcAMP), to study the connection between neuronal differentiation and extracellular signal-regulated kinase (ERK) activation of PC12 rat pheochromocytoma cells expressing a dominant negative, Ha-Ras Asn17 protein."( Nerve growth factor in combination with second messenger analogues causes neuronal differentiation of PC12 cells expressing a dominant inhibitory Ras protein without inducing activation of extracellular signal-regulated kinases.
Boglári, G; Szeberényi, J, 2001
)
0.31
" To increase the efficiency of interspecies somatic cell nuclear transfer, in the present study we introduced a method of whole cell intracytoplasmic injection (WCICI) combined with chemical enucleation into panda-rabbit nuclear transfer and assessed the effects of this method on the enucleation rate of rabbit oocytes and the in vitro development and spindle structures of giant panda-rabbit reconstructed embryos."( The effects of chemical enucleation combined with whole cell intracytoplasmic injection on panda-rabbit interspecies nuclear transfer.
Chen, DY; Jiang, MX; Liu, SZ; Sun, QY; Yang, CX; Zhang, LS; Zheng, YL, 2004
)
0.32

Bioavailability

ExcerptReferenceRelevance
" Impairment of glucose bioavailability reduced Rh 123 fluorescence."( Mitochondrial membrane potential measurement in rat cerebellar neurons by flow cytometry.
Camarasa, J; Camins, A; Comas, J; Escubedo, E; Gabriel, C; Sureda, FX, 1997
)
0.3
" These data establish a general strategy for enhancing delivery of poorly absorbed drugs across tissue barriers and provide a new topical approach to the treatment of inflammatory skin disorders."( Conjugation of arginine oligomers to cyclosporin A facilitates topical delivery and inhibition of inflammation.
Garlington, S; Khavari, PA; Kirschberg, T; Kreider, E; Lin, Q; McGrane, PL; Rothbard, JB; Wender, PA, 2000
)
0.31
"N-acetyl-L-cysteine exerts direct anti-aggregating effects through an increased bioavailability of platelet nitric oxide."( N-acetyl-L-cysteine exerts direct anti-aggregating effect on human platelets.
Anfossi, G; Cavalot, F; Massucco, P; Mattiello, L; Russo, I; Trovati, M, 2001
)
0.31
" This may have practical applications in drug delivery and bioavailability of hydrophobic peptides."( Lipidation and glycosylation of a T cell antigen receptor (TCR) transmembrane hydrophobic peptide dramatically enhances in vitro and in vivo function.
Ali, M; Amon, MA; Bender, V; Chan, YN; Manolios, N; Toth, I, 2006
)
0.33
" Furthermore, these stores, albeit small, may provide an additional mechanism for the regulation of vascular tone, especially under conditions, such as diabetes, in which nitric oxide generation or bioavailability is compromised; however, additional studies are required to determine not only whether there are additional chemical storage forms of nitric oxide, but also the location of such stores."( Nitrosothiol stores in vascular tissue: modulation by ultraviolet light, acetylcholine and ionomycin.
Cheng, ZJ; Ding, H; Ellis, A; Hollenberg, MD; Jiang, Y; Li, Y; Ng, ES; Triggle, CR, 2007
)
0.34
" IH causes oxidative stress that may limit bioavailability of the endothelium-derived vasodilator nitric oxide (NO) and thus contribute to this hypertensive response."( Intermittent hypoxia augments pulmonary vascular smooth muscle reactivity to NO: regulation by reactive oxygen species.
Jernigan, NL; Kanagy, NL; Norton, CE; Resta, TC; Walker, BR, 2011
)
0.37

Dosage Studied

ExcerptRelevanceReference
" Ninety percent of K+/86Rb accumulation was blocked by ouabain, and the dose-response curve of inhibition by ouabain was monophasic (IC50, approximately 80 microM), suggesting the role of a single type of Na+/K+ pump (alpha-isoenzyme) in 86Rb accumulation by rat glomerulosa cells."( Angiotensin-II inhibits Na+/K+ pump in rat adrenal glomerulosa cells: possible contribution to stimulation of aldosterone production.
Balla, T; Csordás, G; Enyedi, P; Hajnóczky, G; Hunyady, L; Kalapos, MP; Spät, A, 1992
)
0.28
" Millimolar concentration of ATP, which is present physiologically, will shift the dose-response relation of IP3 toward the higher IP3 concentration and enhance the maximal effect of IP3."( Effects of adenine nucleotides on inositol 1,4,5-trisphosphate-induced calcium release in vascular smooth muscle cells.
Iino, M, 1991
)
0.28
" The lipopeptides N-palmitoyl-(S)-[2,3-bis(palmitoyloxy)-(2RS)- propyl]-(R)-cysteinylalanylglycine, N-palmitoyl-(S)-[2,3-bis(palmitoyloxy)- (2RS)-propyl]-(R)-cysteinylseryl-lysyl-lysyl-lysine and (S)-(1,2- dicarboxyhexadecyl)ethyl-N-palmitoylcysteinylseryl-lysyl-lys yl-lysine stimulated both parameters, but the maximal effects on nitrite formation and the shape of the dose-response curves did not parallel the effects on [Ca2+]i."( Induction and activity of NO synthase in bone-marrow-derived macrophages are independent of Ca2+.
Bessler, W; Busse, R; Hauschildt, S; Kohler, J; Lückhoff, A; Mülsch, A, 1990
)
0.28
" However, in the presence of ionomycin the dose-response of 8-bromo-cAMP (Br-cAMP) with respect to uPA mRNA accumulation was shifted toward the lower concentrations of Br-cAMP."( Ca2+ potentiates cAMP-dependent expression of urokinase-type plasminogen activator gene through a calmodulin- and protein kinase C-independent mechanism.
Hagmann, J; Kiefer, B; Nagamine, Y; Ziegler, A, 1990
)
0.28
" First, in dose-response experiments, it was shown that 10 times the concentration of IL-4 was required for CD23 than for sIgM expression."( Independent regulation of interleukin 4 (IL-4)-induced expression of human B cell surface CD23 and IgM: functional evidence for two IL-4 receptors.
Callard, RE; Rigley, KP; Thurstan, SM, 1991
)
0.28
" Dose-response curves for the inhibitory effects of the anti-oxidants on DNA synthesis and ODC activity at 48 h after mitogen addition were very similar."( Effects of anti-oxidants on ornithine decarboxylase in mitogenically-activated T lymphocytes.
Fragonas, JC; Hunt, NH, 1992
)
0.28
" Dose-response analysis of peak and plateau phases of intracellular Ca2+ shows different agonist potencies for both phases, carbachol being more potent for the plateau phase."( Muscarinic-receptor-mediated changes in intracellular Ca2+ and inositol 1,4,5-trisphosphate mass in a human neuroblastoma cell line, SH-SY5Y.
Lambert, DG; Nahorski, SR, 1990
)
0.28
" In dose-response curves, the isoproterenol-sensitive K+ efflux was half-maximally inhibited (IC50) with 2-5 X 10(-10) M of isoproterenol concentration."( Stimulation of beta-adrenoceptors inhibits calcium-dependent potassium-channels in mouse macrophages.
Braquet, P; Dausse, JP; Garay, R; Hannaert, P; Rosati, C, 1986
)
0.27
" The time course and dose-response for the effect of PMA at 23 degrees C closely correlate with the phosphorylation of a set of relatively "slowly" phosphorylated proteins (P20, P35, P41, P60), but not the rapidly phosphorylated P47 protein."( Synergistic release of arachidonic acid from platelets by activators of protein kinase C and Ca2+ ionophores. Evidence for the role of protein phosphorylation in the activation of phospholipase A2 and independence from the Na+/H+ exchanger.
Banga, HS; Feinstein, MB; Halenda, SP; Lau, LF; Zavoico, GB, 1989
)
0.28
" The phosphorylation of pp63 and pp66, in particular, correlated with the mitogenic dose-response curve."( Mitogen-induced phosphorylation of human B-lymphocyte proteins. Relationship to protein kinase C activation.
Finney, M; Gordon, J; Guy, GR; Michell, RH, 1989
)
0.28
" The dose-response curves for triggering of O2- release and membrane depolarization by each of receptor-mediated agonists in phorbol myristate acetate-pretreated or control cells were identical."( Phorbol myristate acetate potentiates superoxide release and membrane depolarization without affecting an increase in cytoplasmic free calcium in human granulocytes stimulated by the chemotactic peptide, lectins and the calcium ionophore.
Kitagawa, S; Miura, Y; Ohsaka, A; Saito, M; Suzuki, I; Takaku, F, 1988
)
0.27
" The dose-response curves for 45Ca uptake and release were identical to those of the hormonally evoked [Ca2+]i increase."( Agonist-sensitive calcium pool in the pancreatic acinar cell. I. Permeability properties.
Fimmel, CJ; Muallem, S; Pandol, SJ; Schoeffield, MS, 1988
)
0.27
" Dose-response curves comparing 45Ca efflux and insulin secretion suggested that AA also stimulates hormone release by at least one other mechanism in addition to Ca2+ mobilization."( Exogenous arachidonic acid promotes insulin release from intact or permeabilized rat islets by dual mechanisms. Putative activation of Ca2+ mobilization and protein kinase C.
Metz, SA, 1988
)
0.27
" This difference in Ca2+/Mg2+ affinities was exploited in dose-response studies designed to determine which cation exerts primary control over K+/H+ exchange activity."( On the relative roles of Ca2+ and Mg2+ in regulating the endogenous K+/H+ exchanger of rat liver mitochondria.
Dordick, RS; Garlid, KD; Nakashima, RA, 1982
)
0.26
" Dose-response curves revealed that the antigen-presenting capacity of activated, MHC class II+, B7+ T cells was comparable to the one of B-LCL."( Antigen-presenting human T cells and antigen-presenting B cells induce a similar cytokine profile in specific T cell clones.
Frutig, K; Gallati, H; Limat, A; Mauri, D; Pichler, WJ; Pracht, I; Wyss-Coray, T, 1993
)
0.29
" The dose-response relationship for CCK-induced secretion is bell-shaped, with a characteristic supramaximal inhibition."( Supramaximal inhibition of cholecystokinin-induced pancreatic amylase release involves desensitization to cytoplasmic Ca2+.
Gylfe, E; Nilsson, J; Sjödin, L, 1994
)
0.29
" The dose-response for calcium release induced by sphingosine-1-phosphate correlated closely with the concentration required for stimulation of DNA synthesis."( Sphingosine-1-phosphate, a putative second messenger, mobilizes calcium from internal stores via an inositol trisphosphate-independent pathway.
Brooker, G; Mattie, M; Spiegel, S, 1994
)
0.29
" The dose-response curves showed that tyrosine phosphorylation and O2- release were stimulated in parallel by PMA, whereas tyrosine phosphorylation and an increase in [Ca2+]i, but not O2- release, were stimulated in parallel by FMLP or ionomycin."( Activation of the respiratory burst and tyrosine phosphorylation of proteins in human neutrophils: no direct relationship and involvement of protein kinase C-dependent and -independent signaling pathways.
Azuma, EK; Kitagawa, S; Mizoguchi, H; Saito, M; Takaku, F; Umezawa, K; Yuo, A, 1993
)
0.29
" This effect was dosage dependent, reaching a maximum at 10-microM ATP."( Purinergically induced membrane fluidization in ciliary cells: characterization and control by calcium and membrane potential.
Alfahel, E; Korngreen, A; Parola, AH; Priel, Z, 1996
)
0.29
" The slope and the shape of the dose-response curve of DEX were similar irrespective of either the input stimuli or the output cytokines; half-maximal inhibition was observed at 10(-8) mol/L, and nearly complete abolishment was observed at 10(-7) mol/L."( Glucocorticoids inhibit chemokine generation by human eosinophils.
Hirai, K; Izumi, S; Kasahara, T; Matsushima, K; Misaki, Y; Miyamasu, M; Morita, Y; Nakamura, H; Takaishi, T, 1998
)
0.3
" However, a higher gene dosage of the transgenic Bcl-2 was required for protection against Dex, compared to the PMA and/or ionomycin-induced apoptosis."( Biochemical and kinetic characterization of the glucocorticoid-induced apoptosis of immature CD4+CD8+ thymocytes.
Ivanov, VN; Nikolić-Zugić, J, 1998
)
0.3
" Western blotting confirmed that VT (50 to 1000 ng/ml) also significantly diminished GRP/BiP protein levels in a dose-response manner in PMA/ION-stimulated cells."( Down-regulation of the endoplasmic reticulum chaperone GRP78/BiP by vomitoxin (Deoxynivalenol).
Li, S; Pestka, JJ; Yang, GH, 2000
)
0.31
"1 mM)-stimulated AP accumulation, which was dose-dependently inhibited by higher concentrations of TPA with corresponding shifts in the dose-response curve for carbachol-stimulated AP accumulation."( Effects of phorbol ester treatment on dibutyryl cyclic adenosine-5' monophosphate- and carbachol-stimulated aminopyrine accumulation in isolated rat parietal cells.
Kopp, R; Pfeiffer, A, 2000
)
0.31
" Overexpression of NCS-1 caused a shift in the dose-response curve of inhibition of ATP-evoked secretion using phenylarsine oxide, an inhibitor of phosphatidylinositol 4-OH kinase (PI4K)."( Phosphatidylinositol 4-OH kinase is a downstream target of neuronal calcium sensor-1 in enhancing exocytosis in neuroendocrine cells.
Greenwood, S; Hilfiker, S; Jeromin, A; Rajebhosale, M; Vidugiriene, J, 2003
)
0.32
" Consistent with this, the Rho kinase inhibitors HA1077 and Y27632 inhibited both contraction and the 20-kDa myosin light chain phosphorylation induced by KCl as well as noradrenalin, with similar dose-response relations."( Ca2+-dependent activation of Rho and Rho kinase in membrane depolarization-induced and receptor stimulation-induced vascular smooth muscle contraction.
Sakurada, S; Sasaki, Y; Seto, M; Sugimoto, N; Takuwa, N; Takuwa, Y; Wang, Y, 2003
)
0.32
" This synergy may explain, at least in part, the steep dose-response relationship observed for CCh-induced TRPC6 currents expressed in HEK cells."( Activation of human TRPC6 channels by receptor stimulation.
Bahra, P; Estacion, M; Gosling, M; Li, S; Poll, C; Schilling, WP; Sinkins, WG; Westwick, J, 2004
)
0.32
" In addition, we found that LPA has no effect on neutrophil chemotaxis; however, it has stimulatory effects on neutrophil respiratory burst in a dose-response manner."( Lysophosphatidic acid triggers calcium entry through a non-store-operated pathway in human neutrophils.
Hauser, CJ; Itagaki, K; Kannan, KB, 2005
)
0.33
" Transfer of 3, 5, 10, or 23 million pure in vitro-activated T-cells accelerated diabetes onset in >90% of the recipients, with the degree of acceleration being dosage dependent."( In vivo control of diabetogenic T-cells by regulatory CD4+CD25+ T-cells expressing Foxp3.
Holm, TL; Hornum, L; Lundsgaard, D; Markholst, H, 2005
)
0.33
" Furthermore, particular cytokine levels were significantly decreased 2 h after drug dosing, compared with cytokine levels before dosing in mitogen-stimulated whole blood."( Cytokine analysis to predict immunosuppression.
Barten, MJ; Bocsi, J; Boldt, A; Dhein, S; Garbade, J; Gummert, JF; Mohr, FW; Rahmel, A, 2006
)
0.33
" ACh and Ca2+ dose-response studies demonstrated that NO3- solution does not shift their dose-response curves, and ATP depletion studies by dinitrophenol or anoxia demonstrated that exposure of NO3- solution prior to ATP depletion induced an enhanced initial phase followed by a sustained phase, whereas exposure of NO3- solution after ATP depletion induced only a sustained phase."( [Cl-]i modulation of Ca2+-regulated exocytosis in ACh-stimulated antral mucous cells of guinea pig.
Fujiwara, S; Kato, M; Katsu, K; Kubota, T; Nakahari, T; Shimamoto, C; Umegaki, E, 2007
)
0.34
" Preadipocytes of both species showed the same dose-response curves for the Ca(2+)-raise under thimerosal, and the mouse had two-fold higher kinetic constants for the Ca2+ ions entry."( [Comparative analysis of Ca(2+)-signalling in brown preadipocytes of ground squirrel Spermophillus undulatus and mouse].
Agafonova, TA; Bronnikov, GE; Dolgacheva, LP; Konakov, MV; Rybina, VV; Zinchenko, VP, 2007
)
0.34
" The significantly different dose-response relationships of IP(3)-mediated Ca(2+) release and CRAC channel activation indicate that I(CRAC) is activated by a functionally, and possibly physically, distinct sub-compartment of the endoplasmic reticulum (ER), the so-called CRAC store."( IP(3) receptor subtype-dependent activation of store-operated calcium entry through I(CRAC).
Beck, A; Fleig, A; Monteilh-Zoller, MK; Peinelt, C; Penner, R, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
calcium ionophorenull
[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
enolAlkenols; the term refers specifically to vinylic alcohols, which have the structure HOCR'=CR2. Enols are tautomeric with aldehydes (R' = H) or ketones (R' =/= H).
cyclic etherAny ether in which the oxygen atom forms part of a ring.
very long-chain fatty acidA fatty acid which has a chain length greater than C22. Very long-chain fatty acids which have a chain length greater than C27 are also known as ultra-long-chain fatty acids.
polyunsaturated fatty acidAny fatty acid containing more than one double bond. Acids in this group are reported to have cardioprotective effects; and levels are lowered in chronic fatigue syndrome.
[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]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID1127845Cytotoxicity against human M14 cells assessed as cell viability after 4 hrs using GF-AFC as substrate by ApoTox-Glo triplex assay2014Journal of medicinal chemistry, Feb-27, Volume: 57, Issue:4
Novel pyrrolidine diketopiperazines selectively inhibit melanoma cells via induction of late-onset apoptosis.
AID1231377Activity at human full length PPARgamma LBD transfected in COS7 cells assessed as transactivation activity by reporter gene assay relative to rosiglitazone2015Journal of medicinal chemistry, Jul-23, Volume: 58, Issue:14
Peroxisome Proliferator-Activated Receptor γ (PPARγ) and Ligand Choreography: Newcomers Take the Stage.
AID743734Activation of human recombinant DAGLalpha expressed in African green monkey COS7 cells assessed as increase in 2-arachidonoylglycerol level per mg of extracted lipid at 3 uM preincubated for 10 mins measured after 20 mins by LC-MS analysis (Rvb = 2.82 +/-2013European journal of medicinal chemistry, May, Volume: 63Biaryl tetrazolyl ureas as inhibitors of endocannabinoid metabolism: modulation at the N-portion and distal phenyl ring.
AID743735Activation of human recombinant DAGLalpha expressed in African green monkey COS7 cells assessed as increase in N-oleoylethanolamine level per mg of extracted lipid at 3 uM preincubated for 10 mins measured after 20 mins by LC-MS analysis (Rvb = 1.08 +/- 02013European journal of medicinal chemistry, May, Volume: 63Biaryl tetrazolyl ureas as inhibitors of endocannabinoid metabolism: modulation at the N-portion and distal phenyl ring.
AID1478483Cytotoxic activity against human HeLa cells at 1.47 uM by cytological profiling assay2017Journal of natural products, 03-24, Volume: 80, Issue:3
Naphthablins B and C, Meroterpenoids Identified from the Marine Sediment-Derived Streptomyces sp. CP26-58 Using HeLa Cell-Based Cytological Profiling.
AID1127844Induction of apoptosis human M14 cells assessed as caspase activity at 100 uM after 4 to 72 hrs using DEVD peptide as substrate by ApoTox-Glo triplex assay2014Journal of medicinal chemistry, Feb-27, Volume: 57, Issue:4
Novel pyrrolidine diketopiperazines selectively inhibit melanoma cells via induction of late-onset apoptosis.
AID1478481Cytotoxic activity against human HeLa cells at 0.295 uM by cytological profiling assay2017Journal of natural products, 03-24, Volume: 80, Issue:3
Naphthablins B and C, Meroterpenoids Identified from the Marine Sediment-Derived Streptomyces sp. CP26-58 Using HeLa Cell-Based Cytological Profiling.
AID716398Induction of apoptosis in malignant lymphocyte after 48 hrs2012Bioorganic & medicinal chemistry letters, Dec-01, Volume: 22, Issue:23
Polyether ionophores-promising bioactive molecules for cancer therapy.
AID743736Activation of human recombinant DAGLalpha expressed in African green monkey COS7 cells assessed as increase in anandamide level per mg of extracted lipid at 3 uM preincubated for 10 mins measured after 20 mins by LC-MS analysis (Rvb = 0.16 +/- 004 pmol)2013European journal of medicinal chemistry, May, Volume: 63Biaryl tetrazolyl ureas as inhibitors of endocannabinoid metabolism: modulation at the N-portion and distal phenyl ring.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (4,298)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990522 (12.15)18.7374
1990's2057 (47.86)18.2507
2000's1152 (26.80)29.6817
2010's494 (11.49)24.3611
2020's73 (1.70)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 6.42

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 Index6.42 (24.57)
Research Supply Index8.39 (2.92)
Research Growth Index4.81 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (6.42)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials10 (0.23%)5.53%
Reviews27 (0.62%)6.00%
Case Studies9 (0.21%)4.05%
Observational3 (0.07%)0.25%
Other4,336 (98.88%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]