:Ionomycin

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 400118302

| ImageFile=Ionomycin (free acid).svg

| ImageSize=300

| IUPACName=(4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-19,21-Dihydroxy-22-{(2S,2{{prime}}R,5S,5{{prime}}S)-5{{prime}}-[(1R)-1-hydroxyethyl]-2,5{{prime}}-dimethyloctahydro-2,2{{prime}}-bifuran-5-yl}-4,6,8,12,14,18,20-heptamethyl-11-oxido-9-oxodocosa-10,16-dienoic acid

| OtherNames=

|Section1={{Chembox Identifiers

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 501617

| ChEMBL2_Ref = {{ebicite|changed|EBI}}

| ChEMBL2 = 1222121

| PubChem = 6912226

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 5288579

| SMILES = C[C@H](CCC(=O)O)C[C@H](C)C[C@H](C)C(=O)/C=C(/[C@H](C)C[C@H](C)C/C=C/[C@@H](C)[C@H]([C@@H](C)[C@H](C[C@@H]1CC[C@@](O1)(C)[C@H]2CC[C@@](O2)(C)[C@@H](C)O)O)O)\O

| InChI = 1/C41H72O9/c1-25(21-29(5)34(43)24-35(44)30(6)22-27(3)20-26(2)14-15-38(46)47)12-11-13-28(4)39(48)31(7)36(45)23-33-16-18-41(10,49-33)37-17-19-40(9,50-37)32(8)42/h11,13,24-33,36-37,39,42-43,45,48H,12,14-23H2,1-10H3,(H,46,47)/b13-11+,34-24-/t25-,26-,27+,28-,29-,30+,31+,32-,33+,36+,37-,39-,40+,41+/m1/s1

| InChIKey = PGHMRUGBZOYCAA-ADZNBVRBBY

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C41H72O9/c1-25(21-29(5)34(43)24-35(44)30(6)22-27(3)20-26(2)14-15-38(46)47)12-11-13-28(4)39(48)31(7)36(45)23-33-16-18-41(10,49-33)37-17-19-40(9,50-37)32(8)42/h11,13,24-33,36-37,39,42-43,45,48H,12,14-23H2,1-10H3,(H,46,47)/b13-11+,34-24-/t25-,26-,27+,28-,29-,30+,31+,32-,33+,36+,37-,39-,40+,41+/m1/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = PGHMRUGBZOYCAA-ADZNBVRBSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 56092-81-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 54V905V6AT

}}

|Section2={{Chembox Properties

| C=41 | H=72 | O=9

| MolarMass=709.0050 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| SolubleOther=insoluble in water, soluble in fats, DMSO, heptane and hexane

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

Ionomycin is an ionophore and an antibiotic that binds calcium ions (Ca²⁺) in a ratio 1:1. It is produced by the bacterium Streptomyces conglobatus.{{Cite journal|display-authors=etal|vauthors=Lautens M|date=2002|title=Total synthesis of ionomycin using ring-opening strategies|journal=Organic Letters|volume=4|issue=11|pages=1879–1882|doi=10.1021/ol025872f|pmid=12027637|issn=1523-7060}} It binds also other divalent cations like magnesium and cadmium, but binds Ca²⁺ preferably.{{Cite journal|display-authors=et al|vauthors=Kao J|date=2010|title=Practical aspects of measuring intracellular calcium signals with fluorescent indicators|url=https://www.sciencedirect.com/science/article/pii/B9780123748416000050|journal=Methods in Cell Biology|volume=99|pages=113–152|doi=10.1016/B978-0-12-374841-6.00005-0|issn=0091-679X|pmid=21035685|isbn=9780123748416}}{{Cite journal|display-authors=etal|vauthors=Toeplitz BK|date=1979|title=Structure of ionomycin - a novel diacidic polyether antibiotic having high affinity for calcium ions|url=https://pubs.acs.org/doi/10.1021/ol025872f|journal=Journal of the American Chemical Society|volume=101|issue=12|pages=3344–3353|doi=10.1021/ja00506a035|issn=0002-7863}}

It has 14 chiral centers. Its β-diketone and carboxylic acid group form a chelate with calcium.

It was extracted in 1978 and the complete structure was described in 1979.

It is used in research to raise the intracellular calcium level (Ca²⁺) and as a research tool to understand Ca²⁺ transport across biological membranes.

Ionomycin is often sold as a free acid, or as a Ca²⁺ salt. Both are insoluble in water, but soluble in fats and DMSO. Because of their fat solubility, they bind to proteins like albumin, which may interfere with their use in studies involving blood.