CHEBI:63954 - ionomycin

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ChEBI Name ionomycin
ChEBI ID CHEBI:63954
Definition 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 Ca2+ and as a research tool to understand Ca2+ transport across biological membranes.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5380046, eMolecules:27515014, ZINC000169289396
Download Molfile XML SDF
Formula C41H72O9
Net Charge 0
Average Mass 709.00500
Monoisotopic Mass 708.51763
InChI InChI=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
InChIKey PGHMRUGBZOYCAA-ADZNBVRBSA-N
SMILES [H][C@]1(CC[C@](C)(O1)[C@@]1([H])CC[C@](C)(O1)[C@@H](C)O)C[C@H](O)[C@H](C)[C@H](O)[C@H](C)\C=C\C[C@@H](C)C[C@@H](C)C(\O)=C\C(=O)[C@@H](C)C[C@@H](C)C[C@H](C)CCC(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
calcium ionophore

View more via ChEBI Ontology
ChEBI Ontology
Outgoing ionomycin (CHEBI:63954) has role calcium ionophore (CHEBI:22986)
ionomycin (CHEBI:63954) has role metabolite (CHEBI:25212)
ionomycin (CHEBI:63954) is a cyclic ether (CHEBI:37407)
ionomycin (CHEBI:63954) is a enol (CHEBI:33823)
ionomycin (CHEBI:63954) is a polyunsaturated fatty acid (CHEBI:26208)
ionomycin (CHEBI:63954) is a very long-chain fatty acid (CHEBI:27283)
IUPAC Name
(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
Manual Xref Database
US3873693 Patent
View more database links
Registry Numbers Types Sources
3642126 Reaxys Registry Number Reaxys
56092-81-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
20 February 2012