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CHEBI:63954 - ionomycin

ChEBI IDCHEBI:63954
ChEBI Nameionomycin
Stars
DefinitionA 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.
Last Modified20 February 2012
SubmitterGareth Owen
DownloadsMolfile
FormulaC41H72O9
Net Charge0
Average Mass709.018
Monoisotopic Mass708.51763
SMILES[H][C@@]1(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)CC[C@@](C)([C@@]2([H])CC[C@@](C)([C@@H](C)O)O2)O1
InChIInChI=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
InChIKeyPGHMRUGBZOYCAA-ADZNBVRBSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
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 XrefsDatabases
US3873693Patent
Registry NumbersSources
Reaxys:3642126Reaxys
CAS:56092-81-0ChemIDplus
Citations