(7R,9S,11S)-14-[(2R,4R,8R,9R,10S,11S)-9,11-dihydroxy-12-[(2S,5S)-5-[(2R,5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,8,10-trimethyldodec-6-en-2-yl]-7,9,11-trimethyl-1,3-dioxa-2-calcacyclotetradec-13-ene-4,12-dione

• ChemBase ID: 153847
• Molecular Formular: C41H70CaO9
• Molecular Mass: 747.0671
• Monoisotopic Mass: 746.4645748
• SMILES: C[C@H]1CCC(=O)O[Ca]O/C(=C\C(=O)[C@H](C[C@H](C1)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]1CC[C@@](O1)(C)[C@@H](C)O)O)O
• Canonical SMILES: C[C@@H](C[C@H](/C/1=C/C(=O)[C@@H](C)C[C@@H](C)C[C@H](CCC(=O)O[Ca]O1)C)C)C/C=C/[C@H]([C@H]([C@H]([C@H](C[C@@H]1CC[C@@](O1)(C)[C@H]1CC[C@@](O1)(C)[C@H](O)C)O)C)O)C
• InChI: InChI=1S/C41H72O9.Ca/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);/q;+2/p-2/t25-,26-,27+,28-,29-,30+,31+,32-,33+,36+,37-,39-,40+,41+;/m1./s1
• InChIKey: WKRWUYKLUMMAKG-LTYVSVOXSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: (7R,9S,11S)-14-[(2R,4R,8R,9R,10S,11S)-9,11-dihydroxy-12-[(2S,5S)-5-[(2R,5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,8,10-trimethyldodec-6-en-2-yl]-7,9,11-trimethyl-1,3-dioxa-2-calcacyclotetradec-13-ene-4,12-dione
• IUPAC Traditional name: (7R,9S,11S)-14-[(2R,4R,8R,9R,10S,11S)-9,11-dihydroxy-12-[(2S,5S)-5-[(2R,5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,8,10-trimethyldodec-6-en-2-yl]-7,9,11-trimethyl-1,3-dioxa-2-calcacyclotetradec-13-ene-4,12-dione
• Synonyms: Ionomycin calcium salt; Ionomycin calcium salt from Streptomyces conglobatus; Ionomycin caicium salt 钙盐

Database IDs

• CAS Number: 56092-82-1
• EC Number: 200-664-3
• MDL Number: MFCD00083634
• Beilstein Number: 1416163
• PubChem SID: 162247986
• PubChem CID: 71311740

CALCULATED PROPERTIES

• Acid pKa: 14.007372
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 5.6708
• LogD (pH = 7.4): 5.6707997
• Log P: 5.6708
• Molar Refractivity: 198.3516 cm^3
• Polarizability: 80.97051 Å^3
• Polar Surface Area: 131.75 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: 188.6 °F; 87 °C

Safety Information

• RTECS: NO0650000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1; 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C

Product Information

• Purity: ≥80% (HPLC); ≥98% (HPLC)
• Concentration: 1 mM in DMSO
• Biological Source: from Streptomyces conglobatus
• Sterility: 0.2 μm filtered
• Quality Level: PREMIUM
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C41H70CaO9

DETAILS

Sigma Aldrich - I3909

Frequently Asked Questions
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Application
Ionomycin is an ionophore produced by the bacterium Streptomyces conglobatus. It has been shown to induce central demyelination 1, inhibit adrenal bovine TREK-1 channels 2, and to regulate cell division of mature human B cells 3. It is used to study the effects of calcium flux on endoplasmic reticulum (ER) stress, mitochodrial stress and intrinsic apoptosis mechanisms. It is also used to stimulate the intracellular production of the cytokines, interferon, perforin, IL-2, and IL-4 usually in conjunction with PMA. Product I3909 is a Ready Made Solution, from Streptomyces conglobatus. The concentration is 1 Mm in DMSO and it is 0.2 μm filtered.
Biochem/physiol Actions
Ca2+ ionophore that is more effective than A23187 as a mobile ion carrier for Ca2+; non-fluorescent; used to study Ca2+ transport across biological membranes; induces apoptotic degeneration of embryonic cortical neurons.
Ionomycin is a Ca2+ ionophore that is more effective than A23187 as a mobile ion carrier for Ca2+. It is non-fluorescent. It induces apoptotic degeneration of embryonic cortical neurons, induces central demyelination 1 and inhibits adrenal bovine TREK-1 channels2.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 58168

Other Notes
Nonfluorescent ionophoric antibiotic which exhibits a greater selectivity for Ca2+ over Mg2+ than does A231871,2,3
Biochem/physiol Actions
Ca2+ ionophore that is more effective than A23187 as a mobile ion carrier for Ca2+; non-fluorescent; used to study Ca2+ transport across biological membranes; induces apoptotic degeneration of embryonic cortical neurons.