(4R,6S,8S,12R,14R,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

• ChemBase ID: 153810
• Molecular Formular: C41H72O9
• Molecular Mass: 709.00498
• Monoisotopic Mass: 708.51763388
• 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]1CC[C@@](O1)(C)[C@@H](C)O)O)O)\O
• Canonical SMILES: C[C@@H](C[C@H](/C(=C/C(=O)[C@H](C[C@H](C[C@@H](CCC(=O)O)C)C)C)/O)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/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)/t25-,26-,27+,28-,29-,30+,31+,32-,33+,36+,37-,39-,40+,41+/m1/s1
• InChIKey: PGHMRUGBZOYCAA-WZUHJRNWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,6S,8S,12R,14R,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
• IUPAC Traditional name: (4R,6S,8S,12R,14R,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
• Synonyms: Ionomycin from Streptomyces conglobatus

Database IDs

• CAS Number: 56092-81-0
• MDL Number: MFCD06798385
• Beilstein Number: 3642126
• PubChem SID: 162247949; 24896159
• PubChem CID: 6912226

CALCULATED PROPERTIES

• Acid pKa: 4.797804
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 6.410153
• LogD (pH = 7.4): 4.617693
• Log P: 7.1905427
• Molar Refractivity: 200.4936 cm^3
• Polarizability: 78.755554 Å^3
• Polar Surface Area: 153.75 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: NO0600000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 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
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C41H72O9

DETAILS

Sigma Aldrich - I9657

Application
Ionomycin is an ionophore produced by the bacterium Streptomyces conglobatus. It has been shown to induce central demyelination , inhibit adrenal bovine TREK-1 channels , and to regulate cell division of mature human B cells . 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.
Biochem/physiol Actions
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 and inhibits adrenal bovine TREK-1 channels.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information