(7R,9S,11S,13Z)-14-[(2R,4R,6E,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: 134308
• 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/b13-11+,34-24-;/t25-,26-,27+,28-,29-,30+,31+,32-,33+,36+,37-,39-,40+,41+;/m1./s1
• InChIKey: WKRWUYKLUMMAKG-WYGBAUISSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: (7R,9S,11S,13Z)-14-[(2R,4R,6E,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,13Z)-14-[(2R,4R,6E,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 from Streptomyces conglobatus

Database IDs

• CAS Number: 56092-82-1
• MDL Number: MFCD00083634
• Beilstein Number: 1416163
• PubChem SID: 162228585
• PubChem CID: 71308788

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

• Solubility: DMSO: soluble10 mg/mL; ethanol: soluble
• Apperance: white to off-white powder

Safety Information

• Storage Condition: desiccated; protect from light
• RTECS: NO0650000
• 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: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - I0634

Preparation Note
Store ionomycin in powder form desiccated and protected from light at 2-8 °C. Under these conditions the product is stable for 3 years. Store stock solutions in ethanol or DMSO at -20 °C, protected from light. Under these conditions the stock solutions are stable for several months. For short term use (up to 6 weeks) the stock solutions maybe stored at 2-8 °C protected from light.
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.