6-bromo-5-(methylamino)-2-{[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-1,3-benzoxazole-4-carboxylic acid

• ChemBase ID: 134400
• Molecular Formular: C29H36BrN3O6
• Molecular Mass: 602.51664
• Monoisotopic Mass: 601.17874789
• SMILES: C[C@@H]1CC[C@]2([C@@H](C[C@H]([C@H](O2)[C@H](C)C(=O)c2ccc[nH]2)C)C)O[C@@H]1Cc1nc2c(o1)cc(c(c2C(=O)O)NC)Br
• Canonical SMILES: CNc1c(Br)cc2c(c1C(=O)O)nc(o2)C[C@H]1O[C@@]2(CC[C@H]1C)O[C@@H]([C@@H](C[C@H]2C)C)[C@@H](C(=O)c1ccc[nH]1)C
• InChI: InChI=1S/C29H36BrN3O6/c1-14-8-9-29(16(3)11-15(2)27(39-29)17(4)26(34)19-7-6-10-32-19)38-20(14)13-22-33-25-21(37-22)12-18(30)24(31-5)23(25)28(35)36/h6-7,10,12,14-17,20,27,31-32H,8-9,11,13H2,1-5H3,(H,35,36)/t14-,15-,16-,17-,20-,27+,29+/m1/s1
• InChIKey: LDXQFZZGVTWFCF-FHYGWRBKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-bromo-5-(methylamino)-2-{[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-1,3-benzoxazole-4-carboxylic acid
• IUPAC Traditional name: 6-bromo-5-(methylamino)-2-{[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-1,3-benzoxazole-4-carboxylic acid
• Synonyms: 4-Bromo-A23187; 4-Bromo-calcimycin; 4-Bromo-calcium Ionophore A23187

Database IDs

• CAS Number: 76455-48-6
• MDL Number: MFCD00077667
• PubChem SID: 24891982; 162228676; 24850144
• PubChem CID: 16211362

CALCULATED PROPERTIES

• Acid pKa: 0.6309237
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 3.3317478
• LogD (pH = 7.4): 2.6449296
• Log P: 5.6139774
• Molar Refractivity: 150.2948 cm^3
• Polarizability: 58.61695 Å^3
• Polar Surface Area: 126.68 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble20 mg/mL; ethanol: soluble20 mg/mL, clear, yellow
• Apperance: yellow powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (N)
• Empirical Formula (Hill Notation): C29H36BrN3O6

DETAILS

Sigma Aldrich - 16569

Application
Nonfluorescent Ca2+ ionophore that can be used to calibrate the quantitation of cytoplasmic free Ca2+ with fluorescent probes.
Bromo-A23187, a nonfluorescent ionophore, has been used in photolysis of a caged-Ca2+ compound and in [Ca2+]i elevation protocols1. It can be used to calibrate the quantitation of cytoplasmic free Ca2+ with fluorescent probes.
Other Notes
In biological environment, bromo-A23187 has a higher selectivity for Ca2+ over Mg2+ than A231872
Biochem/physiol Actions
Ionophores disrupt transmembrane ion concentration gradients which are required for proper functioning and survival of microorganisms. An ionophore, such as Bromo-A23187, increases the permeability of biological membranes to calcium.

Sigma Aldrich - B7272

Application
Nonfluorescent Ca2+ ionophore that can be used to calibrate the quantitation of cytoplasmic free Ca2+ with fluorescent probes.
Biochem/physiol Actions
Ca2+ ionophore that is used to potentiate responses to NMDA, but not quisqualate.
Other Notes
Analog of calcium ionophore A23187