[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-carbonyloxy]magnesio 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-carboxylate

• ChemBase ID: 133782
• Molecular Formular: C58H72MgN6O12
• Molecular Mass: 1069.53028
• Monoisotopic Mass: 1068.50586347
• 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)ccc(c2C(=O)O[Mg]OC(=O)c1c(ccc2c1nc(o2)C[C@@H]1[C@@H](CC[C@@]2(O1)[C@@H](C[C@H]([C@H](O2)[C@H](C)C(=O)c1ccc[nH]1)C)C)C)NC)NC
• Canonical SMILES: CNc1ccc2c(c1C(=O)O[Mg]OC(=O)c1c(NC)ccc3c1nc(o3)C[C@H]1O[C@@]3(CC[C@H]1C)O[C@@H]([C@@H](C[C@H]3C)C)[C@@H](C(=O)c1ccc[nH]1)C)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/2C29H37N3O6.Mg/c2*1-15-10-11-29(17(3)13-16(2)27(38-29)18(4)26(33)20-7-6-12-31-20)37-22(15)14-23-32-25-21(36-23)9-8-19(30-5)24(25)28(34)35;/h2*6-9,12,15-18,22,27,30-31H,10-11,13-14H2,1-5H3,(H,34,35);/q;;+2/p-2/t2*15-,16-,17-,18-,22-,27+,29+;/m11./s1
• InChIKey: XBWKBTZDBYFEMH-UIOMRPQBSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: [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-carbonyloxy]magnesio 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-carboxylate
• IUPAC Traditional name: [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-carbonyloxy]magnesio 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-carboxylate
• Synonyms: A23187; Antibiotic A 23187; Calcimycin hemimagnesium salt; Calcium Ionophore A23187 hemimagnesium salt; Calimycin 半镁盐; Calcium Ionophore A23187

Database IDs

• CAS Number: 72124-77-7
• MDL Number: MFCD00151203
• Beilstein Number: 6765085
• PubChem SID: 162228059; 24893158
• PubChem CID: 16219184

CALCULATED PROPERTIES

• Acid pKa: 13.657998
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): 10.97132
• LogD (pH = 7.4): 10.971597
• Log P: 10.9716
• Molar Refractivity: 283.4888 cm^3
• Polarizability: 113.51107 Å^3
• Polar Surface Area: 231.36 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

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

DETAILS

Sigma Aldrich - C9400

Application
Ionophore highly selective for Ca2+. Potentiates responses to NMDA but not quisqualate. In cell culture, stimulates nitric oxide production by calmodulin-dependent constitutive nitric oxide synthase. Used to study effects of elevated intracellular calcium on mitochondrial function and intrinsic apoptosis.