[5-(methylamino)-2-{[(2R,3R,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]calcio 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: 132391
• Molecular Formular: C58H72CaN6O12
• Molecular Mass: 1085.30328
• Monoisotopic Mass: 1084.48341275
• 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[Ca]OC(=O)c1c(ccc2c1nc(o2)C[C@@H]1[C@@H](CCC2(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[Ca]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]1OC2(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.Ca/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/t15-,16-,17-,18-,22-,27+,29?;15-,16-,17-,18-,22-,27+,29+;/m11./s1
• InChIKey: LAQWEYASNNRUGY-PLYBNSMSSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: [5-(methylamino)-2-{[(2R,3R,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]calcio 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,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]calcio 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: Antibiotic A 23187; Calcimycin hemicalcium salt; Calimycin; Calcium Ionophore A23187 hemicalcium salt; A23187 hemicalcium salt; Antibiotic A 23187 hemicalcium salt; Calimycin hemicalcium salt; A23187 半钙盐; 钙离子载体 A23187 半钙盐

Database IDs

• CAS Number: 59450-89-4
• MDL Number: MFCD00077678
• Beilstein Number: 6765084
• PubChem SID: 24893145; 162226668
• PubChem CID: 16219182

CALCULATED PROPERTIES

• Acid pKa: 13.657998
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): 11.271446
• LogD (pH = 7.4): 11.271598
• Log P: 11.2716
• Molar Refractivity: 283.4888 cm^3
• Polarizability: 114.048065 Å^3
• Polar Surface Area: 231.36 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: acetone: soluble10 mg/mL, clear, faintly yellow-green; DMSO: soluble; ethanol: soluble
• Apperance: yellow powder

Safety Information

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

Product Information

• Purity: ≥98.0% (TLC)
• Impurities: ≤2% water
• Empirical Formula (Hill Notation): C29H36Ca0.5N3O6

DETAILS

Sigma Aldrich - C9275

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.

Sigma Aldrich - 21046

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.