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: 125569
• Molecular Formular: C29H37N3O6
• Molecular Mass: 523.62058
• Monoisotopic Mass: 523.26823592
• SMILES: O=C(O)c1c(NC)ccc2oc(nc12)C[C@H]1O[C@]2(O[C@@H]([C@H](C)C[C@H]2C)[C@@H](C(=O)c2ccc[nH]2)C)CC[C@H]1C
• Canonical SMILES: CNc1ccc2c(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/C29H37N3O6/c1-15-10-11-29(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/h6-9,12,15-18,22,27,30-31H,10-11,13-14H2,1-5H3,(H,34,35)/t15-,16-,17-,18-,22-,27+,29+/m1/s1
• InChIKey: HIYAVKIYRIFSCZ-CYEMHPAKSA-N

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-carboxylic acid
• 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-carboxylic acid
• Synonyms: A23187; Calcium Ionophore A23187; Antibiotic A 23187; Calimycin; Calcium Ionophore A23187; Calcium ionophore III; 抗生素 A 23187; 钙离子载体; 钙离子载体 A23187; 钙离子载体 A23187; 钙离子载体 III

Database IDs

• CAS Number: 52665-69-7
• EC Number: 258-084-1
• MDL Number: MFCD00151202
• Beilstein Number: 1096801
• PubChem SID: 24852712; 24277964; 162219919
• PubChem CID: 11957499
• CHEMBL: 1256686
• Chemspider ID: 10131749
• Wikipedia Title: A23187

CALCULATED PROPERTIES

• Acid pKa: -0.7834525
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 2.7492297
• LogD (pH = 7.4): 1.8907063
• Log P: 4.366499
• Molar Refractivity: 142.672 cm^3
• Polarizability: 55.82371 Å^3
• Polar Surface Area: 126.68 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble50 mg/mL (with heating or sonication. Solutions are stable for at least 3 months at -20 °C when protected from light and water contamination.); ethanol: soluble5 mg/mL (with heating. Solutions are stable for at least 3 months at -20 °C when protected from light and water contamination.)
• Apperance: white to light yellow powder
• Melting Point: 187-190 °C

Safety Information

• RTECS: DM4676000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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: ~95% (HPLC); ≥98% (TLC)
• Grade: Selectophore™
• Quality Level: PREMIUM
• Quality: function tested
• Empirical Formula (Hill Notation): C29H37N3O6

DETAILS

Sigma Aldrich - C7522

Application
高选择性钙离子载体增强对 NMDA 非使君子氨酸的响应。在细胞培养中，通过钙调素依赖结构型一氧化氮合酶刺激一氧化氮的生成。

Sigma Aldrich - 21186

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.
General description
Visit our Sensor Applications portal to learn more.
Other Notes
Preparation of an optical chemical sensor for Ca2+ and Mg2+,1
Legal Information
Selectophore is a trademark of Sigma-Aldrich GmbH

Sigma Aldrich - 21045

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.
Other Notes
A23187 increases the permeability of biological membranes with a high selectivity for Ca2+. It is used extensively in studies related to intracellular Ca2+,1,2,3