5-(methylamino)-2-({3,9,11-trimethyl-8-[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: 103588
• Molecular Formular: C29H37N3O6
• Molecular Mass: 523.62058
• Monoisotopic Mass: 523.26823592
• SMILES: CNc1c(C(=O)O)c2c(oc(CC3OC4(CCC3C)OC(C(C)CC4C)C(C)C(=O)c3ccc[nH]3)n2)cc1
• Canonical SMILES: CNc1ccc2c(c1C(=O)O)nc(o2)CC1OC2(CCC1C)OC(C(CC2C)C)C(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)
• InChIKey: HIYAVKIYRIFSCZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(methylamino)-2-({3,9,11-trimethyl-8-[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: calcimycin
• Synonyms: Calcium Ionophore A23187; ANTIBIOTIC A23187

Database IDs

• CAS Number: 52665-69-7
• EC Number: 258-084-1
• PubChem SID: 162091333
• PubChem CID: 1959

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

• Melting Point: 186°C

Safety Information

• Storage Condition: -20°C
• RTECS: DM4676000
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39

DETAILS

MP Biomedicals - 02152328

Free Acid
White crystalline solid.
Antibiotic A23187 is an antibiotic which demonstrates weak in vitro activity against gram-positive bacteria and fungi. It also has the ability to form stable complexes with divalent cations, increasing their ability to cross biological membranes, thus giving A23187 properties as an ionophore. Its U.V. and fluorescence spectral properties allow this calcium ionophore to be useful as a cytoplasmic free calcium ion probe. A23187 does exhibit toxicity and is a potential health hazard, so caution should be used when handling, in accordance with normal procedures for handling toxic compounds.