Basic information
- CAS
52665-69-7- Standard SMILES
CNc1ccc2oc(C[C@@H]3OC4(CC[C@@H]3C)O[C@H](C(C)C(=O)c3ccc[nH]3)[C@H](C)C[C@H]4C)nc2c1C(=O)O- InChIKey
HIYAVKIYRIFSCZ-CVXKHCKVSA-N- Molecular formula
- C29H37N3O6
- Average molar mass
- 523.6 g/mol
- Monoisotopic mass
- 523.26823591
Overview
Calcimycin is an aminobenzoic acid.
Names & identifiers
- Preferred name
- Ionophore A23187
- IUPAC
- 5-(methylamino)-2-[[(2S,3R,5R,8S,9S)-3,5,9-trimethyl-2-[1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid
- English name
- A23187
- Molecular formula
- C29H37N3O6
- Molecular weight
- 523.62
Names & synonyms
Ionophore A231875-(methylamino)-2-(((2S,3R,5R,8S,9S)-3,5,9-trimethyl-2-(1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl)-1,7-dioxaspiro(5.5)undecan-8-yl)methyl)-1,3-benzoxazole-4-carboxylic acid5-(methylamino)-2-[[(2S,3R,5R,8S,9S)-3,5,9-trimethyl-2-[1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acidRefChem:1087417Calcium ionophore A23187MFCD00151202Spectrum_001976A23187 free acidUPCMLD-DP093CBiol_001742BSPBio_001576KBioGR_000296
Show more names
SBE-β-CDCALCIMYCINA23187, 98%, FREE ACID5-(Methylamino)-2-[[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)-ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-4-benzoxazolecarboxylic acid11B1A23187(R*),9B2Calimycin(2S*,3S*),8B2
KBioSS_000296KBioSS_002542DivK1c_000618SCHEMBL258988CHEBI:3305CHEMBL1434752UPCMLD-DP093:001UPCMLD-DP093:002
Properties
Computed structural properties
- XLogP
- 5.9
- Topological polar surface area
- 127 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 7
- Heavy atoms
- 38
- Formal charge
- 0
- Complexity
- 873
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Physicochemical properties
- Melting point
- 187 · 187-190 °C
- alpha
- 25 · D25 -56° (c = 1 in chloroform)
- Boiling point
- 710.3 · 710.3±55.0 °C(Predicted)
- Density
- 1.28 · 1.28±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in DMSO with warming or sonication. Also soluble in ethanol or ethyl acetate
- form
- Solid
- pka
- 1 · pKa1 6.9 in 90% DMSO
- color
- white to light yellow
- Merck
- 13 · 13,1639
- BRN
- 1096801 · 1096801
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 4 months.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 8
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- DM4676000
- hs_code
- 29349990
- Toxicity
- LD50 i.p. in mice: 10 mg/kg (Gale)
- risk_code
- 36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Applications
DescriptionAntibiotic A-23187 (52665-69-7) is a highly selective divalent cation ionophore, commonly used to increase intracellular Ca2+ levels in intact cells (though it is most selective for Mn2+).1 It uncouples oxidative phosphorylation.2 In addition, antibiotic A-23187 inhibits ATPase activity.3
UsesCalcimycin is a potent calcium ionophore isolated from Streptomyces chartreusis in 1974. Calcimycin is a spiroketal substituted by pyrollic and benzoxazolyl groups which afford its high affinity and selectivity for calcium. Calimycin exhibits broad biological activity against bacteria, fungi and protozoa. It has found wide application as a research tool for calcium-regulated cellular events.
UsesA23187 (Mixed Calcium-Magnesium Salt) is used in cell activation experiments when calcium dose-response data are not required. Ca-Mg ratio ~ 1:1. it is widely used as a compound in cell activation. It is used as a highly selective Ca2+ ionophore. it is used in studies of intracellular Ca2+ mediated events. A23187 has been observed to induce cell activation, differentiation or proliferation. In vitro experimentation has shown A23187 to boost ROS generation and platelet fragmentation. A23187 is a widely used ionophore. It has the ability to increase the intracellular concentrations of cations and is widely used to increase the intracellular levels of calcium. Visualization of Synaptic Ca2+ Calmodulin-Dependent Protein Kinase II Activity in Living Neurons.
UsesCA was used in elucidating the mechanisms underlying the positive and inotropic and chronotropic ability of CA on isolated superfused guinea pig atria. It may also be used to stimulate and measure the erythrocyte Ca2+ dependent K+ channels as the K+ efflux.
General DescriptionA mobile ion-carrier that forms stable complexes with divalent cations. Useful for increasing intracellular Ca2+ levels. Also acts as an uncoupler of oxidative phosphorylation and inhibitor of mitochondrial ATPase activity. An antibiotic with weak activity against Gram-positive bacteria. Also induces apoptosis in mouse lymphoma cell line (S49); however, A23187 has been shown to block apoptosis in other systems, such as when interleukin-3 (IL-3) is withdrawn from IL-3-dependent cells.
Upstream & downstream products
Upstream raw materials
Related reactions
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Compound notes
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