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Calcimycin

CAT: 0804-HY-N6687-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N6687-02Size:5 mg
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Description
Calcimycin (A-23187) is an antibiotic and a unique divalent cation ionophore (like calcium and magnesium) . Calcimycin induces Ca2+-dependent cell death by increasing intracellular calcium concentration. Calcimycin inhibits the growth of Gram-positive bacteria and some fungi. Calcimycin also inhibits the activity of ATPase and uncouples oxidative phosphorylation (OXPHOS) of mammalian cells. Calcimycin induces apoptosis and autophagy[1][2][3][4][5].
CAS Number
52665-69-7
Product Name Alternative
A-23187; Antibiotic A-23187
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Antibiotic; Apoptosis; Autophagy; Bacterial; Fungal; Oxidative Phosphorylation
Type
Natural Products
Related Pathways
Anti-infection; Apoptosis; Autophagy; Metabolic Enzyme/Protease
Applications
Cancer-Kinase/protease
Field of Research
Cancer; Infection; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/calcimycin.html
Concentration
10mM
Purity
99.12
Solubility
DMSO : 33.33 mg/mL (ultrasonic)
Smiles
O=C(C1=C2N=C(C[C@H]3O[C@]4(O[C@H]([C@H](C)C(C5=CC=CN5)=O)[C@H](C)C[C@H]4C)CC[C@H]3C)OC2=CC=C1NC)O
Molecular Formula
C29H37N3O6
Molecular Weight
523.62
Precautions
H302, H315, H319, H335
References & Citations
[1]Wu Q, et al. Characterization of the biosynthesis gene cluster for the pyrrole polyether antibiotic calcimycin (A23187) in Streptomyces chartreusis NRRL 3882. Antimicrob Agents Chemother. 2011 Mar;55 (3) :974-82.|[2]Elliott JI, et al. IKCa1 activity is required for cell shrinkage, phosphatidylserine translocation and death in Tlymphocyte apoptosis. EMBO Rep. 2003 Feb;4 (2) :189-94.|[3]Engedal N, et al. Modulation of intracellular calcium homeostasis blocks autophagosome formation. Autophagy. 2013 Oct;9 (10) :1475-90.|[4]Mawatwal S, et al. Calcimycin mediates mycobacterial killing by inducing intracellular calcium-regulated autophagy in a P2RX7 dependent manner. Biochim Biophys Acta Gen Subj. 2017 Dec;1861 (12) :3190-3200.|[5]Wang JP, et al. Effect of norathyriol, isolated from Tripterospermum lanceolatum, on A23187-induced pleurisy and analgesia in mice. Naunyn Schmiedebergs Arch Pharmacol. 1994 Jul;350 (1) :90-5.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, sealed storage, away from moisture)
Scientific Category
Natural Products
Clinical Information
Phase 4

Chemical Information

Calcimycin

5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-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 is a benzoxazole.

CAS Number52665-69-7
PubChem CID11957499
IUPAC Name5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-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
Molecular FormulaC29H37N3O6
Molecular Weight523.6
XLogP5.9
Topological Polar Surface Area127
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count7
Heavy Atom Count38
Formal Charge0
Complexity873
SMILES
C[C@@H]1CC[C@]2([C@@H](C[C@H]([C@H](O2)[C@H](C)C(=O)C3=CC=CN3)C)C)O[C@@H]1CC4=NC5=C(O4)C=CC(=C5C(=O)O)NC
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
Chemical Structure
2D Structure
2D structure of Calcimycin
CAS: 52665-69-7
CID: 11957499
Formula: C29H37N3O6
MW: 523.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight523.6
XLogP35.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count7
Exact Mass523.26823591
Monoisotopic Mass523.26823591
Topological Polar Surface Area127 Ų
Heavy Atom Count38
Formal Charge0
Complexity873
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
C160-1MGCalcimycin
T75656-01Calcimycin hemimagnesium
CST 23911SA23187 (Calcimycin)
BIC1006-01Calcimycin A23187
GTR19206340Calcimycin hemicalcium salt
BML-CA100-0010Antibiotic A-23187 (Calcimycin)
GTR19274757-01Calcimycin hemicalcium hemimagnesium
A2297-01Calcimycin discontinued. See A2297
A2297-01Antibiotic A23187 (Calcimycin, Calcium Ionophore A23187)

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