52665-69-7

52665-69-7 structure

Name: Calcimycin
Chemical Name: ionophore A23187
CAS Number: 52665-69-7
Molecular Formula: C₂₉H₃₇N₃O₆
Molecular Weight: 523.621
Catalog: analytical chemistry Analytical reagent Common analytical reagents
Create Date: 2018-03-04 08:00:00
Modify Date: 2026-07-12 10:47:39
Calcimycin (A23187) is an antibiotic and a unique divalent cation ionophore (like calcium and magnesium). It 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 of mammalian cells. It induces apoptosis[1][2][3][4].

Name	ionophore A23187
Synonyms	4-Benzoxazolecboxylicacid,5-(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-dioxaspiroundec-2-yl]methyl] CALCIUMHYPOPHOSPHITE,PURIFIED Bis[5-methylamino-2-[[(6S)-3β,9α,11β-trimethyl-8α-[(S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiroundec-2β-yl]methyl]-4-benzoxazolecboxylic acid]calcium salt CALCIUM HYPOPHOSPHITE TECHNICAL CalciuM Ionophore A23187, froM StrtoMyces chtreusis A23187 (CalciMycin) 5-(methylamino)-2-((3,9,11-trimethyl-8-(1-methyl-4-benzoxazolecboxylicaci Calcium bisphosphinate 11B1 MFCD00151202 CALCIUM PHOSPHINATE 4-BENZOXAZOLECBOXYLIC ACID, 5-(METHYLAMINO)-2-((3,9,11-TRIMETHYL-8-(1-METHYL-2-OXO-2-(1H-PYRROL-2-YL)ETHYL)-1,7-DIOXASPIROUNDEC-2-YL)METHYL)-(6S-(6ALPHA(2S,3S),8BETA(R),9BETA,11ALPHA)) CALCIUM HYPOPHOSPHITE EXTRA PURE,DAC A23187 ANTIBIOTIC A 23187 Phosphinicacid,calciumsalt 5-(Methylamino)-2-[[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiroundec-2-yl]methyl]-4-benzoxazolecboxylic acid Antibiotic A 23187, Calcium Ionophore A23187, Calimycin SBE-β-CD 3s),8-beta(r),9-beta,11-alpha))-lpha(2s 6S-[6a(2S,3S),8b(R),9b,11a]-5-(Methylamino)-2-[[3,9,11-trimethyl-8-[1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-4-benzoxazolecarboxylic Acid 4-Benzoxazolecboxylic acid, 5-(methylamino)-2-[[3,9,11-trimethyl-8-[1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiroundec-2-yl]methyl]-, [6S-[6B1 (2S,3S),8B2 Calimycin Ethacrynic acid-d5 A 23187, CaliMycin CALCIUM IONOPHORE (CALCIMYCIN) FREE ACID III CALCIMYCIN 5-Methylamino-2-[[(2R,3R,6S)-3,9α,11β-trimethyl-8α-[(S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiroundec-2-yl]methyl]-4-benzoxazolecboxylic acid Lime hypophosphite Calcimycin hydrate ANTIBIOTIC A23187 Calcium ionophore A23187 from Strtomyces chtreusis CALCIUM IONOPHORE III CALCIUM IONOPHORE A23187 IONOPHORE A-23187 A23187, Free Acid, Strtomyces chtreusensis A23187, Free Acid, Strtomyces chtreusensis - - Calbiochem Calcium hydrophosphite A23187,free acid 5-(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-dioxaspiroundec-2-yl]methyl]-4-benzoxazolecboxylic acid 2-oxo-2-(1h-pyrrol-2-yl)ethyl)-1,7-dioxaspiroundec-2-yl)methyl),(6s-(6-a CALCIMYCIN A23187 FREE ACID 4-Benzoxazolecboxylic acid, 5-(methylamino)-2-((3,9,11-trimethyl-8-(1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl)-1,7-dioxaspiroundec-2-yl)methyl)-, (6S-(6alpha(2S,3S),8beta(R),9beta,11alpha))-, A23187 (free acid), Calcimycin, Calcium Ionophore A23187 A23187 (Calcimycin), Ca2+ ionophore A23187 MIXED CALCIUM-MAGNESIUM SALT Antibiotic A 23187, Calimycin A23187 FREE ACID Calcimycin [Calcium Ionophore A23187] (R*),9B2 5-(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-DIOXASPIROUNDEC-2-YL]METHYL]-4-BENZOXAZOLECBOXYLIC ACID 5-(Methylamino)-2-({(2S,3S,8S,9R,11R)-3,9,11-trimethyl-8-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)-2-propanyl]-1,7-dioxaspiro[5.5]undec-2-yl}methyl)-1,3-benzoxazole-4-carboxylic acid Calcimycin (Mixed Ca/Mg salt) CALIMYCIN;ANTIBIOTIC A CALCIMYCIN A23187 5-(Methylamino)-2-({(2S,3S,8S,9R,11R)-3,9,11-trimethyl-8-[(2R)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undec-2-yl}methyl)-1,3-benzoxazole-4-carboxylic acid EINECS 258-084-1 Calcimycin, 10 mM in DMSO

Description	Calcimycin (A23187) is an antibiotic and a unique divalent cation ionophore (like calcium and magnesium). It 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 of mammalian cells. It induces apoptosis[1][2][3][4].
Related Catalog	Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Research Areas >> Infection Signaling Pathways >> Autophagy >> Autophagy
References	[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.

Density	1.3±0.1 g/cm3
Boiling Point	710.3±55.0 °C at 760 mmHg
Melting Point	187-190 °C
Molecular Formula	C₂₉H₃₇N₃O₆
Molecular Weight	523.621
Flash Point	383.4±31.5 °C
Exact Mass	523.268250
PSA	126.68000
LogP	5.66
Vapour Pressure	0.0±2.4 mmHg at 25°C
Index of Refraction	1.611
Storage condition	2-8°C

Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xi
Risk Phrases	36/37/38-20/21/22
Safety Phrases	26-36
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	DM4676000
HS Code	29349990

Precursor 7
58288-38-3 78024-03-0 86214-09-7 81550-83-6
100845-53-2 80657-88-1 79558-78-4
DownStream 0

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