Structure via PubChem · Public domain (PubChem)
calcimycin A23187
Sign in to saveAlso known as 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, calcium ionophore A23187
A23187 is a mobile ion-carrier that forms stable complexes with divalent cations (ions with a charge of +2). A23187 is also known as Calcimycin, Calcium Ionophore, Antibiotic A23187 and Calcium Ionophore A23187. It is produced at fermentation of Streptomyces chartreusensis.
Chemical data
- Formula
- C29H37N3O6
- Molecular weight
- 523.6 g/mol
- IUPAC name
- 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
- 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
- InChIKey
- HIYAVKIYRIFSCZ-CYEMHPAKSA-N
- XLogP
- 5.9
- Polar surface area
- 127 Ų
- H-bond donors
- 3
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- male infertility, infertility
via ChEMBL · EBI
Research
12,056 papers- Calcimycin mediates apoptosis in breast and cervical cancer cell lines by inducing intracellular calcium levels in a P2RX4-dependent manner.Biochimica et biophysica acta. General subjects · 2024
- Semi-synthesis of A23187 (calcimycin) analogs. III. Modification of benzoxazole ring substituents, ionophorous properties in an organic phase.The Journal of antibiotics · 1986
- Kinetic properties of cation/H(+)-exchange: calcimycin (A23187)-mediated Ca2+/2H(+)-exchange on the bilayer lipid membrane.Biochimica et biophysica acta · 1990
- Semi-synthesis of A23187 (calcimycin) analogs. IV. Cation carrier properties in mitochondria of analogs with modified benzoxazole rings. Antimicrobial activity.The Journal of antibiotics · 1986
- Semisynthesis of A23187 (calcimycin) analogs. II. Introduction of a methyl group on the benzoxazole ring.The Journal of antibiotics · 1984
via PubMed
Wikidata facts
- Mass
- 523.268
Show 5 more facts
- chemical formula
- C₂₉H₃₇N₃O₆
- isomeric 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
- canonical SMILES
- CC1CCC2(C(CC(C(O2)C(C)C(=O)C3=CC=CN3)C)C)OC1CC4=NC5=C(O4)C=CC(=C5C(=O)O)NC
- found in taxon
- Streptomyces
- Commons category
- A23187
via Wikidata · CC0
~4 min read
Encyclopedic overview
5 sectionsContents
- Actions and uses
- Biosynthesis
- Commercial availability
- References
- External links
{{Drugbox |Verifiedfields = changed |Watchedfields = changed |verifiedrevid = 461749035 |IUPAC_name = 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-dioxaspiro[5.5]undec-2-yl}methyl)-1,3-benzoxazole-4-carboxylic acid |image = A23187.png |image_class = skin-invert-image
|tradename =
Excerpted from Wikipedia’s “calcimycin A23187” article, available under the CC BY-SA 4.0 licence.