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.
In the Vinony graph
Within Vinony's link graph, calcimycin A23187 is referenced by 13 other articles, and connects out to ionophore, fungi and cancer.
Vinony files it under Antibiotics, Benzoxazoles and Chemical pages without DrugBank identifier.
Its subject is documented across 7 Wikipedia language editions.
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.