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perimycin A
Sign in to savePerimycin, also known as aminomycin and fungimycin, is polyene antibiotic produced by Streptomyces coelicolor var. aminophilus. The compound exhibits antifungal properties. __TOC__ == Composition == Perimycin is produced naturally as a mixture of three types: A, B and C, with type A being the major component. All types consist of a polyketide core with a perosamine sugar moiety. The variations occur at the end of the core opposite the perosamine moiety. Perimycin A has an aromatic group in this position, whereas the identities of the analogous groups in the other perimycin types are currently
In the Vinony graph
Within Vinony's link graph, perimycin A is referenced by 5 other articles, and connects out to digital object identifier, pharmacology and chemical formula.
It sits within the topics Antifungals, Chembox image size set and Macrolide antibiotics.
Its subject is documented across 6 Wikipedia language editions.
Chemical data
- Formula
- C59H88N2O17
- Molecular weight
- 1097.3 g/mol
- IUPAC name
- (1R,3S,5S,7R,9R,13R,17R,18S,19E,21E,23Z,25Z,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,7,9,13,37-heptahydroxy-17-[(2S)-5-hydroxy-7-[4-(methylamino)phenyl]-7-oxoheptan-2-yl]-18,36-dimethyl-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-11,15-dione
- SMILES
- C[C@H]1/C=C/C=C/C=C\C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@H](C[C@H](C[C@H](CC(=O)C[C@H](CC(=O)O[C@@H]1[C@@H](C)CCC(CC(=O)C3=CC=C(C=C3)NC)O)O)O)O)O)O)O)O)C)O[C@H]4[C@H]([C@H]([C@@H]([C@H](O4)C)N)O)O
- InChIKey
- SIJFZOSSGXKJCI-FTNWOYNKSA-N
- XLogP
- 4
- Polar surface area
- 328 Ų
- H-bond donors
- 12
- H-bond acceptors
- 19
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 1096.608
Show 3 more facts
- chemical formula
- C₅₉H₈₈N₂O₁₇
- canonical SMILES
- CC1C=CC=CC=CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC(CC(CC(CC(=O)CC(CC(=O)OC1C(C)CCC(CC(=O)C3=CC=C(C=C3)NC)O)O)O)O)O)O)O)O)C)OC4C(C(C(C(O4)C)N)O)O
- isomeric SMILES
- C[C@H]1/C=C/C=C/C=C\C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@H](C[C@H](C[C@H](CC(=O)C[C@H](CC(=O)O[C@@H]1[C@@H](C)CCC(CC(=O)C3=CC=C(C=C3)NC)O)O)O)O)O)O)O)O)C)O[C@H]4[C@H]([C@H]([C@@H]([C@H](O4)C)N)O)O
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Composition
- Usage
- References
Perimycin, also known as aminomycin and fungimycin, is polyene antibiotic produced by Streptomyces coelicolor var. aminophilus. The compound exhibits antifungal properties. __TOC__ == Composition == Perimycin is produced naturally as a mixture of three types: A, B and C, with type A being the major component. All types consist of a polyketide core with a perosamine sugar moiety. The variations occur at the end of the core opposite the perosamine moiety. Perimycin A has an aromatic group in this position, whereas the identities of the analogous groups in the other perimycin types are currently undetermined.
== Usage == Polyene antibiotics in general are often toxic to humans and have poor bioavailability. Thus, with the notable exception of amphotericin B, they are often not used clinically. Perimycin has been shown to be an effective antifungal compound, but is not widely used in clinical settings.
Excerpted from Wikipedia’s “perimycin A” article, available under the CC BY-SA 4.0 licence.