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macbecin I
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Macbecins are a pair of chemical compounds in the ansamycin family of antibiotics. They are designated macbecin I and macbecin II and they were first isolated from actinomycete bacteria. Macbecin possesses antitumor properties. In vitro studies have shown that macbecins are effective in the eradication of Gram-positive bacteria, fungi, and protozoa including Tetrahymena pyriformis. ==Structure== Macbecins have an unusual macrocyclic lactam structure. The two variants, macbecin I and II, correspond to the oxidized 1,4-benzoquinone and reduced hydroquinone, respectively.
Chemical data
- Formula
- C30H42N2O8
- Molecular weight
- 558.7 g/mol
- IUPAC name
- [(4E,6Z,8S,10E,12R,13S,14R,16S,17R)-13,14,17-trimethoxy-4,8,10,12,16-pentamethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate
- SMILES
- C[C@H]1C[C@H]([C@H]([C@@H](/C=C(/C([C@H](/C=C\C=C(\C(=O)NC2=CC(=O)C=C([C@@H]1OC)C2=O)/C)C)OC(=O)N)\C)C)OC)OC
- InChIKey
- PLTGBUPHJAKFMA-OEPVMNMSSA-N
- XLogP
- 2.7
- Polar surface area
- 143 Ų
- H-bond donors
- 2
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 558.294116
Show 3 more facts
- isomeric SMILES
- C[C@H]1C[C@H]([C@H]([C@@H](/C=C(/C([C@H](/C=C\C=C(\C(=O)NC2=CC(=O)C=C([C@@H]1OC)C2=O)/C)C)OC(=O)N)\C)C)OC)OC
- chemical formula
- C₃₀H₄₂N₂O₈
- canonical SMILES
- CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C=C(C1OC)C2=O)C)C)OC(=O)N)C)C)OC)OC
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Structure
- Mechanism of action
- References
- External links
Macbecins are a pair of chemical compounds in the ansamycin family of antibiotics. They are designated macbecin I and macbecin II and they were first isolated from actinomycete bacteria. Macbecin possesses antitumor properties. In vitro studies have shown that macbecins are effective in the eradication of Gram-positive bacteria, fungi, and protozoa including Tetrahymena pyriformis. ==Structure== Macbecins have an unusual macrocyclic lactam structure. The two variants, macbecin I and II, correspond to the oxidized 1,4-benzoquinone and reduced hydroquinone, respectively.
==Mechanism of action== Macbecins mechanism of action is in part due to heat shock protein Hsp90 protein inhibition.
Excerpted from Wikipedia’s “macbecin I” article, available under the CC BY-SA 4.0 licence.