Macbecin

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.^[1][2] Macbecin possesses antitumor properties.^[1] In vitro studies have shown that macbecins are effective in the eradication of Gram-positive bacteria, fungi, and protozoa including Tetrahymena pyriformis.^[1]

Macbecins

Macbecin I
Macbecin II
Names
IUPAC names I: (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 II: (4E,6Z,8S,10E,12R,13S,14R,16S,17R)-20,22-dihydroxy-13,14,17-trimethoxy-4,8,10,12,16-pentamethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(22),4,6,10,18,20-hexaen-9-yl carbamate
Identifiers
CAS Number	I: 73341-72-7 Y II: 73341-73-8
3D model (JSmol)	I: Interactive image II: Interactive image
ChemSpider	I: 65321675 II: 129561980
PubChem CID	I: 5458728 II: 5458729
SMILES I: 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 II: C[C@H]1C[C@H]([C@H]([C@@H](/C=C(/C([C@H](/C=C\C=C(\C(=O)NC2=CC(=CC(=C2O)[C@@H]1OC)O)/C)C)OC(=O)N)\C)C)OC)OC
Properties
Chemical formula	I: C30H42N2O8 II: C30H44N2O8
Molar mass	I: 558.66 g/mol II: 560.68 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

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.^[2]

Mechanism of action

Macbecins mechanism of action is in part due to heat shock protein Hsp90 protein inhibition.^[3]