Herbimycin

Herbimycin
Names
IUPAC name
[(2R,3S,5S,6R,7S,8E,10R,11S,12E,14E)-2,5,6,11-tetramethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-8,12,14,18,21-pentaen-10-yl] carbamate
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C30H42N2O9/c1-16-10-9-11-23(37-5)28(41-30(31)36)18(3)12-17(2)27(40-8)24(38-6)13-19(4)26(39-7)21-14-20(33)15-22(25(21)34)32-29(16)35/h9-12,14-15,17,19,23-24,26-28H,13H2,1-8H3,(H2,31,36)(H,32,35)/b11-9-,16-10+,18-12+/t17-,19-,23-,24-,26+,27+,28-/m0/s1 checkY
    Key: MCAHMSDENAOJFZ-BVXDHVRPSA-N checkY
  • InChI=1S/C30H42N2O9/c1-16-10-9-11-23(37-5)28(41-30(31)36)18(3)12-17(2)27(40-8)24(38-6)13-19(4)26(39-7)21-14-20(33)15-22(25(21)34)32-29(16)35/h9-12,14-15,17,19,23-24,26-28H,13H2,1-8H3,(H2,31,36)(H,32,35)/b11-9-,16-10+,18-12+/t17-,19-,23-,24-,26+,27+,28-/m0/s1
    Key: MCAHMSDENAOJFZ-BVXDHVRPBC
  • Key: MCAHMSDENAOJFZ-BVXDHVRPSA-N
SMILES
  • NC(=O)O[C@H]1C(/C)=C/[C@H](C)[C@@H](OC)[C@@H](OC)C[C@H](C)[C@@H](OC)C\2=C\C(=O)\C=C(\NC(=O)C(\C)=C\C=C/[C@@H]1OC)C/2=O
Properties
Chemical formula
 C30H42N2O9
Molar mass 574.671 g·mol−1
Solubility hygroscopic
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Herbimycin is a benzoquinone ansamycin antibiotic that binds to Hsp90 (Heat Shock Protein 90) and alters its function. Hsp90 client proteins play important roles in the regulation of the cell cycle, cell growth, cell survival, apoptosis, angiogenesis and oncogenesis.

It was originally found by its herbicidal activity, and thus named. The most recent herbimycins to be discovered, herbimycins D-F, were isolated from a Streptomyces isolated from thermal vents associated with the Ruth Mullins coal fire in Appalachian Kentucky.[1]

Synonyms

  • Antibiotic Tan 420F
  • Herbimycin A

Biological activity

Herbimycin induces the degradation of proteins that are need to be mutated in tumor cells such as v-Src, Bcr-Abl and p53 preferentially over their normal cellular counterparts. This effect is mediated via Hsp90.

See also

  • Geldanamycin
  • Satoshi Ōmura

References

  1. ↑ Shaaban, KA; Wang, X; Elshahawi, SI; Ponomareva, LV; Sunkara, M; Copley, GC; Hower, JC; Morris, AJ; Kharel, MK; Thorson, JS (27 September 2013). "Herbimycins D-F, ansamycin analogues from Streptomyces sp. RM-7-15". Journal of Natural Products. 76 (9): 1619–26. doi:10.1021/np400308w. PMC 3852429. PMID 23947794.
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