Herbimycin

Herbimycin

Names
IUPAC names [(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 Registry Number	70563-58-5 Y
ChEMBL	ChEMBL1159659 N
ChemSpider	10272738 Y
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 Y Key: MCAHMSDENAOJFZ-BVXDHVRPSA-N Y 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
Jmol-3D images	Image
PubChem	6436247
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	574.66 g/mol
Solubility	hygroscopic
Hazards
Main hazards	toxic
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/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.

Synonyms

• Antibiotic Tan 420F
• Herbimycin A

Biological activity

Herbimycin induces the degradation of proteins that are 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