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	70563-58-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1159659 ;
ChemSpider	10272738 ;
PubChem CID	6436247;
UNII	815WDV2HST ;
CompTox Dashboard (EPA)	DTXSID4042674 ;
	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 Key: MCAHMSDENAOJFZ-BVXDHVRPSA-N ; 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). verify (what is ?) 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]

^ 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.

[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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