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;
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	574.66 g/mol
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]

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.

References

^ 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.

External links

Herbimycin A from Center for Pharmaceutical Research and Innovation

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[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]

Synonyms

Biological activity

See also

References

External links