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21-Hydroxyoligomycin A

SKU
H-2481
  • CAS:102042-09-1
  • Formula:C45H74O12
  • MW:807.1 Da
  • Appearance:White Lyophilisate
  • Purity:>95% by HPLC
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Description

21-Hydroxyoligomycin A is a rare member of the oligomycin class isolated as a co-metabolite of nemadectin, hence its original naming as nemadectin omega. 21-Hydroxyoligomycin A is structurally distinct and synthesized by a separate pathway from the nemadectins.

Only limited literature references to this metabolite are available. However, in-house testing suggests that 21-hydroxyoligomycin has a more selective action against mammalian tumor cell lines than oligomycin A, exhibiting only weak antifungal and nematocidal activity.

Isolated from Streptomyces sp.

References

• Structure and Absolute Stereochemistry of 21-Hydroxyoligomycin A. Wagenaar M.M. et al., J Nat Prod. 2007, in
press.
• Plasmid effects on secondary metabolite production by a streptomycete synthesizing an anthelmintic
macrolide.Thomas D.I. et al., J Gen Microbiol. 1991, 137, 2331

Not for human therapeutic use or for medicinal purposes. For research applications only.

More Information
Alternate Name/Synonyms
Nemadectin omega; LL-F28249 omega
SKU
H-2481
CAS #
102042-09-1
Chemical Name
(1S,4E,5'R,6R,6'R,7S,8R,10S,11S,12R,14R,15R,16S,18E,20E,22R,25R,27S,28R,29S)-22-ethyl-7,11,14,15,23-pentahydroxy-6'-[(2S)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethylspiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-oxane]-3,9,13-trione
Chemical Formula
C45H74O12
Molecular Weight
807.1 Da
Appearance
White Lyophilisate
Purity
>95% by HPLC
Solubility
Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility.
Storage Temp
-20°C
THERAPEUTIC AREA
Oncological Disorders
USE
21-hydroxyoligomycin has a more selective action against tumor cells.
MDL NUMBER
MFCD09752734
INCHI
InChI=1S/C45H74O12/c1-12-33-17-15-13-14-16-26(4)42(52)44(11,54)43(53)31(9)40(51)30(8)39(50)29(7)38(49)25(3)18-19-37(48)55-41-28(6)36(23-34(33)47)57-45(32(41)10)21-20-24(2)35(56-45)22-27(5)46/h13-15,17-19,24-36,38,40-42,46-47,49,51-52,54H,12,16,20-23H2,1-11H3/b14-13+,17-15+,19-18+/t24-,25-,26+,27+,28+,29-,30-,31-,32-,33-,34?,35-,36-,38+,40+,41+,42-,44-,45+/m1/s1
SMILES
CC[C@@H]1/C=C/C=C/C[C@@H]([C@H]([C@@](C(=O)[C@@H]([C@H]([C@@H](C(=O)[C@@H]([C@H]([C@@H](/C=C/C(=O)O[C@H]2[C@H]([C@@H](CC1O)O[C@]3([C@@H]2C)CC[C@H]([C@H](O3)C[C@H](C)O)C)C)C)O)C)C)O)C)(C)O)O)C
Handling
Handle in accordance with good industrial hygiene and safety practice.
HandlingHandle in accordance with good industrial hygiene and safety practice.
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