Maximiscin

Maximiscin is a polyketide-shikimate chemical compound isolated from Tolypocladium that shows tumor growth suppression in an animal model.[1] The discovery of maximiscin was the result of a citizen scientist crowdsourcing project by the University of Oklahoma.[2] The soil sample which yielded maximiscin was sent by a woman from Salcha, Alaska.[3]

Maximiscin
Names
Preferred IUPAC name
Methyl (3R,4R,5R,6R)-6-({3-[(1R,2S,4R,6S)-2-ethenyl-4,6-dimethylcyclohexyl]-4-hydroxy-2-oxopyridin-1(2H)-yl}oxy)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C23H31NO8/c1-5-13-9-11(2)8-12(3)17(13)18-15(25)6-7-24(22(18)29)32-21-14(23(30)31-4)10-16(26)19(27)20(21)28/h5-7,10-13,16-17,19-21,25-28H,1,8-9H2,2-4H3/t11-,12+,13-,16+,17-,19+,20+,21-/m1/s1
    Key: BHUFOFQGYXAGAC-XMGLCDBZSA-N
  • COC(=O)C1=C[C@H](O)[C@H](O)[C@H](O)[C@@H]1ON1C=CC(O)=C([C@@H]2[C@@H](C)C[C@@H](C)C[C@H]2C=C)C1=O
Properties
C23H31NO8
Molar mass 449.500 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Du, L; Robles, AJ; King, JB; Powell, DR; Miller, AN; Mooberry, SL; Cichewicz, RH (2013). "Maximiscin, a Novel Shikimate-Polyketide-NRPS Hybrid Metabolite Obtained from Tolypocladium Sp. With Potent Antitumor Activities". Planta Medica. 79 (10). doi:10.1055/s-0033-1348528.
  2. Du, L; Robles, AJ; King, JB; Powell, DR; Miller, AN; Mooberry, SL; Cichewicz, RH (2013). "Crowdsourcing Natural Products Discovery to Access Uncharted Dimensions of Fungal Metabolite Diversity". Angewandte Chemie International Edition in English. 53 (3): 804–9. doi:10.1002/anie.201306549. PMC 4028707. PMID 24285637.
  3. Julianne Wyrick (December 5, 2013). "Crowdsourcing unearths promising anticancer compound". chemistryworld.com. Royal Society of Chemistry.


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