Maximiscin (original) (raw)

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Maximiscin
Names
Preferred IUPAC name Methyl (3_R_,4_R_,5_R_,6_R_)-6-({3-[(1_R_,2_S_,4_R_,6_S_)-2-ethenyl-4,6-dimethylcyclohexyl]-4-hydroxy-2-oxopyridin-1(2_H_)-yl}oxy)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylate
Identifiers
CAS Number 1612154-44-5
3D model (JSmol) Interactive image
ChEMBL ChEMBL3903473
ChemSpider 34485502
PubChem CID 132521702
InChI 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/s1Key: BHUFOFQGYXAGAC-XMGLCDBZSA-N
SMILES 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
Chemical formula 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

Chemical compound

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]

  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.