Lucibufagin

Lucibufagin
Identifiers
3D model (JSmol)	C: Interactive image;
ChEBI	C: CHEBI:134224;
ChEMBL	C: ChEMBL485697;
ChemSpider	C: 24702088;
PubChem CID	C: 15924888;
	InChI C: InChI=1S/C28H36O10/c1-14(29)37-19-11-25(3)22-18(7-9-27(25,34)12-20(19)38-15(2)30)28(35)10-8-17(16-5-6-21(31)36-13-16)26(28,4)24(33)23(22)32/h5-6,13,17-20,22-23,32,34-35H,7-12H2,1-4H3/t17-,18-,19+,20-,22-,23+,25-,26+,27+,28+/m1/s1 Key: DVEVNJSTCHVUOO-AXGBFFCYSA-N;
	SMILES C: C=1(C=CC(OC1)=O)[C@@H]2[C@]3(C([C@H]([C@@]4([C@]5(C[C@@H]([C@@H](C[C@]5(CC[C@]4([C@]3(CC2)O)[H])O)OC(=O)C)OC(=O)C)C)[H])O)=O)C;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

A lucibufagin is a defensive steroid produced by several species of firefly to make them unpalatable to predators such as spiders and birds.^[1] Certain species of firefly that do not themselves produce lucibufagins have been observed to eat other species of firefly that do produce the steroid to gain the defensive properties for themselves.^[2] The lucibufagins are a set of three related compounds (Lucibufagin A, B, and C), and are in the same structural class as the bufadienolides.^[3]

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References

^ P.J. Leisch (Summer 2018). "Five things everyone should know about... Fireflies". Grow. 11 (3): 5.
^ Segelken, Roger. "Lured and liquidated, gullible male fireflies supply 'femmes fatales' with a lifesaving chemical | Cornell Chronicle". news.cornell.edu. Retrieved 5 July 2018.
^ Eisner, Thomas; Wiemer, David F.; Haynes, LeRoy W.; Meinwald, Jerrold (1978). "Lucibufagins: Defensive steroids from the fireflies Photinus ignitus and P. marginellus (Coleoptera: Lampyridae)". Proc Natl Acad Sci. 75 (2): 905–908. Bibcode:1978PNAS...75..905E. doi:10.1073/pnas.75.2.905. PMC 411366. PMID 16592501.

[1] P.J. Leisch (Summer 2018). "Five things everyone should know about... Fireflies". Grow. 11 (3): 5.

[2] Segelken, Roger. "Lured and liquidated, gullible male fireflies supply 'femmes fatales' with a lifesaving chemical | Cornell Chronicle". news.cornell.edu. Retrieved 5 July 2018.

[3] Eisner, Thomas; Wiemer, David F.; Haynes, LeRoy W.; Meinwald, Jerrold (1978). "Lucibufagins: Defensive steroids from the fireflies Photinus ignitus and P. marginellus (Coleoptera: Lampyridae)". Proc Natl Acad Sci. 75 (2): 905–908. Bibcode:1978PNAS...75..905E. doi:10.1073/pnas.75.2.905. PMC 411366. PMID 16592501.

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Identifiers

3D model (JSmol)	C: Interactive image
ChEBI	C: CHEBI:134224
ChEMBL	C: ChEMBL485697
ChemSpider	C: 24702088
PubChem CID	C: 15924888
InChI C: InChI=1S/C28H36O10/c1-14(29)37-19-11-25(3)22-18(7-9-27(25,34)12-20(19)38-15(2)30)28(35)10-8-17(16-5-6-21(31)36-13-16)26(28,4)24(33)23(22)32/h5-6,13,17-20,22-23,32,34-35H,7-12H2,1-4H3/t17-,18-,19+,20-,22-,23+,25-,26+,27+,28+/m1/s1 Key: DVEVNJSTCHVUOO-AXGBFFCYSA-N
SMILES C: C=1(C=CC(OC1)=O)[C@@H]2[C@]3(C([C@H]([C@@]4([C@]5(C[C@@H]([C@@H](C[C@]5(CC[C@]4([C@]3(CC2)O)[H])O)OC(=O)C)OC(=O)C)C)[H])O)=O)C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references