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Structure Database (LMSD)

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Common Name

20-hydroxyecdysone

Systematic Name

2β,3β,14α,20,22R,25-hexahydroxy-5β-cholest-7-en-6-one

Synonyms

20-Hydroxyecdysone
20-OH ecdysone

LM ID

LMST01010209

Formula

C₂₇H₄₄O₇

Exact Mass

Calculate m/z

480.308705

Sum Composition

ST 27:2;O7

Status

Curated

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Classification

Biological Context

20-hydroxy Ecdysone is an ecdysteroid hormone produced in arthropod species that induces developmental changes associated with ecdysis and the completion of metamorphosis.¹ It is also produced in plants as a defensive strategy to disrupt the development of insect pests.² In target tissues, 20-hydroxy ecdysone binds to the nuclear hormone receptor, ecdysone receptor, initiating a signaling cascade that results in cell cycle arrest.^1,3 Ecdysteroids such as this compound have been employed as tools in inducible gene regulation systems controlled by reporter cells transfected with the ecdysone receptor.^4,5

This information has been provided by Cayman Chemical

References

1. Saez, E., Nelson, M.C., Eshelman, B., et al. Identification of ligands and coligands for the ecdysone-regulated gene switch. Proc. Natl. Acad. Sci. USA 97(26), 14512-14517 (2000).

2. Karzenowski, D., Potter, D.W., and Padidam, M. Inducible control of transgene expression with ecdysone receptor: Gene switches with high sensitivity, robust expression, and reduced size. Biotechniques 39(2), 191-192 (2005).

3. Fallon, A.M., and Gerenday, A. Ecdysone and the cell cycle: Investigations in a mosquito cell line. J. Insect Physiol. 56(10), 1396-1401 (2010).

4. Cai, M.J., Dong, D.J., Wang, Y., et al. G-protein-coupled receptor participates in 20-hydroxyecdysone signaling on the plasma membrane. Cell Commun. Signal. 12, 11-16 (2014).

5. Boo, K.H., Lee, D., Jeon, G.L., et al. Distribution and biosynthesis of 20-hydroxyecdysone in plants of Achyranthes japonica Nakai. Biosci. Biotechnol. Biochem. 74(11), 2226-2231 (2010).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Bombyx mori (#7091)

Insecta (#50557)

20-hydroxy-ecdyson, isoliert aus insekten,
Tetrahedron Letts, 1966

DOI: 10.1016/S0040-4039(01)99901-0

String Representations

InChiKey (Click to copy)

NKDFYOWSKOHCCO-YPVLXUMRSA-N

InChi (Click to copy)

InChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1

SMILES (Click to copy)

C1[C@H](O)[C@H](O)C[C@@]2([H])C(=O)C=C3[C@@](CC[C@]4([C@@]3(O)CC[C@]4([H])[C@](O)(C)[C@H](O)CCC(O)(C)C)C)([H])[C@]21C