Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H44O6 |
| Molecular Weight | 464.6347 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]([C@H](O)CCC(C)(C)O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C
InChI
InChIKey=UPEZCKBFRMILAV-JMZLNJERSA-N
InChI=1S/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22+,23-,25+,26+,27+/m0/s1
| Molecular Formula | C27H44O6 |
| Molecular Weight | 464.6347 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Ecdysone is the steroidal prohormone of the major insect moulting hormone 20-hydroxyecdysone. It groups with its homologues the steroidal molting hormones in arthropods, but they also occur in other phyla (Invertebrates and Tunicates) where they can play different roles. Ecdysone receptor (EcR), functions as a receptor for the ecdysteroid molting hormones of insects. Since ecdysone administration has no apparent effect on mammals, its use for regulating genes should be excellent for transient inducible expression of any gene in transgenic mice and for gene therapy.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| The expression of the let-7 small regulatory RNA is controlled by ecdysone during metamorphosis in Drosophila melanogaster. | 2002-04-01 |
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| Cyclic dibenzoylhydrazines reproducing the conformation of ecdysone agonists, RH-5849. | 2002-04 |
|
| Ecdysone-inducible expression of oncogenic Ha-Ras in NIH 3T3 cells leads to transient nuclear localization of activated extracellular signal-regulated kinase regulated by mitogen-activated protein kinase phosphatase-1. | 2002-03-01 |
|
| Cellular immune response to parasite infection in the Drosophila lymph gland is developmentally regulated. | 2002-03-01 |
|
| reaper is required for neuroblast apoptosis during Drosophila development. | 2002-03 |
|
| Neurotoxic mechanisms by Alzheimer's disease-linked N141I mutant presenilin 2. | 2002-03 |
|
| Environmental antiecdysteroids alter embryo development in the crustacean Daphnia magna. | 2002-02-15 |
|
| Limnantheoside C (20-hydroxyecdysone 3-O-beta-D-glucopyranosyl-[1-->3]-beta-D-xylopyranoside), a phytoecdysteroid from seeds of Limnanthes alba (limnanthaceae). | 2002-02-12 |
|
| Inducible expression of a constitutively active mutant of mitogen-activated protein kinase kinase 7 specifically activates c-JUN NH2-terminal protein kinase, alters expression of at least nine genes, and inhibits cell proliferation. | 2002-02-01 |
|
| Dirofilaria immitis encodes Di-nhr-7, a putative orthologue of the Drosophila ecdysone-regulated E78 gene. | 2002-02 |
|
| Analyzing the repressive function of ultraspiracle, the Drosophila RXR, in Drosophila eye development. | 2002-02 |
|
| Microencapsulated iNOS-expressing cells cause tumor suppression in mice. | 2002-02 |
|
| Photochemical transformation of 20-hydroxyecdysone: production of monomeric and dimeric ecdysteroid analogues. | 2002-02 |
|
| Effect of RH-5992 on adult development in the spruce budworm, Choristoneura fumiferana. | 2002-02 |
|
| Comparative toxicity and ecdysone receptor affinity of non-steroidal ecdysone agonists and 20-hydroxyecdysone in Chironomus tentans. | 2002-02 |
|
| Inhibition of [3H]ponasterone A binding by ecdysone agonists in the intact Kc cell line. | 2002-02 |
|
| Phytoecdysteroids from the juice of Serratula coronata L. (Asteraceae). | 2002-02 |
|
| Stage-specific expression of the chitin synthase DmeChSA and DmeChSB genes during the onset of Drosophila metamorphosis. | 2002-02 |
|
| Isolation and characterization of novel mutations of the Broad-Complex, a key regulatory gene of ecdysone induction in Drosophila melanogaster. | 2002-02 |
|
| Ecdysone-regulated puff genes 2000. | 2002-02 |
|
| Proceedings from the Fourteenth Ecdysone Workshop. Rapperwil, Switzerland, 24-27 July 2000. | 2002-02 |
|
| Characterization and spatiotemporal expression of orchestin, a gene encoding an ecdysone-inducible protein from a crustacean organic matrix. | 2002-01-15 |
|
| Cloning and functional analysis of pyruvate kinase promoter region from Drosophila melanogaster. | 2002-01 |
|
| The induction of DNA puff BhC4-1 gene is a late response to the increase in 20-hydroxyecdysone titers in last instar dipteran larvae. | 2002-01 |
|
| Control and biochemical nature of the ecdysteroidogenic pathway. | 2002 |
|
| Endocrine insights into the evolution of metamorphosis in insects. | 2002 |
|
| Identification and quantitative analysis of the phytoecdysteroids in Silene species (Caryophyllaceae) by high-performance liquid chromatography. Novel ecdysteroids from S. pseudotites. | 2001-11-23 |
|
| Selective binding of Drosophila BR-C isoforms to a distal regulatory element in the hsp23 promoter. | 2001-11-01 |
|
| A microsomal ecdysone-binding cytochrome P450 from the insect Locusta migratoria purified by sequential use of type-II and type-I ligands. | 2001-11 |
|
| Ecdysone-inducible foreign gene expression in stably-transformed lepidopteran insect cells. | 2001-10 |
|
| Molecular mechanisms of developmental timing in C. elegans and Drosophila. | 2001-10 |
|
| Mode of action of the ecdysone agonist tebufenozide (RH-5992), and an exclusion mechanism to explain resistance to it. | 2001-10 |
|
| Ecdysone-regulated chromosome puffing in the salivary glands of the Mediterranean fruit fly, Ceratitis capitata. | 2001-10 |
|
| Conditional transgenic technologies. | 2001-10 |
|
| Requirement of co-factors for the ligand-mediated activity of the insect ecdysteroid receptor in yeast. | 2001-10 |
|
| Overexpression of candidate tumor suppressor gene FUS1 isolated from the 3p21.3 homozygous deletion region leads to G1 arrest and growth inhibition of lung cancer cells. | 2001-09-27 |
|
| Protection against chemotherapy-induced cytotoxicity by cyclin-dependent kinase inhibitors (CKI) in CKI-responsive cells compared with CKI-unresponsive cells. | 2001-09-27 |
|
| Human cell lines expressing hormone regulated T7 RNA polymerase localized at distinct intranuclear sites. | 2001-09-05 |
|
| Antisense expression of the 20-hydroxyecdysone receptor (EcR) in transfected mosquito cells uncovers a new EcR isoform that varies at the C-terminal end. | 2001-09 |
|
| Evaluation of the tetracycline- and ecdysone-inducible systems for expression of neurotransmitter receptors in mammalian cells. | 2001-09 |
|
| Bicistronic expression of ecdysone-inducible receptors in mammalian cells. | 2001-09 |
|
| Neonicotinoid insecticides alter diapause behavior and survival of overwintering white grubs (Coleoptera: Scarabaeidae). | 2001-09 |
|
| Transcriptional regulation of the mosquito vitellogenin gene via a blood meal-triggered cascade. | 2001-08-22 |
|
| A novel inducible expression system to study transdominant mutants of HIV-1 Vpr. | 2001-08-15 |
|
| Method for screening ecdysone-inducible stable cell lines. | 2001-08 |
|
| CHMP1 is a novel nuclear matrix protein affecting chromatin structure and cell-cycle progression. | 2001-07 |
|
| Regulated gene expression in glioma cells: a comparison of three inducible systems. | 2001-05 |
|
| Manipulation of gene expression by an ecdysone-inducible gene switch in tumor xenografts. | 2001 |
|
| Titrating the expression of a Gi protein-coupled receptor using an ecdysone-inducible system in CHO-K1 cells. | 2001 |
|
| Effects of the ecdysoneless mutant on synaptic efficacy and structure at the neuromuscular junction in Drosophila larvae during normal and prolonged development. | 2001 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 23:05:07 GMT 2025
by
admin
on
Mon Mar 31 23:05:07 GMT 2025
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| Record UNII |
RH692X7B7B
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| Record Status |
Validated (UNII)
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| Record Version |
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19212
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m4808
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RH692X7B7B
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16688
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Ecdysone
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DTXSID2020553
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222-760-4
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3604-87-3
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