Ecdysone

Ecdysone: Ecdysone

IUPAC name

(2S,3R,5R,9R,10R,13R,14S,17R)-17- [(2S,3R)-3,6-dihydroxy-6-methylheptan- 2-yl]-2,3,14-trihydroxy-10,13-dimethyl- 2,3,4,5,9,11,12,15,16,17-decahydro- 1H-cyclopenta[a]phenanthren-6-one

Identifiers

CAS number 3604-87-3^Y

PubChem 19212

ChemSpider 18130^Y

ChEBI CHEBI:16688^Y

ChEMBL CHEMBL549300^Y

Jmol-3D images Image 1

SMILES

O=C1\C=C3/[C@@H]([C@]2(C[C@H](O)[C@H](O)C[C@@H]12)C)CC[C@]4([C@@]3(O)CC[C@@H]4[C@H](C)[C@H](O)CCC(O)(C)C)C

InChI

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^Y
Key: UPEZCKBFRMILAV-JMZLNJERSA-N^Y
InChI=1/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
Key: UPEZCKBFRMILAV-JMZLNJERBR

Properties

Molecular formula C₂₇H₄₄O₆

Molar mass 464.63 g/mol

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Ecdysone is a steroidal prohormone of the major insect molting hormone 20-hydroxyecdysone, which is secreted from the prothoracic glands. Insect molting hormones (ecdysone and its homologues) are generally called ecdysteroids. Ecdysteroids act as moulting hormones of arthropods but also occur in other related phyla where they can play different roles. In Drosophila melanogaster, an increase in ecdysone concentration induces the expression of genes coding for proteins that the larva requires, and it causes chromosome puffs (sites of high expression) to form. Ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects. These phytoecdysteroids have been reputed to have medicinal value and are part of herbal adaptogenic remedies like Cordyceps, yet an ecdyseroid precursor in plants has been shown to have cytotoxic properties ^[1]. A pesticide sold with the name MIMIC has ecdysteroid activity, although its chemical structure has little resemblance to the ecdysteroids.

See also

Ecdysone receptor

External links

Ecdybase, The Ecdysone Handbook - a free online ecdysteroids database

Notes

^ Wang YS, Yang JH, Luo SD, Zhang HB, Li L, Molecules. 2007;12(3):536-42

Categories:
Entomology
Steroids
Insect stubs

Ecdysone

IUPAC name (2S,3R,5R,9R,10R,13R,14S,17R)-17- [(2S,3R)-3,6-dihydroxy-6-methylheptan- 2-yl]-2,3,14-trihydroxy-10,13-dimethyl- 2,3,4,5,9,11,12,15,16,17-decahydro- 1H-cyclopenta[a]phenanthren-6-one
Identifiers
CAS number	3604-87-3^Y
PubChem	19212
ChemSpider	18130^Y
ChEBI	CHEBI:16688^Y
ChEMBL	CHEMBL549300^Y
Jmol-3D images	Image 1
SMILES O=C1\C=C3/[C@@H]([C@]2(C[C@H](O)[C@H](O)C[C@@H]12)C)CC[C@]4([C@@]3(O)CC[C@@H]4[C@H](C)[C@H](O)CCC(O)(C)C)C
InChI 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^Y Key: UPEZCKBFRMILAV-JMZLNJERSA-N^Y InChI=1/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 Key: UPEZCKBFRMILAV-JMZLNJERBR
Properties
Molecular formula	C₂₇H₄₄O₆
Molar mass	464.63 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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ecdysone — [ ɛkdizɔn; ɛkdizon ] n. f. • 1955; all. Ecdyson, de Ecdysis « mue », gr. ekdusis « action de se dépouiller » ♦ Biol. Hormone produite par les glandes du prothorax des insectes, qui stimule la mue des larves. ● ecdysone nom féminin (grec ekdusis,… … Encyclopédie Universelle
Ecdysone — [griechisch], Singular Ecdyson das, s, Ekdysone, Steroidhormone, die bei Insekten und Krebsen die Häutungen der verschiedenen Entwicklungsstadien steuern. Das Ecdyson (α Ecdyson) wird bei Insekten in der … Universal-Lexikon
ecdysone — [ek′də sōn΄] n. [ ECDYSIS + ONE] a hormone produced in the prothoracic glands of insects or in similar glands in crustaceans, for stimulating growth and the molting of the exoskeleton … English World dictionary
Ecdysone — Formules de l ecdysone et de la 20 hydroxy ecdysone (en rouge, l hydroxyle supplémentaire sur le carbone 20) L ecdysone est une hormone stéroïde intervenant notamment dans le processus de la mue des arthropodes et dans le contrôle de leur… … Wikipédia en Français
ecdysone — Family of steroid hormones found in insects, crustaceans and plants. In insects, a ecdysone stimulates moulting. The steadily maturing character of the moults is affected by steadily decreasing levels of juvenile hormone. b ecdysone (ecdysterone) … Dictionary of molecular biology
Ecdysone receptor — protein Name = Ecdysone receptor protein, Drosophila melanogaster caption = width = HGNCid = Symbol = EcR AltSymbols = EcRH, NR1H1 EntrezGene = 35540 OMIM = RefSeq = UniProt = P34021 PDB = 1R0O ECnumber = Chromosome = Arm = Band =… … Wikipedia
Ecdysone O-acyltransferase — In enzymology, an ecdysone O acyltransferase (EC number|2.3.1.139) is an enzyme that catalyzes the chemical reaction:palmitoyl CoA + ecdysone ightleftharpoons CoA + ecdysone palmitateThus, the two substrates of this enzyme are palmitoyl CoA and… … Wikipedia
Ecdysone 20-monooxygenase — In enzymology, an ecdysone 20 monooxygenase (EC number|1.14.99.22) is an enzyme that catalyzes the chemical reaction:ecdysone + AH2 + O2 ightleftharpoons 20 hydroxyecdysone + A + H2OThe 3 substrates of this enzyme are ecdysone, AH2, and O2,… … Wikipedia
Ecdysone oxidase — In enzymology, an ecdysone oxidase (EC number|1.1.3.16) is an enzyme that catalyzes the chemical reaction:ecdysone + O2 ightleftharpoons 3 dehydroecdysone + H2O2Thus, the two substrates of this enzyme are ecdysone and O2, whereas its two products … Wikipedia
ecdysone — also ecdyson noun Etymology: International Scientific Vocabulary ecdysis + hormone Date: 1956 any of several arthropod hormones that in insects are produced by the prothoracic gland and that trigger molting and metamorphosis … New Collegiate Dictionary

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Ecdysone

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