Alpha-Ecdysone
From DrugPedia: A Wikipedia for Drug discovery
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| - | + | [http://crdd.osdd.net/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1052&show=SHOW-3D Show 3-D Structure] | |
| - | [http:// | + | {{Drugbox |
| - | + | | 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 | |
| + | | CAS_number = 3604-87-3 | ||
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| + | | PubChem = 19212 | ||
| + | | ChemSpiderID = | ||
| + | | chemical_formula =C<sub>2</sub><sub>7</sub>H<sub>4</sub><sub>4</sub>O<sub>6</sub> | ||
| + | | molecular_weight = 464.63 | ||
| + | | smiles = CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(C)O)O | ||
| + | | synonyms = Ecdysone | ||
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A steroid hormone that regulates the processes of MOLTING or ecdysis in insects. | A steroid hormone that regulates the processes of MOLTING or ecdysis in insects. | ||
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| + | '''Ecdysone''' is a [[steroid]]al [[prohormone]] of the major insect [[ecdysis|molting]] hormone [[20-hydroxyecdysone]], which is secreted from the [[prothoracic gland]]s. Insect molting hormones (ecdysone and its homologues) are generally called [[ecdysteroid]]s. Ecdysteroids act as moulting hormones of [[arthropod]]s 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 [[phytoecdysteroid]]s have medicinal value{{Fact|date=April 2008}} and are part of herbal [[adaptogen]]ic remedies like [[Cordyceps]]. A pesticide sold with the name MIMIC has ecdysteroid activity, although its chemical structure has little resemblance to the ecdysteroids. | ||
==General Properties== | ==General Properties== | ||
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C[C@@H]([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)[C@@H](CCC(C)(C)O)O | C[C@@H]([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)[C@@H](CCC(C)(C)O)O | ||
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*[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=19212]Pubchem | *[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=19212]Pubchem | ||
*[http://www.genome.jp/dbget-bin/www_bget?compound+C00477]KEGG Compound | *[http://www.genome.jp/dbget-bin/www_bget?compound+C00477]KEGG Compound | ||
| + | * [http://ecdybase.org/ Ecdybase], The Ecdysone Handbook - a free online ecdysteroids database | ||
| - | + | [[Category:Hormones]] | |
| - | [[ | + | [[Category:Entomology]] |
| + | [[Category:Steroids]] | ||
Current revision
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| Alpha-Ecdysone
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| Systematic (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 | |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C27H44O6 |
| Mol. mass | 464.63 |
| SMILES | & |
| Synonyms | Ecdysone |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
A steroid hormone that regulates the processes of MOLTING or ecdysis in insects.
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 medicinal valueTemplate:Fact and are part of herbal adaptogenic remedies like Cordyceps. A pesticide sold with the name MIMIC has ecdysteroid activity, although its chemical structure has little resemblance to the ecdysteroids.
[edit] General Properties
*Molecular Weight
464.63
*Molecular Formula
C27H44O6
*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
*Canonical Smiles
CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(C)O)O
*Isomeric Smiles
C[C@@H]([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)[C@@H](CCC(C)(C)O)O
