1.0 2010-04-08 22:07:28 UTC 2025-11-18 23:04:13 UTC FDB007162 Ecdysone Ecdysone, also known as molting hormone, belongs to pentahydroxy bile acids, alcohols and derivatives class of compounds. Those are bile acids, alcohols or derivatives bearing five hydroxyl groups. Thus, ecdysone is considered to be a sterol lipid molecule. Ecdysone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Ecdysone can be synthesized from 5beta-cholestane. Ecdysone is also a parent compound for other transformation products, including but not limited to, (25R)-11alpha,20,26-trihydroxyecdysone, (24R)-11alpha,20,24-trihydroxyecdysone, and ecdysone 25-O-D-glucopyranoside. Ecdysone can be found in spinach, which makes ecdysone a potential biomarker for the consumption of this food product. 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 in polytene chromosomes. Recent findings in Chris Q. Doe lab have found a novel role of this hormone in regulating temporal gene transitions within neural stem cells. Ecdysone and other 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 ecdysteroid precursor in plants has been shown to have cytotoxic properties. A pesticide sold with the name MIMIC has ecdysteroid activity, although its chemical structure has little resemblance to the ecdysteroids . 2beta,3beta,14alpha,22(R),25-Pentahydroxy-7-cholesten-6-one Alpha-ecdysone C27H44O6 464.6347 464.31378914 (1R,2R,4S,5R,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one (1R,2R,4S,5R,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one 3604-87-3 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=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 UPEZCKBFRMILAV-JMZLNJERSA-N belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups. Pentahydroxy bile acids, alcohols and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Aliphatic homopolycyclic compounds 14-hydroxysteroids 3-beta-hydroxysteroids 3-hydroxy delta-7-steroids 6-oxosteroids Cholesterols and derivatives Cyclic alcohols and derivatives Cyclohexenones Delta-7-steroids Ecdysteroids Hydrocarbon derivatives Organic oxides Polyols Secondary alcohols Tertiary alcohols 14-hydroxysteroid 2-hydroxysteroid 22-hydroxysteroid 25-hydroxysteroid 3-beta-hydroxysteroid 3-hydroxy-delta-7-steroid 3-hydroxysteroid 6-oxosteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Cholestane-skeleton Cholesterol Cholesterol-skeleton Cyclic alcohol Cyclohexenone Delta-7-steroid Ecdysteroid Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Pentahydroxy bile acid, alcohol, or derivatives Polyol Secondary alcohol Tertiary alcohol 14alpha-hydroxy steroid 22-hydroxy steroid 25-hydroxy steroid 2beta-hydroxy steroid 3beta-sterol 6-oxo steroid Cholestane and derivatives Cholesterol and derivatives Steroid hormones cholestane ecdysteroid logp 1.96 ALOGPS logs -3.47 ALOGPS solubility 1.58e-01 g/l ALOGPS logp 1.69 ChemAxon pka_strongest_acidic 13.51 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac (1R,2R,4S,5R,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one ChemAxon average_mass 464.6347 ChemAxon mono_mass 464.31378914 ChemAxon 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 ChemAxon formula C27H44O6 ChemAxon 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 ChemAxon inchikey UPEZCKBFRMILAV-JMZLNJERSA-N ChemAxon polar_surface_area 118.22 ChemAxon refractivity 127.42 ChemAxon polarizability 52.93 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1083833 Specdb::MsMs 54750 Specdb::MsMs 54751 Specdb::MsMs 54752 Specdb::MsMs 177906 Specdb::MsMs 177907 Specdb::MsMs 177908 23890 Spinach Type 1 specific Spinacia oleracea 3562 Anti gonadotrophic 307 Juvabional 1058 Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.