Compound: ECDYSONE
SMILES: O=C1C=C2[C@@]3(O)[C@@]([C@@H]([C@@H]([C@H](O)CCC(O)(C)C)C)CC3)(CC[C@@H]2[C@@]4([C@H]1C[C@@H](O)[C@H](C4)O)C)C
InChIKey: UPEZCKBFRMILAV-JMZLNJERSA-N
Synonyms: ECDYSONE, (2beta,3beta,5beta,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-one, RH692X7B7B, CHEBI:16688, 2beta,3beta,14alpha,22R,25-pentahydroxy-5beta-cholest-7-en-6-one, (22R)-2beta,3beta,14alpha,22,25-pentahydroxy-5beta-cholest-7-en-6-one, Cholest-7-en-6-one, 2,3,14,22,25-pentahydroxy-, (2beta,3beta,5beta,22R)-, (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, (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, RefChem:136201, 222-760-4, alpha-Ecdysone, 3604-87-3, 5-beta-Cholest-7-en-6-one, 2-beta,3-beta,14,22,25-pentahydroxy-, (20S,22R)-, a-Ecdysone ( >90%), Cholest-7-en-6-one, 2,3,14,22,25-pentahydroxy-, (2.beta.,3.beta.,5.beta.,22R)-, CCRIS 6931, EINECS 222-760-4, BRN 2422986, UNII-RH692X7B7B, (2ss,3ss,5ss,22R)-2,3,14,22,25-pentahydroxycholest-7-en-6-one, AI3-44726, -Ecdysone, |_-Ecdysone, A-ECDYSONE, ECDYSONE [MI], .ALPHA.-ECDYSONE, Cholest-7-en-6-one, 2,3,14,22,25-pentahydroxy-, (2b,3b,5b,22R)-, alpha-Ecdysone, >=90%, ECDYSONE, .ALPHA.-, SCHEMBL23780, 4-08-00-03613 (Beilstein Handbook Reference), CHEMBL549300, BCBcMAP01_000123, GLXC-21718, HY-N0179, (22R)-2beta,3beta,14,22,25-pentahydroxy-5beta-cholest-7-en-6-one, alpha-Ecdysone, >=99.0% (UV), HB3881, LMST01010210, AKOS015951280, CCG-208571, FE71507, Cholest-7-en-6-one, 2,3,14,22,25-pentahydroxy-, (2-beta,3-beta,5-beta,22R)-, SMP1_000109, CS-0007889, NS00029970, C00477, G12108, Q139085, SR-05000002190, SR-05000002190-3, 2b,3b,14a,22(R),25-Pentahydroxy-7-cholesten-6-one, (2.BETA.,3.BETA.,5.BETA.,22R)-2,3,14,22,25-PENTAHYDROXYCHOLEST-7-EN-6-ONE, (2S,3R,5R,9R,10R,13R,14S,17R)-17-[(1S,2R)-2,5-dihydroxy-1,5-dimethyl-hexyl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Theoretical properties:
molecular_formula: C27H44O6
molecular_weight: 464.6 g/mol
exact_mass: 464.31378912 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 5
heavy_atom_count: 33
topological_polar_surface_area: 118 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Ecdysone is a 6-oxo steroid that is 5beta-cholest-7-en-6-one substituted by hydroxy groups at positions 2, 3, 14, 22 and 25 respectively (the 2beta, 3beta, 22R stereoisomer). It is a steroid prohormone of the major insect moulting hormone 20-hydroxyecdysone. It has a role as a prohormone. It is an ecdysteroid, a 3beta-sterol, a 2beta-hydroxy steroid, a 14alpha-hydroxy steroid, a 22-hydroxy steroid, a 25-hydroxy steroid and a 6-oxo steroid. It derives from a hydride of a 5beta-cholestane.", "chebi": "A 6-oxo steroid that is 5\u03b2-cholest-7-en-6-one substituted by hydroxy groups at positions 2, 3, 14, 22 and 25 respectively (the 2\u03b2, 3\u03b2, 22<i>R</i> stereoisomer). It is a steroid prohormone of the major insect moulting hormone 20-hydroxyecdysone.", "chembl": "ECDYSONE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Ecdysone is a prohormone of the major insect molting hormone 20-hydroxyecdysone, secreted from the prothoracic glands. It is of steroidal structure. 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. It causes chromosome puffs (sites of high expression) to form in polytene chromosomes. Recent findings in the laboratory of Chris Q. Doe have found a novel role of this hormone in regulating temporal gene transitions within neural stem cells of the fruit fly. \nEcdysone and other ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects. Some phytoecdysteroids may be bioactive in human contexts such as n ecdysteroid precursor from Stachyurus himalaicus, which exhibits cytotoxicity  Ecdysones from insects have also exhibited antioxidant properties on lipid peroxidation.. Ecdysteroids are also found in the purport adaptogen Cordyceps militaris . \nTebufenozide, sold under the Bayer trademark MIMIC, has ecdysteroid activity although it bears little resemblance to the ecdysteroids."}