Ecdysone
PubChem CID: 19212
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| Compound Synonyms | ECDYSONE, alpha-Ecdysone, 3604-87-3, CCRIS 6931, EINECS 222-760-4, UNII-RH692X7B7B, (2beta,3beta,5beta,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-one, BRN 2422986, RH692X7B7B, CHEBI:16688, AI3-44726, ECDYSONE [MI], .ALPHA.-ECDYSONE, ECDYSONE, .ALPHA.-, 5-beta-Cholest-7-en-6-one, 2-beta,3-beta,14,22,25-pentahydroxy-, (20S,22R)-, 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, 4-08-00-03613 (Beilstein Handbook Reference), Cholest-7-en-6-one, 2,3,14,22,25-pentahydroxy-, (2.beta.,3.beta.,5.beta.,22R)-, a-Ecdysone ( >90%), Cholest-7-en-6-one, 2,3,14,22,25-pentahydroxy-, (2beta,3beta,5beta,22R)-, Cholest-7-en-6-one, 2,3,14,22,25-pentahydroxy-, (2-beta,3-beta,5-beta,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, (22R)-2beta,3beta,14,22,25-pentahydroxy-5beta-cholest-7-en-6-one, (2.BETA.,3.BETA.,5.BETA.,22R)-2,3,14,22,25-PENTAHYDROXYCHOLEST-7-EN-6-ONE, DTXSID2020553, (2ss,3ss,5ss,22R)-2,3,14,22,25-pentahydroxycholest-7-en-6-one, -Ecdysone, (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, A-ECDYSONE, ECDYSONE, ALPHA-, Cholest-7-en-6-one, 2,3,14,22,25-pentahydroxy-, (2b,3b,5b,22R)-, alpha-Ecdysone, >=90%, Alpha-Ecdysone ( >90%), SCHEMBL23780, DTXCID40553, CHEMBL549300, BCBcMAP01_000123, HY-N0179, alpha-Ecdysone, >=99.0% (UV), HB3881, LMST01010210, MFCD00042683, AKOS015951280, CCG-208571, FE71507, SMP1_000109, CS-0007889, NS00029970, C00477, G12108, Q139085, SR-05000002190, SR-05000002190-3, 2b,3b,14a,22(R),25-Pentahydroxy-7-cholesten-6-one, (22R)-2b,3b,14,22,25-Pentahydroxy-5b-cholest-7-en-6-one, (22R)-2b,3b,14a,22,25-Pentahydroxy-5b-cholest-7-en-6-one, 2beta,3beta,14alpha,22(R),25-Pentahydroxy-7-cholesten-6-one, 7, (5alpha)-Cholesten-2beta, 3beta, 14alpha, 22r, 25-pentol-6-one, Cholest-7-en-6-one, 2,3,14,22,25-pentahydroxy-, (2-beta,3-beta,5-beta,22R)-(9CI), (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-2,3,4,5,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6(10H)-one |
|---|---|
| Ghose Rule | False |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 118.0 |
| Hydrogen Bond Donor Count | 5.0 |
| Pfizer 3 75 Rule | True |
| Scaffold Graph Level | CC1CC2C3CCCC3CCC2C2CCCCC12 |
| Np Classifier Class | Ecdysteroids |
| Deep Smiles | O[C@@H][C@H][C@H]CC[C@@][C@]5C)CC[C@H]C6=CC=O)[C@H][C@]6C)C[C@H]O)[C@@H]C6)O)))))))))))))O)))))C))CCCO)C)C |
| Heavy Atom Count | 33.0 |
| Classyfire Class | Steroids and steroid derivatives |
| Description | 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 . |
| Scaffold Graph Node Level | OC1CC2C3CCCC3CCC2C2CCCCC12 |
| Classyfire Subclass | Bile acids, alcohols and derivatives |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 821.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 10.0 |
| Uniprot Id | P34021, P08183, O42275, P81908, E5L6Y0 |
| 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 |
| Prediction Hob | 0.0 |
| Veber Rule | True |
| Classyfire Superclass | Lipids and lipid-like molecules |
| Xlogp | 1.7 |
| Gsk 4 400 Rule | False |
| Molecular Formula | C27H44O6 |
| Scaffold Graph Node Bond Level | O=C1C=C2C3CCCC3CCC2C2CCCCC12 |
| Prediction Swissadme | 1.0 |
| Inchi Key | UPEZCKBFRMILAV-JMZLNJERSA-N |
| Silicos It Class | Soluble |
| Fcsp3 | 0.8888888888888888 |
| Logs | -3.262 |
| Rotatable Bond Count | 5.0 |
| Logd | 1.626 |
| Synonyms | 2beta,3beta,14alpha,22(R),25-Pentahydroxy-7-cholesten-6-one, Alpha-ecdysone, alpha-ecdysone, ecdysone |
| Esol Class | Soluble |
| Functional Groups | CC(C)=CC(C)=O, CO |
| Compound Name | Ecdysone |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 464.314 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 464.314 |
| Hydrogen Bond Acceptor Count | 6.0 |
| Molecular Weight | 464.6 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 10.0 |
| Total Bond Stereocenter Count | 0.0 |
| Lipinski Rule Of 5 | True |
| Esol | -3.4554866000000013 |
| 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 |
| 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 |
| Nring | 4.0 |
| Np Classifier Biosynthetic Pathway | Terpenoids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Np Classifier Superclass | Steroids |
- 1. Outgoing r'ship
FOUND_INto/from Achyranthes Aspera (Plant) Rel Props:Reference:The Ayurvedic Pharmacopoeia of India Part-1 Volume-9 - 2. Outgoing r'ship
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FOUND_INto/from Attalea Excelsa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
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FOUND_INto/from Silene Vulgaris (Plant) Rel Props:Reference:ISBN:9788185042138 - 25. Outgoing r'ship
FOUND_INto/from Spinacia Oleracea (Plant) Rel Props:Source_db:fooddb_chem_all - 26. Outgoing r'ship
FOUND_INto/from Tanacetum Parthenifolium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all