(8S,9S,10R,13S,14S)-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
PubChem CID: 13783449
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| Compound Synonyms | 11-Oxocorticosterone, Dehydrocortocicosterone, (8S,9S,10R,13S,14S)-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11-dione, 11-dehydro-Corticosterone, D4-Pregnen-21-ol-3,11,20-trione, D4-Pregnene-21-ol-3,11,20-trione, 17-deoxy cortisone, 17-(1-keto-2-Hydroxyethyl)-D4-androsten-3,11-dione, SCHEMBL141611, LMST02030192 |
|---|---|
| Topological Polar Surface Area | 71.4 |
| Hydrogen Bond Donor Count | 1.0 |
| Heavy Atom Count | 25.0 |
| Pathway Kegg Map Id | map00140 |
| Description | 11-Dehydrocorticosterone is a mineral corticosteroid. The conversion of inactive 11-ketoglucocorticoids such as 11-dehydrocorticosterone) into active 11b-hydroxyglucocorticoids (such as corticosterone) is catalyzed by 11beta-hydroxysteroid dehydrogenase (11b-HSD1, EC 1.1.1.146), which is expressed in many tissues and plays an important role in metabolically relevant tissues such as the liver, adipose tissue, skeletal muscles and possibly kidney. Chronically elevated local glucocorticoid action as a result of increased 11beta-HSD1 activity rather than elevated systemic glucocorticoid levels has been associated with metabolic syndrome, which is characterized by obesity, insulin resistance, type 2 diabetes and cardiovascular complications. Recent studies indicate that compounds inhibiting 11beta-HSD1 activity ameliorate the adverse effects of excessive glucocorticoid concentrations on metabolic processes, providing promising opportunities for the development of therapeutic interventions. 11-dehydrocorticosterone and corticosterone display antinatriuretic activity, although 11-dehydrocorticosterone is generally a more potent sodium retainer than corticosterone. (PMID: 17584152, Endocr Metab Immune Disord Drug Targets. 2007 Jun, 7(2):125-40.) [HMDB] |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 677.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;pubchem |
| Defined Atom Stereocenter Count | 5.0 |
| Enzyme Uniprot Id | P51857, P28845 |
| Iupac Name | (8S,9S,10R,13S,14S)-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11-dione |
| Prediction Hob | 1.0 |
| Class | Steroids and steroid derivatives |
| Xlogp | 1.8 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Hydroxysteroids |
| Molecular Formula | C21H28O4 |
| Prediction Swissadme | 1.0 |
| Inchi Key | FUFLCEKSBBHCMO-IWBQTIMDSA-N |
| Fcsp3 | 0.7619047619047619 |
| Logs | -3.095 |
| Rotatable Bond Count | 2.0 |
| State | Solid |
| Logd | 0.896 |
| Synonyms | 11-dehydro-Corticosterone, 11-Dehydrocorticosteron, 11-Dehydrocorticosterone, 11-Oxo-11-deoxycorticosterone, 11-Oxocorticosterone, 17-(1-keto-2-Hydroxyethyl)-D4-androsten-3,11-dione, 17-Deoxycortisone, 21-Hydroxypregn-4-ene-3,11-20-trione, 21-Hydroxypregn-4-ene-3,11,20-trione, 4-Pregnen-21-ol-3,11,20-trione, D4-Pregnen-21-ol-3,11,20-trione, D4-Pregnene-21-ol-3,11,20-trione, Dehydrocorticosterone, Dehydrocortocicosterone, Kendall's compound A |
| Substituent Name | 21-hydroxysteroid, Progestogin-skeleton, Pregnane-skeleton, 20-oxosteroid, Oxosteroid, 11-oxosteroid, 3-oxosteroid, 3-oxo-delta-4-steroid, Delta-4-steroid, Cyclohexanone, Alpha-hydroxy ketone, Cyclic ketone, Ketone, Hydrocarbon derivative, Primary alcohol, Organooxygen compound, Carbonyl group, Alcohol, Aliphatic homopolycyclic compound |
| Compound Name | (8S,9S,10R,13S,14S)-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11-dione |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 1.0 |
| Exact Mass | 344.199 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 344.199 |
| Hydrogen Bond Acceptor Count | 4.0 |
| Molecular Weight | 344.4 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 6.0 |
| Total Bond Stereocenter Count | 0.0 |
| Esol | -2.9586962000000003 |
| Inchi | InChI=1S/C21H28O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-16,19,22H,3-8,10-11H2,1-2H3/t14-,15-,16?,19+,20-,21-/m0/s1 |
| Smiles | C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CCC4C(=O)CO)C |
| Nring | 4.0 |
| Defined Bond Stereocenter Count | 0.0 |
- 1. Outgoing r'ship
FOUND_INto/from Chrysanthemum Lavandulifolium (Plant) Rel Props:Source_db:cmaup_ingredients