Deoxycorticosterone
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Basic Info
| Common Name | Deoxycorticosterone(F05299) |
| 2D Structure | |
| Description | Deoxycorticosterone is a steroid or mineralocorticoid secreted by the zona fasiculata of the adrenal cortex. Deoxycorticsterone acts as a precursor to aldosterone. Deoxycorticosterone is not a major secretory hormone. It is produced from progesterone by 21beta-hydroxylase and is converted to corticosterone by 11beta-hydroxylase. Corticosterone is then converted to aldosterone by aldosterone synthase. Deoxycorticosterone stimulates the collecting tubules in the kidney to continue to excrete potassium in much the same way that aldosterone does. Deoxycorticosterone has about 1/20 of the sodium retaining power of aldosterone and about 1/5 the potassium excreting power of aldosterone . Deoxycorticosterone can be used to treat adrenal insufficiency. In particular, desoxycorticosterone acetate (DOCA) is used as replacement therapy in Addison's disease. |
| FRCD ID | F05299 |
| CAS Number | 64-85-7 |
| PubChem CID | 6166 |
| Formula | C21H30O3 |
| IUPAC Name | (8S,9S,10R,13S,14S,17S)-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one |
| InChI Key | ZESRJSPZRDMNHY-YFWFAHHUSA-N |
| InChI | InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1 |
| Canonical SMILES | CC12CCC3C(C1CCC2C(=O)CO)CCC4=CC(=O)CCC34C |
| Isomeric SMILES | C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)CO)CCC4=CC(=O)CC[C@]34C |
| Wikipedia | Deoxycorticosterone |
| Synonyms |
Desoxycortone
64-85-7
21-Hydroxyprogesterone
desoxycorticosterone
11-Deoxycorticosterone
Deoxycorticosterone
Cortexone
Deoxycortone
11-Desoxycorticosterone
Reichstein's substance Q
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Steroids and steroid derivatives |
| Subclass | Hydroxysteroids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | 21-hydroxysteroids |
| Alternative Parents | |
| Molecular Framework | Aliphatic homopolycyclic compounds |
| Substituents | Progestogin-skeleton - 21-hydroxysteroid - Pregnane-skeleton - 20-oxosteroid - 3-oxo-delta-4-steroid - 3-oxosteroid - Oxosteroid - Delta-4-steroid - Cyclohexenone - Alpha-hydroxy ketone - Cyclic ketone - Ketone - Organic oxygen compound - Organooxygen compound - Primary alcohol - Carbonyl group - Hydrocarbon derivative - Alcohol - Organic oxide - Aliphatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 330.468 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Complexity | 606 |
| Monoisotopic Mass | 330.219 |
| Exact Mass | 330.219 |
| XLogP | 2.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 24 |
| Defined Atom Stereocenter Count | 6 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9754 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8590 |
| P-glycoprotein Substrate | Substrate | 0.6433 |
| P-glycoprotein Inhibitor | Inhibitor | 0.6354 |
| Non-inhibitor | 0.6433 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.6172 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8619 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8156 |
| CYP450 2D6 Substrate | Non-substrate | 0.9122 |
| CYP450 3A4 Substrate | Substrate | 0.7451 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9070 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9231 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9123 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8070 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9163 |
| Non-inhibitor | 0.6030 | |
| AMES Toxicity | Non AMES toxic | 0.9236 |
| Carcinogens | Non-carcinogens | 0.9398 |
| Fish Toxicity | High FHMT | 0.9796 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9574 |
| Honey Bee Toxicity | High HBT | 0.8081 |
| Biodegradation | Not ready biodegradable | 0.9494 |
| Acute Oral Toxicity | III | 0.7315 |
| Carcinogenicity (Three-class) | Non-required | 0.6032 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.6875 | LogS |
| Caco-2 Permeability | 1.4737 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.3868 | LD50, mol/kg |
| Fish Toxicity | 0.6671 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.0354 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Mercury in fish from Norwegian lakes: The complex influence of aqueous organiccarbon. | Sci Total Environ | 2018 Jun 15 | 29426157 |
| Derivation of reliable empirical models describing lead transfer frommetal-polluted soils to radish (Raphanus sativa L.): Determining factors and soilcriteria. | Sci Total Environ | 2018 Feb 1 | 28903078 |
| Trace metals partitioning between particulate and dissolved phases along atropical mangrove estuary (Can Gio, Vietnam). | Chemosphere | 2018 Apr | 29306784 |
| Microbial parasites make cyanobacteria blooms less of a trophic dead end thancommonly assumed. | ISME J | 2018 Apr | 29416126 |
| Nickel toxicity to benthic organisms: The role of dissolved organic carbon,suspended solids, and route of exposure. | Environ Pollut | 2016 Jan | 26552544 |
| Antibiotic susceptibility of Legionella strains isolated from public watersources in Macau and Guangzhou. | J Water Health | 2016 Dec | 27959883 |
| Distribution of rare earth elements in soil and grape berries of Vitis viniferacv. "Glera". | Environ Monit Assess | 2016 Aug | 27447714 |
| Risk of Introduction in Northern Vietnam of HPAI Viruses from China: Description,Patterns and Drivers of Illegal Poultry Trade. | Transbound Emerg Dis | 2016 Aug | 25268992 |
| Evaluation of TPGS-modified thermo-sensitive Pluronic PF127 hydrogel as apotential carrier to reverse the resistance of P-gp-overexpressing SMMC-7721 celllines. | Colloids Surf B Biointerfaces | 2016 Apr 1 | 26764117 |
| Combined photo-fenton-SBR processes for the treatment of wastewater from thecitrus processing industry. | J Agric Food Chem | 2015 Jan 21 | 25531123 |
| The first insight into the metabolite profiling of grapes from three Vitisvinifera L. cultivars of two controlled appellation (DOC) regions. | Int J Mol Sci | 2014 Mar 10 | 24619195 |
| Bioturbation/bioirrigation by Chironomus plumosus as main factor controllingelemental remobilization from aquatic sediments? | Chemosphere | 2014 Jul | 24457053 |
| Decrease of concentration and colloidal fraction of organic carbon and traceelements in response to the anomalously hot summer 2010 in a humic boreal lake. | Sci Total Environ | 2013 Oct 1 | 23792250 |
| Toxicity of synthetic chelators and metal availability in poultry manure amended Cd, Pb and As contaminated agricultural soil. | J Hazard Mater | 2013 Nov 15 | 23791533 |
| Mechanisms of waterborne Cu toxicity to the pond snail Lymnaea stagnalis:physiology and Cu bioavailability. | Ecotoxicol Environ Saf | 2011 Sep | 21783254 |
| Protectiveness of water quality criteria for copper in western United Stateswaters relative to predicted olfactory responses in juvenile Pacific salmon. | Integr Environ Assess Manag | 2011 Jul | 21120904 |
| Comparative sorption and leaching study of the herbicides fluometuron and4-chloro-2-methylphenoxyacetic acid (MCPA) in a soil amended with biochars andother sorbents. | J Agric Food Chem | 2011 Dec 14 | 22023336 |
| Incidence of tetracycline residues in chicken meat and liver retailed toconsumers. | Food Addit Contam Part B Surveill | 2011 | 24785718 |
| Effect of dissolved organic matters on napropamide availability and ecotoxicityin rapeseed ( Brassica napus ). | J Agric Food Chem | 2010 Mar 10 | 20143852 |
| Major role of microbes in carbon fluxes during Austral winter in the SouthernDrake Passage. | PLoS One | 2009 Sep 14 | 19759822 |
Targets
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelacortin neurons and the release of CRH that then regulates the release of corticosterone. Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress. Plays a role in insulin sensitivity and glucose homeostasis.
- Gene Name:
- HTR2C
- Uniprot ID:
- P28335
- Molecular Weight:
- 51820.705 Da
References
- Nelson DL, Lucaites VL, Wainscott DB, Glennon RA: Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors. Naunyn Schmiedebergs Arch Pharmacol. 1999 Jan;359(1):1-6. [9933142 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Krishnan AV, Zhao XY, Swami S, Brive L, Peehl DM, Ely KR, Feldman D: A glucocorticoid-responsive mutant androgen receptor exhibits unique ligand specificity: therapeutic implications for androgen-independent prostate cancer. Endocrinology. 2002 May;143(5):1889-900. [11956172 ]
- General Function:
- Androgen binding
- Specific Function:
- Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration.
- Gene Name:
- SHBG
- Uniprot ID:
- P04278
- Molecular Weight:
- 43778.755 Da
References
- Cherkasov A, Ban F, Santos-Filho O, Thorsteinson N, Fallahi M, Hammond GL: An updated steroid benchmark set and its application in the discovery of novel nanomolar ligands of sex hormone-binding globulin. J Med Chem. 2008 Apr 10;51(7):2047-56. doi: 10.1021/jm7011485. Epub 2008 Mar 11. [18330978 ]
- General Function:
- Virus receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction.(Microbial infection) Acts as a receptor for human JC polyomavirus/JCPyV.
- Gene Name:
- HTR2A
- Uniprot ID:
- P28223
- Molecular Weight:
- 52602.58 Da
References
- Nelson DL, Lucaites VL, Wainscott DB, Glennon RA: Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors. Naunyn Schmiedebergs Arch Pharmacol. 1999 Jan;359(1):1-6. [9933142 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of dopamine and 5-hydroxytryptamine release, 5-hydroxytryptamine uptake and in the regulation of extracellular dopamine and 5-hydroxytryptamine levels, and thereby affects neural activity. May play a role in the perception of pain. Plays a role in the regulation of behavior, including impulsive behavior. Required for normal proliferation of embryonic cardiac myocytes and normal heart development. Protects cardiomyocytes against apoptosis. Plays a role in the adaptation of pulmonary arteries to chronic hypoxia. Plays a role in vasoconstriction. Required for normal osteoblast function and proliferation, and for maintaining normal bone density. Required for normal proliferation of the interstitial cells of Cajal in the intestine.
- Gene Name:
- HTR2B
- Uniprot ID:
- P41595
- Molecular Weight:
- 54297.41 Da
References
- Nelson DL, Lucaites VL, Wainscott DB, Glennon RA: Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors. Naunyn Schmiedebergs Arch Pharmacol. 1999 Jan;359(1):1-6. [9933142 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth. Involved in chromatin remodeling. May play a negative role in adipogenesis through the regulation of lipolytic and antilipogenic genes expression.
- Gene Name:
- NR3C1
- Uniprot ID:
- P04150
- Molecular Weight:
- 85658.57 Da
References
- Krishnan AV, Zhao XY, Swami S, Brive L, Peehl DM, Ely KR, Feldman D: A glucocorticoid-responsive mutant androgen receptor exhibits unique ligand specificity: therapeutic implications for androgen-independent prostate cancer. Endocrinology. 2002 May;143(5):1889-900. [11956172 ]