Hydrocortisone
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Basic Info
| Common Name | Hydrocortisone(F06165) |
| 2D Structure | |
| FRCD ID | F06165 |
| CAS Number | 50-23-7 |
| PubChem CID | 5754 |
| Formula | C21H30O5 |
| IUPAC Name | (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one |
| InChI Key | JYGXADMDTFJGBT-VWUMJDOOSA-N |
| InChI | InChI=1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1 |
| Canonical SMILES | CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4(C(=O)CO)O)C)O |
| Isomeric SMILES | C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O |
| Synonyms |
hydrocortisone
Cortef
Cortisol
50-23-7
Acticort
Cetacort
Hydrocortisyl
Cobadex
Hydrasson
Hycort
|
| Classifies |
Predicted: 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 - 20-oxosteroid - Pregnane-skeleton - 3-oxo-delta-4-steroid - 3-oxosteroid - Oxosteroid - 11-beta-hydroxysteroid - 11-hydroxysteroid - 17-hydroxysteroid - Delta-4-steroid - Cyclohexenone - Cyclic alcohol - Tertiary alcohol - Alpha-hydroxy ketone - Secondary alcohol - Ketone - Cyclic ketone - Primary alcohol - Alcohol - Organooxygen compound - Organic oxide - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - 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 | 362.466 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 2 |
| Complexity | 684 |
| Monoisotopic Mass | 362.209 |
| Exact Mass | 362.209 |
| XLogP | 1.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 26 |
| Defined Atom Stereocenter Count | 7 |
| 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+ | 0.9383 |
| Human Intestinal Absorption | HIA+ | 0.9918 |
| Caco-2 Permeability | Caco2- | 0.5096 |
| P-glycoprotein Substrate | Substrate | 0.7861 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7847 |
| Non-inhibitor | 0.8383 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7463 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8362 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8496 |
| CYP450 2D6 Substrate | Non-substrate | 0.9138 |
| CYP450 3A4 Substrate | Substrate | 0.7407 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9406 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9072 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9418 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9253 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8902 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9095 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9500 |
| Non-inhibitor | 0.5840 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.9597 |
| Fish Toxicity | High FHMT | 0.9833 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9848 |
| Honey Bee Toxicity | High HBT | 0.7998 |
| Biodegradation | Not ready biodegradable | 0.9250 |
| Acute Oral Toxicity | III | 0.7997 |
| Carcinogenicity (Three-class) | Non-required | 0.7360 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.0321 | LogS |
| Caco-2 Permeability | 0.8616 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8914 | LD50, mol/kg |
| Fish Toxicity | 1.0228 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.9935 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Milk | United States | 10ppb | |||
| Milk | Japan | 0.01ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Effect of 17β-estradiol on milk production, hormone secretion, and mammary gland gene expression in dairy cows. | J Dairy Sci | 2018 Mar | 29274969 |
| Postpartum ketoprofen treatment does not alter stress biomarkers in cows andcalves experiencing assisted and unassisted parturition: a randomised controlled trial. | Vet Rec | 2018 Jun 30 | 29960984 |
| Periparturient Behavior and Physiology: Further Insight Into the FarrowingProcess for Primiparous and Multiparous Sows. | Front Vet Sci | 2018 Jun 12 | 29946552 |
| Physiological impacts and bioaccumulation of dietary Cu and Cd in a modelteleost: The Amazonian tambaqui (Colossoma macropomum). | Aquat Toxicol | 2018 Jun | 29604500 |
| Comparative study of two different chromatographic approaches for quantitation of hydrocortisone acetate and pramoxine hydrochloride in presence of their impurities. | J Food Drug Anal | 2018 Jul | 29976408 |
| Energy Expenditure and Hormone Responses in Humans After Overeating High-FructoseCorn Syrup Versus Whole-Wheat Foods. | Obesity (Silver Spring) | 2018 Jan | 29193741 |
| Effects of gradual reduction in frequency of energy supplementation on growth andimmunity of beef steers. | J Anim Sci | 2018 Feb 15 | 29385600 |
| Effects of timing of vaccination relative to weaning and post-weaning frequencyof energy supplementation on growth and immunity of beef calves. | J Anim Sci | 2018 Feb 15 | 29378006 |
| The impact of exertional-heat stress on gastrointestinal integrity, gastrointestinal symptoms, systemic endotoxin and cytokine profile. | Eur J Appl Physiol | 2018 Feb | 29234915 |
| Adrenal cortex reactivity in dairy cows differs between lactational stages andbetween different feeding levels. | J Anim Physiol Anim Nutr (Berl) | 2018 Feb | 28504317 |
| Glucan-MOS® improved growth and innate immunity in pacu stressed andexperimentally infected with Aeromonas hydrophila. | Fish Shellfish Immunol | 2018 Feb | 29191795 |
| Ethnopharmacology of Love. | Front Pharmacol | 2018 | 30026695 |
| Effects of Chromium Methionine Supplementation with Different Sources of Zinc on Growth Performance, Carcass Traits, Meat Quality, Serum Metabolites, EndocrineParameters, and the Antioxidant Status in Growing-Finishing Pigs. | Biol Trace Elem Res | 2017 Sep | 28108862 |
| Differential expression of glucagon-like peptide-2 (GLP-2) is involved inpancreatic islet cell adaptations to stress and beta-cell survival. | Peptides | 2017 Sep | 28746825 |
| Link between cutaneous infection, stress and depression. | J Biol Regul Homeost Agents | 2017 Oct-Dec | 29254311 |
| A meta-analysis of cortisol concentration, vocalization, and average daily gainassociated with castration in beef cattle. | Res Vet Sci | 2017 Oct | 28755556 |
| Effects of chronic exposure to dietary selenomethionine on the physiological stress response in juvenile white sturgeon (Acipenser transmontanus). | Aquat Toxicol | 2017 May | 28260669 |
| Hepatic mRNA expression for genes related to somatotropic axis, glucose and lipidmetabolisms, and inflammatory response of periparturient dairy cows treated with recombinant bovine somatotropin. | J Dairy Sci | 2017 May | 28237587 |
| Dietary zinc promotes immuno-biochemical plasticity and protects fish againstmultiple stresses. | Fish Shellfish Immunol | 2017 Mar | 28108338 |
| Effects of intrauterine infusion of Escherichia coli lipopolysaccharide on uterine mRNA gene expression and peripheral polymorphonuclear leukocytes in Jersey cows diagnosed with purulent vaginal discharge. | J Dairy Sci | 2017 Jun | 28434729 |