| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:01:39 UTC |
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| Update Date | 2020-05-11 20:57:10 UTC |
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| BMDB ID | BMDB0002802 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Cortisone |
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| Description | Cortisonee, also known as cortisone or cortisone, 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. Thus, cortisonee is considered to be a steroid lipid molecule. Cortisonee exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Cortisonee participates in a number of enzymatic reactions, within cattle. In particular, Cortisonee can be biosynthesized from 17a,21-dihydroxy-5b-pregnane-3,11,20-trione; which is mediated by the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. In addition, Cortisonee, nadph, and hydrogen ion can be biosynthesized from cortisol and nadp through its interaction with the enzyme corticosteroid 11-beta-dehydrogenase isozyme 2. In cattle, cortisonee is involved in the metabolic pathway called the steroidogenesis pathway. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 11-Dehydro-17-hydroxycorticosterone | ChEBI | | 17-Hydroxy-11-dehydrocorticosterone | ChEBI | | 17alpha,21-Dihydroxy-4-pregnene-3,11,20-trione | ChEBI | | 4-Pregnene-17alpha,21-diol-3,11,20-trione | ChEBI | | Cortison | ChEBI | | Delta(4)-Pregnene-17alpha,21-diol-3,11,20-trione | ChEBI | | Kendall's compound e | ChEBI | | Kortison | ChEBI | | Pregn-4-en-17alpha,21-diol-3,11,20-trione | ChEBI | | Reichstein's substance fa | ChEBI | | Wintersteiner's compound F | ChEBI | | 17a,21-Dihydroxy-4-pregnene-3,11,20-trione | Generator | | 17Α,21-dihydroxy-4-pregnene-3,11,20-trione | Generator | | 4-Pregnene-17a,21-diol-3,11,20-trione | Generator | | 4-Pregnene-17α,21-diol-3,11,20-trione | Generator | | delta(4)-Pregnene-17a,21-diol-3,11,20-trione | Generator | | Δ(4)-pregnene-17α,21-diol-3,11,20-trione | Generator | | Pregn-4-en-17a,21-diol-3,11,20-trione | Generator | | Pregn-4-en-17α,21-diol-3,11,20-trione | Generator | | Δ(4)-pregnene-17a,21-diol-3,11,20-trione | HMDB | | Andreson | HMDB | | Anusol HC | HMDB | | Balneol-HC | HMDB | | beta-HC | HMDB | | Colocort | HMDB | | Compound e | HMDB | | Corlin | HMDB | | Cortadren | HMDB | | Cortandren | HMDB | | Cortef | HMDB | | Cortef acetate | HMDB | | Cortisal | HMDB | | Cortisate | HMDB | | Cortisone acetate | HMDB | | Cortistal | HMDB | | Cortivite | HMDB | | Cortogen | HMDB | | Cortone | HMDB | | Cortril | HMDB | | Dermacort | HMDB | | Dricort | HMDB | | Flexicort | HMDB | | Florinef | HMDB | | Fludrocortisone acetate | HMDB | | Glycort | HMDB | | Hemsol-HC | HMDB | | Hi-cor | HMDB | | Incortin | HMDB | | Kendall'S compound | HMDB | | Locoid | HMDB | | Locoid lipocream | HMDB | | Micort-HC | HMDB | | Nogenic HC | HMDB | | Orabase hca | HMDB | | Pandel | HMDB | | Prestwick_132 | HMDB | | Reichstein fa | HMDB | | Scheroson | HMDB | | Solu-cortef | HMDB | | Stie-cort | HMDB | | Texacort | HMDB | | Westcort | HMDB | | Adreson | HMDB | | Cortone acetate | HMDB | | 17-Hydroxy-3,11,20-trioxopregn-4-en-21-yl acetate | HMDB |
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| Chemical Formula | C21H28O5 |
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| Average Molecular Weight | 360.444 |
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| Monoisotopic Molecular Weight | 360.193674006 |
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| IUPAC Name | (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione |
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| Traditional Name | (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione |
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| CAS Registry Number | 53-06-5 |
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| SMILES | [H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C |
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| InChI Identifier | InChI=1S/C21H28O5/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/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1 |
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| InChI Key | MFYSYFVPBJMHGN-ZPOLXVRWSA-N |
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| Chemical Taxonomy |
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| Description | 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Steroids and steroid derivatives |
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| Sub Class | Hydroxysteroids |
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| Direct Parent | 21-hydroxysteroids |
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| Alternative Parents | |
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| Substituents | - Progestogin-skeleton
- 21-hydroxysteroid
- Pregnane-skeleton
- 20-oxosteroid
- 3-oxo-delta-4-steroid
- 3-oxosteroid
- 17-hydroxysteroid
- Oxosteroid
- 11-oxosteroid
- Delta-4-steroid
- Cyclohexenone
- Alpha-hydroxy ketone
- Cyclic alcohol
- Tertiary alcohol
- Cyclic ketone
- Ketone
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Primary alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Expected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cell membrane
- Cytoplasm
- Endoplasmic reticulum
- Membrane
- Myelin sheath
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 222 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.28 mg/mL at 25 °C | Not Available | | LogP | 1.47 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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