11-Deoxycortisol (BioCAD00000001774)
Metabolite Card
Chinese Name: 11-去氧皮质醇
Formula: C21H30O4 (346.2144)
SMILES:
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Synonyms [en]
Cortodoxone; 11-Deoxycortisol; Reichstein's substance S; Cortexolone; 17,21-Dihydroxypregn-4-ene-3,20-dione; 11-Deoxyhydrocortisone
Last reviewed on 2026-04-16.
Cite this Page
11-Deoxycortisol. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/11-Deoxycortisol
(retrieved
2026-08-20) (CAD Registry RN: BioCAD00000001774). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
Cortexolone, also known as cortodoxone or 11-deoxycortisol, 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, cortexolone is considered to be a steroid molecule. Cortexolone is an endogenous glucocorticoid steroid hormone, and a metabolic intermediate in the synthesis of cortisol. It was first described by Tadeusz Reichstein in 1938 and named as Substance S. It has also been referred to as Reichstein's Substance S or Compound S. Cortexolone acts as a glucocorticoid, though it is less potent than cortisol. Cortexolone is synthesized from 17α-hydroxyprogesterone by 21-hydroxylase and is converted to cortisol by 11β-hydroxylase. As a result, the level of cortexolone is often measured in patients to diagnose impaired cortisol synthesis, to identify any enzyme deficiency that may be causing impairment along the pathway to cortisol, and to differentiate adrenal disorders. Cortexolone in mammals has limited biological activity and mainly acts as metabolic intermediate within the glucocorticoid pathway, leading to cortisol. On the other hand, in sea lampreys, cortexolone is the major glucocorticoid, with mineralocorticoid activity. Cortexolone in sea lampreys binds to specific corticosteroid receptors and is involved in intestinal osmoregulation and in sea lamprey at metamorphosis, a process in which they develop seawater tolerance before downstream migration.
DBLinks
- CAS Registry Number: 152-58-9
- PubChem CID: 440707
- ChEBI: 181455
- HMDB: HMDB0000015
- LipidMaps: LMST02030086
- KEGG: C05488
- BioCyc: 11-DEOXY-CORTISOL
- NCBI MeSH: Cortodoxone
- Wikipedia: Cortexolone
Other DBLinks
- CAS Registry Number: 152-58-9
- CAS Registry Number: 599-14-4
- PubChem: 440707
- ChEBI: ChEBI:181455
- ChEBI: ChEBI:28324
- HMDB: HMDB0000015
- LipidMaps: LMST02030086
- KEGG: C05488
- BioCyc: 11-DEOXY-CORTISOL
- NCBI MeSH: Cortodoxone
- Wikipedia: 11-Deoxycortisol
- Wikipedia: Cortexolone
- RefMet: RM0135768
- MoNA: CCMSLIB00005463873
- MoNA: CCMSLIB00005463874
- MoNA: FiehnHILIC000278
- MoNA: FiehnHILIC001131
- MoNA: FiehnHILIC001851
- MoNA: FiehnHILIC002442
- MoNA: MoNA034646
- MoNA: MoNA034648
- MoNA: MoNA034650
- MoNA: MoNA036374
- MoNA: MoNA036375
- MoNA: MoNA036378
- MoNA: MoNA037341
- MoNA: MoNA038090
- MoNA: MoNA038681
- MoNA: VF-NPL-LTQ000119
- MoNA: VF-NPL-LTQ000120
- MoNA: VF-NPL-QEHF000283
- MoNA: VF-NPL-QEHF000284
- MoNA: VF-NPL-QEHF000285
- MoNA: VF-NPL-QEHF000286
- MoNA: VF-NPL-QEHF000287
- MoNA: VF-NPL-QEHF000288
- MoNA: VF-NPL-QTOF007159
- MoNA: VF-NPL-QTOF007160
- MoNA: VF-NPL-QTOF007161
- MoNA: VF-NPL-QTOF007162
- MoNA: VF-NPL-QTOF007163
- MoNA: VF-NPL-QTOF007164
- Coconut NaturalProduct: CNP0130973.2
- Coconut NaturalProduct: CNP0130973.6
- Coconut NaturalProduct: CNP0312178.1
- Coconut NaturalProduct: CNP0481131.1
- Coconut NaturalProduct: CNP0504132.1
- metaboanalyst: 6c243a144b00405fc66c1350b4ecd7ef
- HERB: HBIN002048
Class / Ontology
- WishartLab ClassyFire: [Hydroxysteroids] Hydroxysteroids
- RefMet: [C21 steroids] C21 steroids
- LipidMaps: [C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]] C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
- ChEBI: [CHEBI:28324] 11-deoxycortisol
- ChEBI: [CHEBI:181455] (8R,10R,13S,17R)-17-Hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
- Coconut NaturalProduct: [Pregnane steroids] Pregnane steroids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R02843 | 1.14.15.4 | steroid,reduced ferredoxin:oxygen oxidoreductase (11-hydroxylating) |
| KEGG:R03326 | 1.14.14.16 | 17alpha-hydroxyprogesterone,NADPH-hemoprotein reductase:oxygen oxidoreductase (21-hydroxylating) |
| KEGG:R04849 | 1.1.1.145 | 11-deoxycortisol delta5-delat4-isomerase; |
| Rhea:RHEA:46101 | 11-deoxycortisol + 2 reduced [adrenodoxin] + O2 + 2 H+ => cortisol + 2 oxidized [adrenodoxin] + H2O | |
| Rhea:RHEA:46102 | cortisol + 2 oxidized [adrenodoxin] + H2O => 11-deoxycortisol + 2 reduced [adrenodoxin] + O2 + 2 H+ | |
| Rhea:RHEA:46103 | 11-deoxycortisol + 2 reduced [adrenodoxin] + O2 + 2 H+ <=> cortisol + 2 oxidized [adrenodoxin] + H2O | |
| Rhea:RHEA:50309 | 1.14.14.16 | 17α-hydroxyprogesterone + reduced [NADPH—hemoprotein reductase] + O2 => 11-deoxycortisol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ |
| Rhea:RHEA:50310 | 1.14.14.16 | 11-deoxycortisol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => 17α-hydroxyprogesterone + reduced [NADPH—hemoprotein reductase] + O2 |
| Rhea:RHEA:50311 | 1.14.14.16 | 17α-hydroxyprogesterone + reduced [NADPH—hemoprotein reductase] + O2 <=> 11-deoxycortisol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ |
| Rhea:RHEA:76164 | 11-deoxycortisol + 2 reduced [adrenodoxin] + O2 + 2 H+ => 18-hydroxy-11-deoxycortisol + 2 oxidized [adrenodoxin] + H2O | |
| Rhea:RHEA:76165 | 18-hydroxy-11-deoxycortisol + 2 oxidized [adrenodoxin] + H2O => 11-deoxycortisol + 2 reduced [adrenodoxin] + O2 + 2 H+ | |
| Rhea:RHEA:76166 | 11-deoxycortisol + 2 reduced [adrenodoxin] + O2 + 2 H+ <=> 18-hydroxy-11-deoxycortisol + 2 oxidized [adrenodoxin] + H2O | |
| BioCyc:RXN66-357 | 1.14.15.4 | 11-DEOXY-CORTISOL + 2 Reduced-adrenal-ferredoxins + OXYGEN-MOLECULE + 2 PROTON --> WATER + CORTISOL + 2 Oxidized-adrenal-ferredoxins |
| BioCyc:TRANS-RXN-420 | 11-DEOXY-CORTISOL --> 11-DEOXY-CORTISOL | |
| BioCyc:RXN66-356 | 1.14.14.16 | 17-ALPHA-HYDROXYPROGESTERONE + Red-NADPH-Hemoprotein-Reductases + OXYGEN-MOLECULE --> 11-DEOXY-CORTISOL + Ox-NADPH-Hemoprotein-Reductases + WATER |
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| Reactome:R-BTA-1430728 | Metabolism |
| Reactome:R-BTA-556833 | Metabolism of lipids |
| Reactome:R-BTA-194002 | Glucocorticoid biosynthesis |
| Reactome:R-BTA-211945 | Phase I - Functionalization of compounds |
| Reactome:R-CFA-1430728 | Metabolism |
| Reactome:R-CFA-556833 | Metabolism of lipids |
| Reactome:R-CFA-194002 | Glucocorticoid biosynthesis |
| Reactome:R-CFA-211976 | Endogenous sterols |
| Reactome:R-DRE-196071 | Metabolism of steroid hormones |
| Reactome:R-GGA-194002 | Glucocorticoid biosynthesis |
| Reactome:R-HSA-194002 | Glucocorticoid biosynthesis |
| Reactome:R-HSA-211859 | Biological oxidations |
| Reactome:R-HSA-1643685 | Disease |
| Reactome:R-MMU-1430728 | Metabolism |
| Reactome:R-MMU-556833 | Metabolism of lipids |
| Reactome:R-MMU-8957322 | Metabolism of steroids |
| Reactome:R-MMU-211859 | Biological oxidations |
| Reactome:R-RNO-196071 | Metabolism of steroid hormones |
| Reactome:R-RNO-211945 | Phase I - Functionalization of compounds |
| Reactome:R-SSC-196071 | Metabolism of steroid hormones |