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Bovine Metabolome Database



Showing metabocard for Deoxycorticosterone (BMDB00016)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:38
Accession Number BMDB00016
Common Name Deoxycorticosterone
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 [Wikipedia]. Deoxycorticosterone can be used to treat adrenal insufficiency. In particular, desoxycorticosterone acetate (DOCA) is used as replacement therapy in Addison's disease.
Synonyms
  1. 11-Dehydroxycorticosterone
  2. 11-Deoxycorticosterone
  3. 11-Desoxycorticosterone
  4. 11-deoxy-Corticosterone
  5. 21-Hydroxy-3,20-dioxopregn-4-ene
  6. 21-Hydroxy-D4-pregnane-3,20-dione
  7. 21-Hydroxy-D4-pregnene-3,20-dione
  8. 21-Hydroxypregn-4-ene-3,20-dione
  9. 21-Hydroxyprogesterone
  10. 21-hydroxy-Pregn-4-ene-3,20-dione
  11. 21-hydroxy-Progesterone
  12. 4-Pregnen-21-ol-3,20-dione
  13. Cortexone
  14. D4-Pregnene-21-ol-3,20-dione
  15. DOC
  16. Deoxycortone
  17. Desoxycorticosterone
  18. Desoxycortone
  19. Doca
  20. Kendall's desoxy compound B
  21. Reichstein's substance Q
Chemical IUPAC Name 17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Chemical Formula C21H30O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Ketosteroids
Family
  • Mammalian_Metabolite
Species
  • ketone; primary alcohol; alkene
Biofunction
  • Hormones, Membrane component
Application
Source
  • Endogenous
Average Molecular Weight 330.461
Monoisotopic Molecular Weight 330.219482
Isomeric SMILES C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@H]2C(=O)CO
Canonical SMILES CC12CCC3C(CCC4=CC(=O)CCC34C)C1CCC2C(=O)CO
KEGG Compound ID C03205 Link Image
BioCyc ID 11-DEOXYCORTICOSTERONE Link Image
BiGG ID 41397 Link Image
Wikipedia Link Deoxycorticosterone Link Image
METLIN ID 5089 Link Image
PubChem Compound 6166 Link Image
PubChem Substance 11466985 Link Image
ChEBI ID 16973 Link Image
CAS Registry Number 64-85-7
InChI Identifier InChI=1/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
Synthesis Reference Mattox V R; Goodrich J E; Vrieze W D Synthesis of C-21 glucosiduronates of cortisone and related corticosteroids. Biochemistry (1969), 8(3), 1188-99.
Melting Point (Experimental) 141-142 oC
Experimental Water Solubility 0.0595 mg/mL at 37 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 0.0167 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity 2.88 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity 3.10 [Predicted by ALOGPS]; 2.5 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
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2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane
  • Cytoplasm
  • endoplasmic reticulum
  • mitochondria
Biofluid Location Not Available
Tissue Location
Tissue References
All Tissues
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • C21 Steroid Hormone Metabolism
HMDB Pathways
Name C21 Steroid Hormone Metabolism
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KEGG Pathways
Name C21 Steroid Hormone Metabolism
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SimCell Pathways
Name C21 Steroid Hormone Metabolism
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General References
  1. Wikipedia Link Image