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Bovine Metabolome Database



Showing metabocard for Cortexolone (BMDB00015)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:37
Accession Number BMDB00015
Common Name Cortexolone
Description Cortexolone is the precursor of cortisol. Accumulation of Cortexolone can happen in a defect known as congenital adrenal hyperplasia, which is due to 11-beta-hydroxylase deficiency, resulting in androgen excess, virilization, and hypertension. (PMID: 2022736) A 17-hydroxycorticosteroid with glucocorticoid and anti-inflammatory activities. (PubChem)
Synonyms
  1. 11-Deoxy-17-hydroxycorticosterone
  2. 11-Deoxycortisol
  3. 11-Deoxyhydrocortisone
  4. 11-Desoxy-17-hydroxycorticosterone
  5. 11-Desoxycortisol
  6. 11-Desoxyhydrocortisone
  7. 11-Dioxycortisol
  8. 11-deoxy-17-hydroxy-Corticosterone
  9. 11-deoxy-Cortisol
  10. 11-dioxy-Cortisol
  11. 17,21-Dihydroxy-4-pregnene-3,20-dione
  12. 17,21-Dihydroxyprogesterone
  13. 17,21-dihydroxypregn-4-ene-3,20-dione
  14. 17-Hydroxy-11-deoxycorticosterone
  15. 17alpha-Hydroxycortexone
  16. 20-dione 17,21-Dihydroxypregn-4-ene-3
  17. 4-Pregnene-17alpha,21-diol-3,20-dione
  18. Cortodoxone
  19. Reichstein S
  20. Reichstein's compound S
  21. Reichstein's substance S
Chemical IUPAC Name 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
Chemical Formula C21H30O4
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; tertiary alcohol; alkene
Biofunction
  • Hormones, Membrane component
Application
Source
  • Endogenous
Average Molecular Weight 346.461
Monoisotopic Molecular Weight 346.214417
Isomeric SMILES C[C@]12CCC(=O)C=C1CC[C@@H]1C2CC[C@@]2(C)C1CC[C@]2(O)C(=O)CO
Canonical SMILES CC12CCC(=O)C=C1CCC1C2CCC2(C)C1CCC2(O)C(=O)CO
KEGG Compound ID C05488 Link Image
BioCyc ID 11-DEOXY-CORTISOL Link Image
BiGG ID 45914 Link Image
Wikipedia Link Cortexolone Link Image
METLIN ID 5088 Link Image
PubChem Compound 440707 Link Image
PubChem Substance 3135470 Link Image
ChEBI ID Not Available
CAS Registry Number 152-58-9
InChI Identifier InChI=1/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17?,19+,20+,21+/m1/s1
Synthesis Reference Luu, Duc Huy. New method for the synthesis of Reichstein's compound S from pregnene. Tap Chi Duoc Hoc (2002), (9), 23-25.
Melting Point (Experimental) 215 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.0152 mg/mL [MEYLAN,WM et al. (1996)]; 0.025 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity 3.08 [SANGSTER (1994)] Source: PhysProp
Predicted LogP/Hydrophobicity 2.79 [Predicted by ALOGPS]; 2.4 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
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 (Predicted from LogP)
  • Cytoplasm (Predicted from Solubility)
  • 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
Image Show Link Image
KEGG Pathways
Name C21 Steroid Hormone Metabolism
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SimCell Pathways
Name C21 Steroid Hormone Metabolism
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Graph
SBML
General References
  1. Wikipedia Link Image