Human Metabolome Database Version 3.5

Showing metabocard for Cortexolone (HMDB00015)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:23:42 -0600
HMDB ID HMDB00015
Secondary Accession Numbers None
Metabolite Identification
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 Link_out) A 17-hydroxycorticosteroid with glucocorticoid and anti-inflammatory activities. (PubChem).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 11-Deoxy-17-hydroxy-Corticosterone
  2. 11-Deoxy-17-hydroxycorticosterone
  3. 11-Deoxy-Cortisol
  4. 11-Deoxycortisol
  5. 11-Deoxyhydrocortisone
  6. 11-Desoxy-17-hydroxycorticosterone
  7. 11-Desoxycortisol
  8. 11-Desoxyhydrocortisone
  9. 11-Dioxy-Cortisol
  10. 11-Dioxycortisol
  11. 17,21-Dihydroxy-4-pregnene-3,20-dione
  12. 17,21-Dihydroxypregn-4-ene-3,20-dione
  13. 17,21-Dihydroxyprogesterone
  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 Formula C21H30O4
Average Molecular Weight 346.4605
Monoisotopic Molecular Weight 346.214409448
IUPAC Name (2R,10R,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional IUPAC Name (2R,10R,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
CAS Registry Number 152-58-9
SMILES [H]C12CC[C@](O)(C(=O)CO)[C@@]1(C)CCC1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier InChI=1S/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
InChI Key WHBHBVVOGNECLV-HMGFGKNBSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Gluco/mineralocorticoids, Progestogins and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
Substituents
  • 17 Hydroxy Steroid
  • 20 Keto Steroid
  • 3 Keto Steroid
  • Alpha Ketoaldehyde
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
  • Primary Alcohol
  • Tertiary Alcohol
Direct Parent Gluco/mineralocorticoids, Progestogins and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Mitochondria
  • Endoplasmic reticulum
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 215 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 3.08 SANGSTER (1994)
Predicted Properties
Property Value Source
Water Solubility 0.025 g/L ALOGPS
LogP 2.79 ALOGPS
LogP 2.58 ChemAxon
LogS -4.14 ALOGPS
pKa (strongest acidic) 12.59 ChemAxon
pKa (strongest basic) -3.3 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 74.6 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 95.81 ChemAxon
Polarizability 38.78 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Mitochondria
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • All Tissues
Pathways
Name SMPDB Link KEGG Link
Steroidogenesis SMP00130 map00140 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.0039 +/- 0.0004 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.017-178.9 umol/mmol creatinine Newborn (0-30 days old) Both Normal
Urine Detected and Quantified
0.02 (0.0091-0.032) umol/mmol creatinine Adult (>18 years old) Female Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB021872
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C05488 Link_out
BioCyc ID 11-DEOXY-CORTISOL Link_out
BiGG ID 45914 Link_out
Wikipedia Link Cortexolone Link_out
NuGOwiki Link HMDB00015 Link_out
Metagene Link HMDB00015 Link_out
METLIN ID 5088 Link_out
PubChem Compound 53477676 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
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.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Homma K, Hasegawa T, Masumoto M, Takeshita E, Watanabe K, Chiba H, Kurosawa T, Takahashi T, Matsuo N: Reference values for urinary steroids in Japanese newborn infants: gas chromatography/mass spectrometry in selected ion monitoring. Endocr J. 2003 Dec;50(6):783-92. Pubmed: 14709852 Link_out
  2. Trakakis E, Laggas D, Salamalekis E, Creatsas G: 21-Hydroxylase deficiency: from molecular genetics to clinical presentation. J Endocrinol Invest. 2005 Feb;28(2):187-92. Pubmed: 15887869 Link_out
  3. Krone N, Riepe FG, Gotze D, Korsch E, Rister M, Commentz J, Partsch CJ, Grotzinger J, Peter M, Sippell WG: Congenital adrenal hyperplasia due to 11-hydroxylase deficiency: functional characterization of two novel point mutations and a three-base pair deletion in the CYP11B1 gene. J Clin Endocrinol Metab. 2005 Jun;90(6):3724-30. Epub 2005 Mar 8. Pubmed: 15755848 Link_out
  4. Adinoff B, Krebaum SR, Chandler PA, Ye W, Brown MB, Williams MJ: Dissection of hypothalamic-pituitary-adrenal axis pathology in 1-month-abstinent alcohol-dependent men, part 1: adrenocortical and pituitary glucocorticoid responsiveness. Alcohol Clin Exp Res. 2005 Apr;29(4):517-27. Pubmed: 15834216 Link_out
  5. Brown JR, Cavanaugh AH, Farnsworth WE: A simple radioimmunoassay for plasma cortisol and 11-deoxycortisol (17, 21-dihydroxy-4-pregnene-3, 20-dione). Steroids. 1976 Oct;28(4):487-98. Pubmed: 1034356 Link_out
  6. den Brinker M, Joosten KF, Liem O, de Jong FH, Hop WC, Hazelzet JA, van Dijk M, Hokken-Koelega AC: Adrenal insufficiency in meningococcal sepsis: bioavailable cortisol levels and impact of interleukin-6 levels and intubation with etomidate on adrenal function and mortality. J Clin Endocrinol Metab. 2005 Sep;90(9):5110-7. Epub 2005 Jun 28. Pubmed: 15985474 Link_out
  7. Lee HH, Won GS, Chao HT, Lee YJ, Chung BC: Novel missense mutations, GCC [Ala306]- > GTC [Val] and ACG [Thr318]- > CCG [Pro], in the CYP11B1 gene cause steroid 11beta-hydroxylase deficiency in the Chinese. Clin Endocrinol (Oxf). 2005 Apr;62(4):418-22. Pubmed: 15807871 Link_out
  8. Zachmann M, Tassinari D, Prader A: Clinical and biochemical variability of congenital adrenal hyperplasia due to 11 beta-hydroxylase deficiency. A study of 25 patients. J Clin Endocrinol Metab. 1983 Feb;56(2):222-9. Pubmed: 6296182 Link_out
  9. White PC, Tusie-Luna MT, New MI, Speiser PW: Mutations in steroid 21-hydroxylase (CYP21). Hum Mutat. 1994;3(4):373-8. Pubmed: 8081391 Link_out
  10. Bradshaw KD, Milewich L, Mason JI, Parker CR Jr, MacDonald PC, Carr BR: Steroid secretory characteristics of a virilizing adrenal adenoma in a woman. J Endocrinol. 1994 Feb;140(2):297-307. Pubmed: 8169562 Link_out
  11. Bureik M, Bruck N, Hubel K, Bernhardt R: The human mineralocorticoid receptor only partially differentiates between different ligands after expression in fission yeast. FEMS Yeast Res. 2005 Apr;5(6-7):627-33. Pubmed: 15780662 Link_out
  12. Dragan CA, Zearo S, Hannemann F, Bernhardt R, Bureik M: Efficient conversion of 11-deoxycortisol to cortisol (hydrocortisone) by recombinant fission yeast Schizosaccharomyces pombe. FEMS Yeast Res. 2005 Apr;5(6-7):621-5. Pubmed: 15780661 Link_out
  13. Mellon SH, Miller WL: Extraadrenal steroid 21-hydroxylation is not mediated by P450c21. J Clin Invest. 1989 Nov;84(5):1497-502. Pubmed: 2808702 Link_out
  14. Sakamoto N, Matsukura S, Tsuboi S, Tokumiya T, Imura H: Radioimmunoassay for 11-deoxycortisol using iodine-labeled tracer. Endocrinol Jpn. 1976 Aug;23(4):359-63. Pubmed: 1024042 Link_out
  15. Tjeerdsma G, Sluiter WJ, Hew JM, Molenaar WM, de Lange WE, Dullaart RP: Hyperprolactinaemia is associated with a higher prevalence of pituitary-adrenal dysfunction in non-functioning pituitary macroadenoma. Eur J Endocrinol. 1996 Sep;135(3):299-308. Pubmed: 8890720 Link_out
  16. Hughes IA, Arisaka O, Perry LA, Honour JW: Early diagnosis of 11 beta-hydroxylase deficiency in two siblings confirmed by analysis of a novel steroid metabolite in newborn urine. Acta Endocrinol (Copenh). 1986 Mar;111(3):349-54. Pubmed: 3515819 Link_out
  17. Curnow KM, Tusie-Luna MT, Pascoe L, Natarajan R, Gu JL, Nadler JL, White PC: The product of the CYP11B2 gene is required for aldosterone biosynthesis in the human adrenal cortex. Mol Endocrinol. 1991 Oct;5(10):1513-22. Pubmed: 1775135 Link_out
  18. White PC, Dupont J, New MI, Leiberman E, Hochberg Z, Rosler A: A mutation in CYP11B1 (Arg-448----His) associated with steroid 11 beta-hydroxylase deficiency in Jews of Moroccan origin. J Clin Invest. 1991 May;87(5):1664-7. Pubmed: 2022736 Link_out

Enzymes
Name: Cytochrome P450 11B1, mitochondrial
Reactions:
Cortexolone + Reduced ferredoxin + Oxygen unknown Hydrocortisone + Oxidized ferredoxin + Water details
Gene Name: CYP11B1
Uniprot ID: P15538 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Mineralocorticoid receptor
Reactions: Not Available
Gene Name: NR3C2
Uniprot ID: P08235 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1
Reactions:
Cortexolone + Hydrogen Ion + NADH unknown 17a,21-Dihydroxypreg-nenolone + NAD details
Gene Name: HSD3B1
Uniprot ID: P14060 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2
Reactions:
Cortexolone + Hydrogen Ion + NADH unknown 17a,21-Dihydroxypreg-nenolone + NAD details
Gene Name: HSD3B2
Uniprot ID: P26439 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 11B2, mitochondrial
Reactions:
Cortexolone + Reduced ferredoxin + Oxygen unknown Hydrocortisone + Oxidized ferredoxin + Water details
Gene Name: CYP11B2
Uniprot ID: P19099 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 21-hydroxylase
Reactions: Not Available
Gene Name: P450-CYP21B
Uniprot ID: Q16874 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450, family 21, subfamily A, polypeptide 2
Reactions: Not Available
Gene Name: CYP21A2
Uniprot ID: Q08AG9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Steroid 21-hydroxylase
Reactions:
17-Hydroxyprogesterone + Reduced acceptor + Oxygen unknown Cortexolone + Acceptor + Water details
Gene Name: CYP21A2
Uniprot ID: P08686 Link_out
Protein Sequence: FASTA