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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-13 23:03:49 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameDeoxycorticosterone
DescriptionDeoxycorticosterone 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.
  1. 11-Dehydroxycorticosterone
  2. 11-Deoxy-Corticosterone
  3. 11-Deoxycorticosterone
  4. 11-Desoxycorticosterone
  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-Hydroxy-Pregn-4-ene-3,20-dione
  9. 21-Hydroxy-Progesterone
  10. 21-Hydroxypregn-4-ene-3,20-dione
  11. 21-Hydroxyprogesterone
  12. 4-Pregnen-21-ol-3,20-dione
  13. Cortexone
  14. D4-Pregnene-21-ol-3,20-dione
  15. Deoxycortone
  16. Desoxycorticosterone
  17. Desoxycortone
  18. DOC
  19. Doca
  20. Kendall'S desoxy compound B
  21. Reichstein'S substance Q
Chemical FormulaC21H30O3
Average Molecular Weight330.4611
Monoisotopic Molecular Weight330.219494826
IUPAC Name(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name11-deoxycorticosterone
CAS Registry Number64-85-7
InChI Identifier
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassGluco/mineralocorticoids, Progestogins and Derivatives
Other Descriptors
  • 20-oxo steroid(ChEBI)
  • 21-hydroxy steroid(ChEBI)
  • 3-oxo Delta(4)-steroid(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives(KEGG)
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives(Lipidmaps)
  • Mineralocorticoids(KEGG)
  • Pregnane and derivatives [Fig](KEGG)
  • mineralocorticoid(ChEBI)
  • 20 Keto Steroid
  • 3 Keto Steroid
  • Alpha Ketoaldehyde
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
  • Primary Alcohol
Direct ParentGluco/mineralocorticoids, Progestogins and Derivatives
StatusDetected and Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Endoplasmic reticulum
Physical Properties
Experimental Properties
Melting Point141 - 142 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0595 mg/mL at 37 °CNot Available
LogP2.88HANSCH,C ET AL. (1995)
Predicted Properties
Water Solubility0.017ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.41 m3·mol-1ChemAxon
Polarizability38.19 Å3ChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Endoplasmic reticulum
Biofluid Locations
  • Amniotic Fluid
  • Blood
Tissue Location
  • All Tissues
Normal Concentrations
Amniotic FluidDetected and Quantified10.591 +/- 1.997 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.073 (0.034-0.11) uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021873
KNApSAcK IDNot Available
Chemspider ID5932
KEGG Compound IDC03205
BiGG ID41397
Wikipedia LinkDeoxycorticosterone
NuGOwiki LinkHMDB00016
Metagene LinkHMDB00016
PubChem Compound6166
ChEBI ID16973
Synthesis ReferenceMattox V R; Goodrich J E; Vrieze W D Synthesis of C-21 glucosiduronates of cortisone and related corticosteroids. Biochemistry (1969), 8(3), 1188-99.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. White PC, Tusie-Luna MT, New MI, Speiser PW: Mutations in steroid 21-hydroxylase (CYP21). Hum Mutat. 1994;3(4):373-8. Pubmed: 8081391
  2. Mellon SH, Miller WL: Extraadrenal steroid 21-hydroxylation is not mediated by P450c21. J Clin Invest. 1989 Nov;84(5):1497-502. Pubmed: 2808702
  3. 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
  4. Muto S, Akai Y, Ono S, Kusano E, Asano Y: Selective hypoaldosteronism due to combined defects of the conversion from inactive renin to active renin and the aldosterone biosynthesis from corticosterone. Nephron. 2001 Jul;88(3):247-53. Pubmed: 11423756
  5. Bruynseels J, De Coster R, Van Rooy P, Wouters W, Coene MC, Snoeck E, Raeymaekers A, Freyne E, Sanz G, Vanden Bussche G, et al.: R 75251, a new inhibitor of steroid biosynthesis. Prostate. 1990;16(4):345-57. Pubmed: 2164659
  6. Holmes NM, Miller WL, Baskin LS: Lack of defects in androgen production in children with hypospadias. J Clin Endocrinol Metab. 2004 Jun;89(6):2811-6. Pubmed: 15181062
  7. Sippell WG, Muller-Holve W, Dorr HG, Bidlingmaier F, Knorr D: Concentrations of aldosterone, corticosterone, 11-deoxycorticosterone, progesterone, 17-hydroxyprogesterone, 11-deoxycortisol, cortisol, and cortisone determined simultaneously in human amniotic fluid throughout gestation. J Clin Endocrinol Metab. 1981 Mar;52(3):385-92. Pubmed: 7462398
  8. Namiki M, Koh E, Meguro N, Kondoh N, Kiyohara H, Okuyama A, Sakoda S, Matsumoto K, Sonoda T: Extraadrenal expression of steroid 21-hydroxylase and 11 beta-hydroxylase by a benign testicular Leydig cell tumor. J Steroid Biochem Mol Biol. 1991 Dec;39(6):897-901. Pubmed: 1751389
  9. Wyss JM, Oparil S, Sripairojthikoon W: Neuronal control of the kidney: contribution to hypertension. Can J Physiol Pharmacol. 1992 May;70(5):759-70. Pubmed: 1423019
  10. Pakravan P, Kenny FM, Depp R, Allen AC: Familial congenital absence of adrenal glands; evaluation of glucocorticoid, mineralocorticoid, and estrogen metabolism in the perinatal period. J Pediatr. 1974 Jan;84(1):74-8. Pubmed: 12119960
  11. Krone N, Riepe FG, Grotzinger J, Partsch CJ, Sippell WG: Functional characterization of two novel point mutations in the CYP21 gene causing simple virilizing forms of congenital adrenal hyperplasia due to 21-hydroxylase deficiency. J Clin Endocrinol Metab. 2005 Jan;90(1):445-54. Epub 2004 Oct 13. Pubmed: 15483094
  12. Deng PY, Li YJ: Calcitonin gene-related peptide and hypertension. Peptides. 2005 Sep;26(9):1676-85. Epub 2005 Mar 2. Pubmed: 16112410
  13. Funder JW: Mineralocorticoid receptors: distribution and activation. Heart Fail Rev. 2005 Jan;10(1):15-22. Pubmed: 15947887
  14. Bassett MH, White PC, Rainey WE: The regulation of aldosterone synthase expression. Mol Cell Endocrinol. 2004 Mar 31;217(1-2):67-74. Pubmed: 15134803
  15. Ahmad N, Romero DG, Gomez-Sanchez EP, Gomez-Sanchez CE: Do human vascular endothelial cells produce aldosterone? Endocrinology. 2004 Aug;145(8):3626-9. Epub 2004 Apr 29. Pubmed: 15117882
  16. Mussig K, Wehrmann M, Horger M, Maser-Gluth C, Haring HU, Overkamp D: Adrenocortical carcinoma producing 11-deoxycorticosterone: a rare cause of mineralocorticoid hypertension. J Endocrinol Invest. 2005 Jan;28(1):61-5. Pubmed: 15816373
  17. Azar ST, Melby JC: 19-Nor-deoxycorticosterone production from aldosterone-producing adenomas. Hypertension. 1992 Apr;19(4):362-4. Pubmed: 1555868
  18. Hogan MJ, Schambelan M, Biglieri EG: Concurrent hypercortisolism and hypermineralocorticoidism. Am J Med. 1977 May;62(5):777-82. Pubmed: 871129
  19. Ni W, Thompson JM, Northcott CA, Lookingland K, Watts SW: The serotonin transporter is present and functional in peripheral arterial smooth muscle. J Cardiovasc Pharmacol. 2004 Jun;43(6):770-81. Pubmed: 15167270
  20. Campion J, Lahera V, Cachofeiro V, Maestro B, Davila N, Carranza MC, Calle C: In vivo tissue specific modulation of rat insulin receptor gene expression in an experimental model of mineralocorticoid excess. Mol Cell Biochem. 1998 Aug;185(1-2):177-82. Pubmed: 9746224


General function:
Involved in monooxygenase activity
Specific function:
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:
Uniprot ID:
Molecular weight:
Deoxycorticosterone + Reduced ferredoxin + Oxygen → Corticosterone + Oxidized ferredoxin + Waterdetails
Deoxycorticosterone + Reduced adrenal ferredoxin + Oxygen → Aldosterone + Oxidized adrenal ferredoxin + Waterdetails
  1. 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
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates target genes. The effect of MC is to increase ion and water transport and thus raise extracellular fluid volume and blood pressure and lower potassium levels
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
Gene Name:
Uniprot ID:
Molecular weight:
21-Hydroxypregnenolone + NAD → Deoxycorticosterone + NADH + Hydrogen Iondetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:
Uniprot ID:
Molecular weight:
21-Hydroxypregnenolone + NAD → Deoxycorticosterone + NADH + Hydrogen Iondetails
General function:
Involved in monooxygenase activity
Specific function:
Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name:
Uniprot ID:
Molecular weight:
Deoxycorticosterone + Reduced ferredoxin + Oxygen → Corticosterone + Oxidized ferredoxin + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Not Available
Specific function:
Specifically catalyzes the 21-hydroxylation of steroids. Required for the adrenal synthesis of mineralocorticoids and glucocorticoids.
Gene Name:
Uniprot ID:
Molecular weight:
Progesterone + Reduced acceptor + Oxygen → Deoxycorticosterone + Acceptor + Waterdetails