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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-13 02:06:56 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[²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name11-deoxycorticosterone
CAS Registry Number64-85-7
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 20-oxosteroid
  • Oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 Solubility0.017 mg/mLALOGPS
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
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)splash10-lz61100000-c5e47cf4a734228e8190View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-210z000000-e7a6d422ea2bacd462a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-vz00000000-2a8ec06e636135e7f1a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-zk00000000-5f9c88fc7ed062bfa3f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-zpg2000000-3a4ef053cdcc6d13ad03View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-2gz4000000-8f8a662c709ceb10d5a1View in MoNA
MSMass Spectrum (Electron Ionization)splash10-ozs4000000-e4a2b497c3f190237679View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Endoplasmic reticulum
Biofluid Locations
  • Amniotic Fluid
  • Blood
Tissue Location
  • All Tissues
11-beta-hydroxylase deficiency (CYP11B1)SMP00575Not Available
17-alpha-hydroxylase deficiency (CYP17)SMP00566Not Available
21-hydroxylase deficiency (CYP21)SMP00576Not Available
3-Beta-Hydroxysteroid Dehydrogenase DeficiencySMP00718Not Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase DeficiencySMP00373Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase DeficiencySMP00372Not Available
Apparent mineralocorticoid excess syndromeSMP00717Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAHSMP00371Not Available
Corticosterone methyl oxidase I deficiency (CMO I)SMP00577Not Available
Corticosterone methyl oxidase II deficiency - CMO IISMP00578Not Available
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. [8081391 ]
  2. Mellon SH, Miller WL: Extraadrenal steroid 21-hydroxylation is not mediated by P450c21. J Clin Invest. 1989 Nov;84(5):1497-502. [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. [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. [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. [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. [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. [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. [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. [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. [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. [15483094 ]
  12. Deng PY, Li YJ: Calcitonin gene-related peptide and hypertension. Peptides. 2005 Sep;26(9):1676-85. Epub 2005 Mar 2. [16112410 ]
  13. Funder JW: Mineralocorticoid receptors: distribution and activation. Heart Fail Rev. 2005 Jan;10(1):15-22. [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. [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. [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. [15816373 ]
  17. Azar ST, Melby JC: 19-Nor-deoxycorticosterone production from aldosterone-producing adenomas. Hypertension. 1992 Apr;19(4):362-4. [1555868 ]
  18. Hogan MJ, Schambelan M, Biglieri EG: Concurrent hypercortisolism and hypermineralocorticoidism. Am J Med. 1977 May;62(5):777-82. [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. [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. [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. [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