Deoxycorticosterone (CHEM003205)

Record Information
Version1.0
Creation Date2014-08-29 06:02:24 UTC
Update Date2026-04-14 20:31:53 UTC
Accession NumberCHEM003205
Identification
Common NameDeoxycorticosterone
ClassSmall Molecule
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 . Deoxycorticosterone can be used to treat adrenal insufficiency. In particular, desoxycorticosterone acetate (DOCA) is used as replacement therapy in Addison's disease.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Animal Toxin
  • Ester
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
21-Hydroxy-4-pregnene-3,20-dioneChEBI
21-HydroxyprogesteroneChEBI
4-Pregnen-21-ol-3,20-dioneChEBI
CortexoneChEBI
DESOXYCORTICOSTERONEChEBI
DesoxycortoneChEBI
DOCChEBI
Kendall's desoxy compound bChEBI
Reichstein's substance QChEBI
11-DehydroxycorticosteroneHMDB
11-Deoxy-corticosteroneHMDB
11-DeoxycorticosteroneHMDB
11-DesoxycorticosteroneHMDB
21-Hydroxy-3,20-dioxopregn-4-eneHMDB
21-Hydroxy-D4-pregnane-3,20-dioneHMDB
21-Hydroxy-D4-pregnene-3,20-dioneHMDB
21-Hydroxy-pregn-4-ene-3,20-dioneHMDB
21-Hydroxy-progesteroneHMDB
21-Hydroxypregn-4-ene-3,20-dioneHMDB
D4-Pregnene-21-ol-3,20-dioneHMDB
DeoxycortoneHMDB
DocaHMDB
11-DecorticosteroneHMDB
21 HydroxyprogesteroneHMDB
11 DecorticosteroneHMDB
21 Hydroxy 4 pregnene 3,20 dioneHMDB
DeoxycorticosteroneChEBI
Chemical FormulaC21H30O3
Average Molecular Mass330.461 g/mol
Monoisotopic Mass330.219 g/mol
CAS Registry Number64-85-7
IUPAC Name(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
SMILES[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI IdentifierInChI=1S/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
InChI KeyZESRJSPZRDMNHY-YFWFAHHUSA-N
Chemical Taxonomy
Description 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
Substituents
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • Pregnane-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue Locations
  • All Tissues
Pathways
NameSMPDB LinkKEGG Link
SteroidogenesisSMP00130 map00140
17-alpha-hydroxylase deficiency (CYP17)SMP00566 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point141 - 142°C
Boiling PointNot Available
Solubility0.0595 mg/mL at 37°C
Predicted Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP3.1ALOGPS
logP3.33ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.41 m³·mol⁻¹ChemAxon
Polarizability38.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsChronically high levels of deoxycorticosterone are associated with the inborn errors of metabolism known as Congenital adrenal hyperplasia.
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0000016
FooDB IDFDB006404
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID41397
BioCyc ID11-DEOXYCORTICOSTERONE
METLIN ID5089
PDB IDNot Available
Wikipedia LinkDesoxycorticosterone
Chemspider ID5932
ChEBI ID16973
PubChem Compound ID6166
Kegg Compound IDC03205
YMDB IDNot Available
ECMDB IDM2MDB005074
References
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.
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
2. 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.
3. 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.
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.
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.
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.
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.
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.
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.
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.
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.
12. Deng PY, Li YJ: Calcitonin gene-related peptide and hypertension. Peptides. 2005 Sep;26(9):1676-85. Epub 2005 Mar 2.
13. Funder JW: Mineralocorticoid receptors: distribution and activation. Heart Fail Rev. 2005 Jan;10(1):15-22.
14. Bassett MH, White PC, Rainey WE: The regulation of aldosterone synthase expression. Mol Cell Endocrinol. 2004 Mar 31;217(1-2):67-74.
15. White PC, Tusie-Luna MT, New MI, Speiser PW: Mutations in steroid 21-hydroxylase (CYP21). Hum Mutat. 1994;3(4):373-8.
16. 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.
17. 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.
18. Azar ST, Melby JC: 19-Nor-deoxycorticosterone production from aldosterone-producing adenomas. Hypertension. 1992 Apr;19(4):362-4.
19. 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.
20. Mellon SH, Miller WL: Extraadrenal steroid 21-hydroxylation is not mediated by P450c21. J Clin Invest. 1989 Nov;84(5):1497-502.
21. Hogan MJ, Schambelan M, Biglieri EG: Concurrent hypercortisolism and hypermineralocorticoidism. Am J Med. 1977 May;62(5):777-82.
22. 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.
23. 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.
24. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
25. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
26. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
27. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
28. Gupta S, Melendez J, Khanna A: Deoxycorticosterone producing tumor as a cause of resistant hypertension. Case Rep Med. 2010;2010:372719. doi: 10.1155/2010/372719. Epub 2010 Jun 30.
29. The lipid handbook with CD-ROM