Human Metabolome Database Version 3.5

Showing metabocard for Deoxycorticosterone (HMDB00016)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-13 17:03:49 -0600
HMDB ID HMDB00016
Secondary Accession Numbers None
Metabolite Identification
Common Name Deoxycorticosterone
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 (Wikipedia). Deoxycorticosterone can be used to treat adrenal insufficiency. In particular, desoxycorticosterone acetate (DOCA) is used as replacement therapy in Addison's disease.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  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 Formula C21H30O3
Average Molecular Weight 330.4611
Monoisotopic Molecular Weight 330.219494826
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 IUPAC Name 11-deoxycorticosterone
CAS Registry Number 64-85-7
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 Identifier InChI=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 Key ZESRJSPZRDMNHY-YFWFAHHUSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Gluco/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)
Substituents
  • 20 Keto Steroid
  • 3 Keto Steroid
  • Alpha Ketoaldehyde
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
  • Primary 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
  • Mitochondria
  • Endoplasmic reticulum
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 141 - 142 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.0595 mg/mL at 37 °C Not Available
LogP 2.88 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.017 g/L ALOGPS
LogP 3.10 ALOGPS
LogP 3.33 ChemAxon
LogS -4.30 ALOGPS
pKa (strongest acidic) 13.86 ChemAxon
pKa (strongest basic) -3.3 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 54.37 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 94.41 ChemAxon
Polarizability 38.19 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI M-80)
MS/MS Spectrum EI-B (HITACHI M-80)
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Endoplasmic reticulum
Biofluid Locations
  • Amniotic Fluid
  • Blood
Tissue Location
  • All Tissues
Pathways
Name SMPDB Link KEGG Link
Steroidogenesis SMP00130 map00140 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Amniotic Fluid Detected and Quantified
10.591 +/- 1.997 uM Adult (>18 years old) Female Normal
Blood Detected and Quantified
0.073 (0.034-0.11) uM 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 FDB021873
KNApSAcK ID Not Available
Chemspider ID 5932 Link_out
KEGG Compound ID C03205 Link_out
BioCyc ID 11-DEOXYCORTICOSTERONE Link_out
BiGG ID 41397 Link_out
Wikipedia Link Deoxycorticosterone Link_out
NuGOwiki Link HMDB00016 Link_out
Metagene Link HMDB00016 Link_out
METLIN ID 5089 Link_out
PubChem Compound 6166 Link_out
PDB ID 1CA Link_out
ChEBI ID 16973 Link_out
References
Synthesis Reference 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.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. Deng PY, Li YJ: Calcitonin gene-related peptide and hypertension. Peptides. 2005 Sep;26(9):1676-85. Epub 2005 Mar 2. Pubmed: 16112410 Link_out
  10. Funder JW: Mineralocorticoid receptors: distribution and activation. Heart Fail Rev. 2005 Jan;10(1):15-22. Pubmed: 15947887 Link_out
  11. 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 Link_out
  12. 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
  13. 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 Link_out
  14. 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 Link_out
  15. Azar ST, Melby JC: 19-Nor-deoxycorticosterone production from aldosterone-producing adenomas. Hypertension. 1992 Apr;19(4):362-4. Pubmed: 1555868 Link_out
  16. 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
  17. 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
  18. Hogan MJ, Schambelan M, Biglieri EG: Concurrent hypercortisolism and hypermineralocorticoidism. Am J Med. 1977 May;62(5):777-82. Pubmed: 871129 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Cytochrome P450 11B1, mitochondrial
Reactions:
Deoxycorticosterone + Reduced ferredoxin + Oxygen unknown Corticosterone + Oxidized ferredoxin + Water details
Deoxycorticosterone + Reduced adrenal ferredoxin + Oxygen unknown Aldosterone + Oxidized adrenal 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:
21-Hydroxypregnenolone + NAD unknown Deoxycorticosterone + NADH + Hydrogen Ion 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:
21-Hydroxypregnenolone + NAD unknown Deoxycorticosterone + NADH + Hydrogen Ion details
Gene Name: HSD3B2
Uniprot ID: P26439 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 11B2, mitochondrial
Reactions:
Deoxycorticosterone + Reduced ferredoxin + Oxygen unknown Corticosterone + 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:
Progesterone + Reduced acceptor + Oxygen unknown Deoxycorticosterone + Acceptor + Water details
Gene Name: CYP21A2
Uniprot ID: P08686 Link_out
Protein Sequence: FASTA