| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 11-Dehydroxycorticosterone
- 11-Deoxy-Corticosterone
- 11-Deoxycorticosterone
- 11-Desoxycorticosterone
- 21-Hydroxy-3,20-dioxopregn-4-ene
- 21-Hydroxy-D4-pregnane-3,20-dione
- 21-Hydroxy-D4-pregnene-3,20-dione
- 21-Hydroxy-Pregn-4-ene-3,20-dione
- 21-Hydroxy-Progesterone
- 21-Hydroxypregn-4-ene-3,20-dione
- 21-Hydroxyprogesterone
- 4-Pregnen-21-ol-3,20-dione
- Cortexone
- D4-Pregnene-21-ol-3,20-dione
- Deoxycortone
- Desoxycorticosterone
- Desoxycortone
- DOC
- Doca
- Kendall'S desoxy compound B
- 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 |
|
| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Hormones, Membrane component
- Membrane integrity/stability
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| 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 |
|
| Spectra |
|---|
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| Biological Properties |
|---|
| Cellular Locations |
- Cytoplasm
- Extracellular
- Membrane
- Mitochondria
- Endoplasmic reticulum
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| Biofluid Locations |
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| Tissue Location |
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| Pathways |
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| Normal Concentrations |
|---|
|
| 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 |
| External Links |
|---|
| 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  |
| KEGG Compound ID |
C03205 |
| BioCyc ID |
11-DEOXYCORTICOSTERONE |
| BiGG ID |
41397 |
| Wikipedia Link |
Deoxycorticosterone |
| NuGOwiki Link |
HMDB00016 |
| Metagene Link |
HMDB00016 |
| METLIN ID |
5089 |
| PubChem Compound |
6166 |
| PDB ID |
1CA |
| ChEBI ID |
16973 |
| 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 |
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Deng PY, Li YJ: Calcitonin gene-related peptide and hypertension. Peptides. 2005 Sep;26(9):1676-85. Epub 2005 Mar 2.
Pubmed: 16112410
- Funder JW: Mineralocorticoid receptors: distribution and activation. Heart Fail Rev. 2005 Jan;10(1):15-22.
Pubmed: 15947887
- 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
- White PC, Tusie-Luna MT, New MI, Speiser PW: Mutations in steroid 21-hydroxylase (CYP21). Hum Mutat. 1994;3(4):373-8.
Pubmed: 8081391
- 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
- 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
- Azar ST, Melby JC: 19-Nor-deoxycorticosterone production from aldosterone-producing adenomas. Hypertension. 1992 Apr;19(4):362-4.
Pubmed: 1555868
- 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
- Mellon SH, Miller WL: Extraadrenal steroid 21-hydroxylation is not mediated by P450c21. J Clin Invest. 1989 Nov;84(5):1497-502.
Pubmed: 2808702
- Hogan MJ, Schambelan M, Biglieri EG: Concurrent hypercortisolism and hypermineralocorticoidism. Am J Med. 1977 May;62(5):777-82.
Pubmed: 871129
- 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
- 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
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