| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:07:52 -0700 |
| HMDB ID |
HMDB00077 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
Dehydroepiandrosterone |
| Description |
Dehydroepiandrosterone (DHEA) is a natural steroid hormone produced from cholesterol by the adrenal glands. DHEA is also produced in the gonads, adipose tissue and the brain. DHEA is structurally similar to, and is a precursor of, androstenedione, testosterone, estradiol, estrone and estrogen. It is the most abundant hormone in the human body. Most of DHEA is sulfated (dehydroepiandrosterone sulfate- DEHAS) before secretion. DHEAS is the sulfated version of DHEA; - this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEAS with levels that are about 300 times higher than free DHEA. Blood measurements of DHEAS/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have normal or mildly elevated levels of DHEAS. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- (+)-Dehydroisoandrosterone
- (3-beta)-3-Hydroxyandrost-5-en-17-one
- (3beta)-3-hydroxy-Androst-5-en-17-one
- (3beta,16alpha)-3,16-dihydroxy-androst-5-en-17-one
- 17-Chetovis
- 17-Hormoforin
- 3-beta-Hydroxy-5-androsten-17-one
- 3-beta-Hydroxyandrost-5-en-17-one
- 3b-Hydroxy-D5-androsten-17-one
- 3b-Hydroxyandrost-5-en-17-one
- 3beta-hydroxy-5-androsten-17-one
- 3beta-hydroxy-Androst-5-en-17-one
- 3beta-Hydroxy-D5-androsten-17-one
- 3beta-Hydroxyandrost-5-en-17-one
- 5,6-Dehydroisoandrosterone
- 5,6-Didehydroisoandrosterone
- 5-Androsten-3-beta-ol-17-one
- 5-Androsten-3b-ol-17-one
- 5-Androsten-3beta-ol-17-one
- 5-Dehydro-Epiandrosterone
- 5-Dehydroepiandrosterone
- Andrestenol
- Androst-5-ene-3b-ol-17-one
- Androst-5-ene-3beta-ol-17-one
- Androsten-3beta-ol-17-one
- Androstenolone
- Astenile
- D5-Androsten-3b-ol-17-one
- D5-Androsten-3beta-ol-17-one
- Deandros
- Dehydro-epi-androsterone
- Dehydroepiandrosterone
- Dehydroisoandrosterone
- Diandron
- Diandrone
- Hydroxyandrostenone
- Prasterona
- Prasterone
- Prasteronum
- Prestara
- Psicosterone
- trans-Dehydroandrosterone
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| Chemical Formula |
C19H28O2 |
| Average Molecular Weight |
288.4244 |
| Monoisotopic Molecular Weight |
288.20893014 |
| IUPAC Name |
(2R,5S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one |
| Traditional IUPAC Name |
(2R,5S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one |
| CAS Registry Number |
53-43-0 |
| SMILES |
C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CCC2=O |
| InChI Identifier |
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14?,15?,16?,18-,19-/m0/s1 |
| InChI Key |
FMGSKLZLMKYGDP-INNQQZFDSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Steroids and Steroid Derivatives |
| Sub Class |
Androgens and Derivatives |
| Other Descriptors |
- Aliphatic Homopolycyclic Compounds
- Hydroxysteroids
- a 3β-hydroxy-δ<sup>5</sup>-steroid(Cyc)
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| Substituents |
- Bicyclohexane
- Cyclic Alcohol
- Cyclohexane
- Cyclohexene
- Ketone
- Secondary Alcohol
- Sesquiterpene Backbone
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| Direct Parent |
Androgens and Derivatives |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
- Cell signaling
- Component of Androgen and estrogen metabolism
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
- Endoplasmic reticulum
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| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
140 - 141 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
0.0635 mg/mL |
Not Available |
| LogP |
3.23 |
HANSCH,C ET AL. (1995) |
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| Predicted Properties |
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| Spectra |
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| Biological Properties |
| Cellular Locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
- Endoplasmic reticulum
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| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Saliva
- Urine
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| Tissue Location |
- Muscle
- Fibroblasts
- Neuron
- Placenta
- Testes
- Kidney
- Liver
- Epidermis
- Brain
- Prostate
- Adrenal Gland
- Adipose Tissue
- Adrenal Cortex
- Platelet
- Gonads
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| Pathways |
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| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.020 +/- 0.011 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.001 (0.00034-0.0017) uM |
Children (1-13 year old) |
Female |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.0087 (0.0035-0.013) uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.023 (0.005-0.042) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00101 (0.00002-0.002) uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Saliva |
Detected and Quantified |
|
0.0033 (0.0024-0.0090) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.10 (0.066-0.17) umol/mmol creatinine |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.022 (0.017-0.041) umol/mmol creatinine |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.13 +/- 0.057 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.0016 +/- 0.00026 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00114 +/- 0.000630 uM |
Adult (>18 years old) |
Not Specified |
Leuprolide acetate-induce hypogonadism |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00127 +/- 0.00128 uM |
Adult (>18 years old) |
Not Specified |
Leuprolide acetate-induced hypogonadism with testosterone replacment |
Not Available |
| Urine |
Detected and Quantified |
|
0.00032 +/- 0.000065 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Rheumatoid arthritis |
Rheumatoid arthritis with prednisolone treatment
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| Urine |
Detected and Quantified |
|
0.00066 +/- 0.00021 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Rheumatoid arthritis |
Rheumatoid arthritis without prednisolone...
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| Urine |
Detected and Quantified |
|
0.00034 +/- 0.000078 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Systemic lupus erythematosus (SLE) |
Systemic lupus erythematosus (SLE) with...
|
| Urine |
Detected and Quantified |
|
0.0011 +/- 0.00026 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Systemic lupus erythematosus (SLE) |
Systemic lupus erythematosus (SLE) without...
|
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| Associated Disorders and Diseases |
| Disease References |
| Rheumatoid arthritis |
- Straub RH, Weidler C, Demmel B, Herrmann M, Kees F, Schmidt M, Scholmerich J, Schedel J: Renal clearance and daily excretion of cortisol and adrenal androgens in patients with rheumatoid arthritis and systemic lupus erythematosus. Ann Rheum Dis. 2004 Aug;63(8):961-8.
Pubmed: 15249323
|
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| Associated OMIM IDs |
|
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB021808 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
8036443  |
| KEGG Compound ID |
C01227  |
| BioCyc ID |
DEHYDRO-EPIANDROSTERONE-SULFATE  |
| BiGG ID |
37131  |
| Wikipedia Link |
Dehydroepiandrosterone  |
| NuGOwiki Link |
HMDB00077  |
| Metagene Link |
HMDB00077  |
| METLIN ID |
5133  |
| PubChem Compound |
9860744  |
| PDB ID |
Not Available |
| ChEBI ID |
220467  |
| References |
| Synthesis Reference |
Nguyen Xuan Cuong; Nguyen Van Dan. Synthesis of dehydroepiandrosterone (DHA) from 16-dehydropregnenolone acetate (DPA). Tap Chi Duoc Hoc (1983), (4), 12-14. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Robinzon B, Michael KK, Ripp SL, Winters SJ, Prough RA: Glucocorticoids inhibit interconversion of 7-hydroxy and 7-oxo metabolites of dehydroepiandrosterone: a role for 11beta-hydroxysteroid dehydrogenases? Arch Biochem Biophys. 2003 Apr 15;412(2):251-8.
Pubmed: 12667489
- Rao MS, Subbarao V, Yeldandi AV, Reddy JK: Hepatocarcinogenicity of dehydroepiandrosterone in the rat. Cancer Res. 1992 May 15;52(10):2977-9.
Pubmed: 1316232
- Saruc M, Yuceyar H, Ayhan S, Turkel N, Tuzcuoglu I, Can M: The association of dehydroepiandrosterone, obesity, waist-hip ratio and insulin resistance with fatty liver in postmenopausal women--a hyperinsulinemic euglycemic insulin clamp study. Hepatogastroenterology. 2003 May-Jun;50(51):771-4.
Pubmed: 12828082
- Bamberg E, Aichinger A, Mitteregger G: In vitro metabolism of dehydroepiandrosterone and testosterone by canine hair follicle cells. Vet Dermatol. 2004 Feb;15(1):19-24.
Pubmed: 14989701
- Gordon GB, Bush TL, Helzlsouer KJ, Miller SR, Comstock GW: Relationship of serum levels of dehydroepiandrosterone and dehydroepiandrosterone sulfate to the risk of developing postmenopausal breast cancer. Cancer Res. 1990 Jul 1;50(13):3859-62.
Pubmed: 2141293
- Schwarz S, Pohl P: Steroid hormones and steroid hormone binding globulins in cerebrospinal fluid studied in individuals with intact and with disturbed blood-cerebrospinal fluid barrier. Neuroendocrinology. 1992 Feb;55(2):174-82.
Pubmed: 1620285
- Weill-Engerer S, David JP, Sazdovitch V, Liere P, Schumacher M, Delacourte A, Baulieu EE, Akwa Y: In vitro metabolism of dehydroepiandrosterone (DHEA) to 7alpha-hydroxy-DHEA and Delta5-androstene-3beta,17beta-diol in specific regions of the aging brain from Alzheimer's and non-demented patients. Brain Res. 2003 Apr 18;969(1-2):117-25.
Pubmed: 12676372
- Finlay EM, Morton MS, Gaskell SJ: Identification and quantification of dehydroepiandrosterone sulphate in saliva. Steroids. 1982 Jan;39(1):63-71.
Pubmed: 6210977
- Uzieblo-Zyczkowska B, Sidlo E, Stelmaszuk T: [Dehydroepiandrosterone (DHEA)--slows down the aging process?] Pol Merkur Lekarski. 2005 Dec;19(114):831-4.
Pubmed: 16521435
- Prost O, Nicollier M, Laurent R, Adessi GL: Estrone- and dehydroepiandrosterone-sulfatase activities in human female epidermis. Arch Dermatol Res. 1985;277(3):195-200.
Pubmed: 3160310
- Friess E, Schiffelholz T, Steckler T, Steiger A: Dehydroepiandrosterone--a neurosteroid. Eur J Clin Invest. 2000 Dec;30 Suppl 3:46-50.
Pubmed: 11281367
- Hakkinen A, Pakarinen A, Hannonen P, Kautiainen H, Nyman K, Kraemer WJ, Hakkinen K: Effects of prolonged combined strength and endurance training on physical fitness, body composition and serum hormones in women with rheumatoid arthritis and in healthy controls. Clin Exp Rheumatol. 2005 Jul-Aug;23(4):505-12.
Pubmed: 16095120
- Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17.
Pubmed: 14625002
- Kim SB, Hill M, Kwak YT, Hampl R, Jo DH, Morfin R: Neurosteroids: Cerebrospinal fluid levels for Alzheimer's disease and vascular dementia diagnostics. J Clin Endocrinol Metab. 2003 Nov;88(11):5199-206.
Pubmed: 14602750
- Chalbot S, Morfin R: Human liver S9 fractions: metabolism of dehydroepiandrosterone, epiandrosterone, and related 7-hydroxylated derivatives. Drug Metab Dispos. 2005 Apr;33(4):563-9. Epub 2005 Jan 13.
Pubmed: 15650074
- Miller KK, Cai J, Ripp SL, Pierce WM Jr, Rushmore TH, Prough RA: Stereo- and regioselectivity account for the diversity of dehydroepiandrosterone (DHEA) metabolites produced by liver microsomal cytochromes P450. Drug Metab Dispos. 2004 Mar;32(3):305-13.
Pubmed: 14977864
- Martina V, Benso A, Gigliardi VR, Masha A, Origlia C, Granata R, Ghigo E: Short-term dehydroepiandrosterone treatment increases platelet cGMP production in elderly male subjects. Clin Endocrinol (Oxf). 2006 Mar;64(3):260-4.
Pubmed: 16487434
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