MiMeDB: Showing metabocard for Dehydroepiandrosterone (MMDBc0047901)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:06:00 UTC

Update Date

2022-09-01 02:00:45 UTC

MiMeDB ID

MMDBc0047901

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 or DHEA-S) before secretion. DHEA-S 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 DHEA-S with levels that are about 300 times higher than free DHEA. Blood measurements of DHEA-S/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 DHEA-S.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₉H₂₈O₂

Average Molecular Weight

288.4244

Monoisotopic Molecular Weight

288.20893014

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

53-43-0

SMILES

Not Available

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-USOAJAOKSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Blood
Brain
Cerebrospinal Fluid (CSF)
Epidermis
Feces
Fibroblasts
Kidney
Liver
Neuron
Ovary
Placenta
Platelet
Prostate
Saliva
Skeletal Muscle
Testis
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Brain
Epidermis
Fibroblasts
Kidney
Liver
Neuron
Ovary
Placenta
Platelet
Prostate
Skeletal Muscle
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

#<MetaboliteProteinLink:0x0000564abc153530>

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference
21-Hydroxylase deficiency	Decreased	This associated disease is originally imported from HMDB metabolite HMDB0000077 concentration id 141626	Association	Human Blood		11826238	details
Rheumatoid arthritis	Decreased	This associated disease is originally imported from HMDB metabolite HMDB0000077 concentration id 58599	Association	Human Urine		15249323	details

Microbial Sources

Phylum	Total species	Hosts and Body Sites	Microbial Links
Proteobacteria	45	Human Feces; Human	Metabolic reconstruction
Bacteroidetes	24	Human Feces; Human	Metabolic reconstruction
Firmicutes	32	Human Feces; Human	Metabolic reconstruction
Actinobacteria	12	Human Feces; Human	Metabolic reconstruction;
Fusobacteria	2	Human Feces	Metabolic reconstruction
Euryarchaeota	1	Human Feces	Metabolic reconstruction
Planctomycetes	1	Human Feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB		details
Human	Detected and Quantified			0.00250	0.00284	Adult (>18 years old)	Female	21-hydroxylase deficiency	HMDB	11826238	details
Human	Detected and Quantified	0.052				Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224	details
Human	Detected and Quantified	0.653				Adolescent (13-18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224	details
Human	Detected and Quantified	0.00150	0.00120			Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224	details
Human	Detected and Quantified			0.00157	0.385	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224	details
Human	Detected and Quantified	0.00246	0.00350			Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	26079780	details
Human	Detected and Quantified	0.00520	0.00740			Children (1-13 years old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224	details
Human	Detected and Quantified	0.00800	0.0100			Infant (0-1 year old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224	details
Human	Detected and Quantified	0.0103	0.0100			Newborn (0-30 days old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224	details
Human	Detected and Quantified	0.0120	0.00700			Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224	details
Human	Detected and Quantified	0.0140	0.00700			Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224	details
Human	Detected and Quantified			0.0184	0.0333	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	7951484	details
Human	Detected and Quantified			0.0226	0.407	Newborn (0-30 days old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224	details
Human	Detected and Quantified	0.0448	0.0655			Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	26079780	details
Human	Detected and Quantified	0.00101				Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	HMDB	18182448	details
Human	Detected and Quantified	0.0042				Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	HMDB	18182448	details
Human	Detected and Quantified			0.00240	0.00830	Infant (0-1 year old)	Both	Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis	HMDB	16439592	details
Human	Detected and Quantified	0.0016				Children (1-13 years old)	Female	Aromatase deficiency	HMDB	9177373	details
Human	Detected and Quantified	<0.00003				Adult (>18 years old)	Female	Lipoid Adrenal Hyperplasia	HMDB	9077535	details
Human	Detected and Quantified	<0.00003				Adolescent (13-18 years old)	Female	Lipoid Adrenal Hyperplasia	HMDB	9077535	details
Human	Detected and Quantified	0.00032	0.000065			Adult (>18 years old)	Both	Rheumatoid arthritis	HMDB	15249323	details
Human	Detected and Quantified	0.00066	0.00021			Adult (>18 years old)	Both	Rheumatoid arthritis	HMDB	15249323	details
Human	Detected and Quantified			0.000700	0.0204	Infant (0-1 year old)	Not Specified	Normal	HMDB	16439592	details
Human	Detected and Quantified	0.001		0.00034	0.0017	Children (1-13 years old)	Female	Normal	HMDB	14625002	details
Human	Detected and Quantified	0.00101		0.00002	0.002	Adult (>18 years old)	Not Specified	Normal	HMDB	1620285	details
Human	Detected and Quantified	0.0016	0.00026			Adult (>18 years old)	Both	Normal	HMDB	15249323	details
Human	Detected and Quantified			0.00173	0.0264	Newborn (0-30 days old)	Female	Normal	HMDB	18182448	details
Human	Detected and Quantified	0.0022		0.0006	0.0273	Newborn (0-30 days old)	Both	Normal	HMDB	23159298	details
Human	Detected and Quantified			0.00225	0.0433	Newborn (0-30 days old)	Female	Normal	HMDB	18182448	details
Human	Detected and Quantified	0.00295	0.00319			Children (1-13 years old)	Both	Normal	HMDB	26079780	details
Human	Detected and Quantified	0.0033		0.0024	0.0090	Adult (>18 years old)	Both	Normal	HMDB	6210977	details
Human	Detected and Quantified	0.0087		0.0035	0.013	Adult (>18 years old)	Female	Normal	HMDB	14625002	details
Human	Detected and Quantified	0.0146	0.00451			Adult (>18 years old)	Female	Normal	HMDB	7951484	details
Human	Detected and Quantified	0.0153	0.00763			Adult (>18 years old)	Female	Normal	HMDB	11826238	details
Human	Detected and Quantified	0.020	0.011			Adult (>18 years old)	Male	Normal	HMDB	17185878	details
Human	Detected and Quantified	0.022		0.017	0.041	Adult (>18 years old)	Female	Normal	HMDB	11085621	details
Human	Detected and Quantified	0.10		0.066	0.17	Adult (>18 years old)	Male	Normal	HMDB	11085621	details
Human	Detected and Quantified	0.13	0.057			Adult (>18 years old)	Both	Normal	HMDB	15560936	details
Human	Detected and Quantified	0.023		0.005	0.042	Adult (>18 years old)	Both	Normal	HMDB	The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.	details
Human Adipose Tissue	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Adrenal Cortex	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Adrenal Gland	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Brain	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Epidermis	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Fibroblasts	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Kidney	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Liver	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Neuron	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Ovary	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Placenta	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Platelet	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Prostate	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Skeletal Muscle	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Testis	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057	details
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057	details

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
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. doi: 10.1159/000126112. [PubMed:1620285 ]
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 ]
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. doi: 10.1007/BF00404316. [PubMed:3160310 ]
Finlay EM, Morton MS, Gaskell SJ: Identification and quantification of dehydroepiandrosterone sulphate in saliva. Steroids. 1982 Jan;39(1):63-71. doi: 10.1016/0039-128x(82)90126-x. [PubMed:6210977 ]
Friess E, Schiffelholz T, Steckler T, Steiger A: Dehydroepiandrosterone--a neurosteroid. Eur J Clin Invest. 2000 Dec;30 Suppl 3:46-50. doi: 10.1046/j.1365-2362.2000.0300s3046.x. [PubMed:11281367 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
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. doi: 10.1016/s0003-9861(03)00056-0. [PubMed:12667489 ]
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. doi: 10.1016/s0006-8993(03)02288-1. [PubMed:12676372 ]
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 ]
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. doi: 10.1210/jc.2003-030646. [PubMed:14602750 ]
Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. doi: 10.1016/s0039-128x(03)00115-6. [PubMed:14625002 ]
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. doi: 10.1124/dmd.32.3.305. [PubMed:14977864 ]
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. doi: 10.1111/j.1365-3164.2004.00366.x. [PubMed:14989701 ]
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. doi: 10.1124/dmd.104.003004. Epub 2005 Jan 13. [PubMed:15650074 ]
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 ]
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. doi: 10.1111/j.1365-2265.2006.02454.x. [PubMed:16487434 ]
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 ]
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. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
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. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Dehydroepiandrosterone (MMDBc0047901)

MOL for #<Metabolite:0x0000564abb478ef0>

3D MOL for #<Metabolite:0x0000564abb478ef0>

3D SDF for #<Metabolite:0x0000564abb478ef0>

3D-SDF for #<Metabolite:0x0000564abb478ef0>

PDB for #<Metabolite:0x0000564abb478ef0>

3D PDB for #<Metabolite:0x0000564abb478ef0>

SMILES for #<Metabolite:0x0000564abb478ef0>

INCHI for #<Metabolite:0x0000564abb478ef0>

Structure for #<Metabolite:0x0000564abb478ef0>

3D Structure for #<Metabolite:0x0000564abb478ef0>