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

2024-10-11 03:38:52 UTC

Metabolite 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

Value	Source
3-BETA-HYDROXY-5-androsten-17-one	ChEBI
3beta-Hydroxyandrost-5-en-17-one	ChEBI
Dehydroisoandrosterone	ChEBI
DHA	ChEBI
DHEA	ChEBI
Intrarosa	ChEBI
Prasterone	ChEBI
Biolaif	Kegg
3-b-HYDROXY-5-androsten-17-one	Generator
3-Β-hydroxy-5-androsten-17-one	Generator
3b-Hydroxyandrost-5-en-17-one	Generator
3Β-hydroxyandrost-5-en-17-one	Generator
(+)-Dehydroisoandrosterone	HMDB
(3-beta)-3-Hydroxyandrost-5-en-17-one	HMDB
(3beta)-3-Hydroxy-androst-5-en-17-one	HMDB
(3beta,16alpha)-3,16-Dihydroxy-androst-5-en-17-one	HMDB
17-Chetovis	HMDB
17-Hormoforin	HMDB
3-beta-Hydroxyandrost-5-en-17-one	HMDB
3b-Hydroxy-D5-androsten-17-one	HMDB
3beta-Hydroxy-5-androsten-17-one	HMDB
3beta-Hydroxy-androst-5-en-17-one	HMDB
3beta-Hydroxy-D5-androsten-17-one	HMDB
5,6-Dehydroisoandrosterone	HMDB
5,6-Didehydroisoandrosterone	HMDB
5-Androsten-3-beta-ol-17-one	HMDB
5-Androsten-3b-ol-17-one	HMDB
5-Androsten-3beta-ol-17-one	HMDB
5-Dehydro-epiandrosterone	HMDB
5-Dehydroepiandrosterone	HMDB
Andrestenol	HMDB
Androst-5-ene-3b-ol-17-one	HMDB
Androst-5-ene-3beta-ol-17-one	HMDB
Androsten-3beta-ol-17-one	HMDB
Androstenolone	HMDB
Astenile	HMDB
D5-Androsten-3b-ol-17-one	HMDB
D5-Androsten-3beta-ol-17-one	HMDB
Deandros	HMDB
Dehydro-epi-androsterone	HMDB
Diandron	HMDB
Diandrone	HMDB
Hydroxyandrostenone	HMDB
Prasterona	HMDB
Prasteronum	HMDB
Prestara	HMDB
Psicosterone	HMDB
trans-Dehydroandrosterone	HMDB
Prasterone, 3 alpha-isomer	HMDB
5 Androsten 3 beta hydroxy 17 one	HMDB
5-Androsten-3-beta-hydroxy-17-one	HMDB
5 Androsten 3 ol 17 one	HMDB
Prasterone, 3 alpha isomer	HMDB
5-Androsten-3-ol-17-one	HMDB
EM-760Dehydroandrosterone	HMDB

Molecular Formula

C₁₉H₂₈O₂

Average Mass

288.4244

Monoisotopic Mass

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

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Oxosteroid
17-oxosteroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:28689 )
17-oxo steroid (CHEBI:28689 )
androstanoid (CHEBI:28689 )
C19 steroids (androgens) and derivatives (C01227 )
Androstane and derivatives (C01227 )
Androgens (C01227 )
C19 steroids (androgens) and derivatives (LMST02020021 )

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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192023	Sulfotransferase family cytosolic 2B member 1	Enzyme	O00204	Homo sapiens
MMDBp0192108	Solute carrier organic anion transporter family member 1B3	Transporter	Q9NPD5	Homo sapiens
MMDBp0192115	Solute carrier organic anion transporter family member 1B1	Transporter	Q9Y6L6	Homo sapiens
MMDBp0192150	Steryl-sulfatase	Unknown	P08842	Homo sapiens
MMDBp0192158	Cholesterol 7-alpha-monooxygenase	Unknown	P22680	Homo sapiens
MMDBp0192653	Steroid 17-alpha-hydroxylase/17,20 lyase	Unknown	P05093	Homo sapiens
MMDBp0193970	3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1	Unknown	P14060	Homo sapiens
MMDBp0193971	3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2	Unknown	P26439	Homo sapiens
MMDBp0195820	Solute carrier family 22 member 7	Transporter	Q9Y694	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000676	Dehydroepiandrosterone	Dehydroepiandrosterone sulfate	sulfotransferase family, cytosolic, 1A, phenol-preferring, member 3	VMH; KEGG	11535246 1588921
MMDBr0001845	17a-Hydroxypregnenolone	Acetaldehyde	cytochrome P450, family 17, subfamily A, polypeptide 1	VMH	12915666 7893148
MMDBr0002177	Dehydroepiandrosterone sulfate	Dehydroepiandrosterone	Not Available	VMH; KEGG	30371894
MMDBr0002178	Dehydroepiandrosterone sulfate	Dehydroepiandrosterone	steroid sulfatase (microsomal), isozyme S	VMH; KEGG	30371894
MMDBr0003957	17a-Hydroxypregnenolone	Acetic acid	Not Available	VMH	10049998 7578007
MMDBr0003958	17a-Hydroxypregnenolone	Acetic acid	cytochrome P450, family 17, subfamily A, polypeptide 1	VMH	10049998 7578007
MMDBr0003959	17a-Hydroxypregnenolone	Acetic acid	cytochrome P450, family 17, subfamily A, polypeptide 1	VMH	10049998 7578007
MMDBr0009617	17a-Hydroxypregnenolone	Acetaldehyde	cytochrome P450, family 17, subfamily A, polypeptide 1	VMH; KEGG	30371894
MMDBr0009619	Dehydroepiandrosterone	androst-5-ene-3,17-dione	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	VMH	30371894
MMDBr0009620	Dehydroepiandrosterone	androst-5-ene-3,17-dione	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
21-hydroxylase deficiency	Decreased	Association	Human Blood	HMDB	11826238
Rheumatoid arthritis	Decreased	Association	Human Urine	HMDB	15249323

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	45	Human feces; Human sputum; Human unknown; Human	Metabolic reconstruction
Bacteria	Bacteroidetes	24	Human feces; Human appendix biopsy; Human ; Human stool	Metabolic reconstruction
Bacteria	Firmicutes	32	Human feces; Human	Metabolic reconstruction
Bacteria	Actinobacteria	12	Human feces; Human	Metabolic reconstruction
Bacteria	Fusobacteria	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0000077

DrugBank ID

DB01708

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021808

KNApSAcK ID

Not Available

Chemspider ID

8036443

KEGG Compound ID

C01227

BioCyc ID

3-BETA-HYDROXYANDROST-5-EN-17-ONE

BiGG ID

37131

Wikipedia Link

Dehydroepiandrosterone

METLIN ID

5133

PubChem Compound

5881

PDB ID

Not Available

ChEBI ID

28689

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:0x00007f46d6c6b258>

3D MOL for #<Metabolite:0x00007f46d6c6b258>

3D SDF for #<Metabolite:0x00007f46d6c6b258>

3D-SDF for #<Metabolite:0x00007f46d6c6b258>

PDB for #<Metabolite:0x00007f46d6c6b258>

3D PDB for #<Metabolite:0x00007f46d6c6b258>

SMILES for #<Metabolite:0x00007f46d6c6b258>

INCHI for #<Metabolite:0x00007f46d6c6b258>

Structure for #<Metabolite:0x00007f46d6c6b258>

3D Structure for #<Metabolite:0x00007f46d6c6b258>