MiMeDB: Showing metabocard for Dehydroepiandrosterone sulfate (MMDBc0000561)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:34 UTC

Update Date

2024-10-13 14:35:40 UTC

Metabolite ID

MMDBc0000561

Metabolite Identification

Common Name

Dehydroepiandrosterone sulfate

Description

Dehydroepiandrosterone sulfate or DHEA-S is the sulfated form of dehydroepiandrosterone (DHEA). This sulfation is reversibly catalyzed by sulfotransferase 2A1 (SULT2A1) primarily in the adrenals, the liver, and small intestine. In the blood, most DHEA is found as DHEA-S with levels that are about 300 times higher than those of free DHEA. Orally-ingested DHEA is converted into its sulfate when passing through the intestines and liver. Whereas DHEA levels naturally reach their peak in the early morning hours, DHEAS levels show no diurnal variation. From a practical point of view, measurement of DHEA-S is preferable to DHEA since levels are more stable. DHEA (from which DHEA-S comes from) is a natural steroid prohormone produced from cholesterol by the adrenal glands, the gonads, adipose tissue, brain, and in the skin (by an autocrine mechanism). DHEA is the precursor of androstenedione, which can undergo further conversion to produce the androgen testosterone and the estrogens estrone and estradiol. DHEA is also a potent sigma-1 agonist. Serum dehydroepiandrosterone sulfate is a classic marker for adrenarche, and subsequently for the individual hormonal milieu (PMID: 10599744 ). Dehydroepiandrosterone sulfate is an endogenously produced sex steroid that has been hypothesized to have anti-aging effects (PMID: 16960027 ). It also has been inversely associated with the development of atherosclerosis (PMID: 8956025 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₁₉H₂₈O₅S

Average Mass

368.488

Monoisotopic Mass

368.165744696

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1

InChI Key

CZWCKYRVOZZJNM-USOAJAOKSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Kidney
Liver
Placenta
Prostate
Urine

Tissue Locations

Kidney
Liver
Placenta
Prostate

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
MMDBp0192150	Steryl-sulfatase	Unknown	P08842	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
MMDBr0002177	Dehydroepiandrosterone sulfate	Dehydroepiandrosterone	Not Available	VMH; KEGG	30371894
MMDBr0002178	Dehydroepiandrosterone sulfate	Dehydroepiandrosterone	steroid sulfatase (microsomal), isozyme S	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
11-beta-hydroxylase deficiency		Association	Human Blood	HMDB	8933406
Alzheimer's disease	Slight Increase	Association	Human Blood	HMDB	8478958
Hirsutism	Increased	Association	Human Blood	HMDB	8187312
Polycystic ovary syndrome		Association	Human Blood	HMDB	15531511
Rheumatoid arthritis	Decreased	Association	Human Urine	HMDB	15249323

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	34	Human ; Human feces; Human stool; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
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	Actinobacteria	10	Human feces	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	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

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	20				uM	Newborn (0-30 days old)	Female	11-beta-hydroxylase deficiency	HMDB	8933406
Human Blood	Detected and Quantified			2.000	10.400	uM	Children (1-13 years old)	Both	11-beta-hydroxylase deficiency	HMDB	8933406
Human Blood	Detected and Quantified	5.493				uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	7951484
Human Blood	Detected and Quantified			42.0638	105.0238	uM	Newborn (0-30 days old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	27476613
Human Blood	Detected and Quantified	6.54	2.55			uM	Adult (>18 years old)	Female	Alzheimer's disease	HMDB	8478958
Human Blood	Detected and Quantified	<0.810				uM	Children (1-13 years old)	Female	Aromatase deficiency	HMDB	9177373
Human Blood	Detected and Quantified	0.0621				uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 17-alpha-hydroxylase deficiency	HMDB	26161337
Human Blood	Detected and Quantified	0.104				uM	Adolescent (13-18 years old)	Female	Adrenal hyperplasia, congenital, due to 17-alpha-hydroxylase deficiency	HMDB	26161337
Human Blood	Detected and Quantified	9.8	1.3			uM	Adult (>18 years old)	Female	Hirsutism	HMDB	8187312
Human Blood	Detected and Quantified	<0.02				uM	Adult (>18 years old)	Female	Lipoid Adrenal Hyperplasia	HMDB	9077535
Human Blood	Detected and Quantified	<0.02				uM	Adolescent (13-18 years old)	Female	Lipoid Adrenal Hyperplasia	HMDB	9077535
Human Blood	Detected and Quantified	3.63	2.14			uM	Adult (>18 years old)	Female	Polycystic ovary syndrome (PCOS)	HMDB	15531511
Human Urine	Detected and Quantified	0.28	0.082			umol/mmol creatinine	Adult (>18 years old)	Both	Rheumatoid arthritis	HMDB	15249323
Human Urine	Detected and Quantified	0.84	0.51			umol/mmol creatinine	Adult (>18 years old)	Both	Rheumatoid arthritis	HMDB	15249323
Human Blood	Detected and Quantified			3.400	15	uM	Adult (>18 years old)	Male	X-linked ichthyosis	HMDB	3864567
Human Blood	Detected and Quantified	<0.500				uM	Not Specified	Both	Normal	HMDB	8933406
Human Blood	Detected and Quantified			0.950	11.669	uM	Adult (>18 years old)	Female	Normal	HMDB	26161337
Human Urine	Detected and Quantified	1.25		0.0026	2.52	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	18501914
Human Urine	Detected and Quantified	1.34	0.23			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15249323
Human Blood	Detected and Quantified	3.47	1.20			uM	Adult (>18 years old)	Female	Normal	HMDB	15531511
Human Blood	Detected and Quantified	4.5		1.4	8.2	uM	Adult (>18 years old)	Female	Normal	HMDB	8187312
Human Blood	Detected and Quantified			0	3.26	uM	Children (1 - <6 years old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			0.27	4.34	uM	Children (6 - <9 years old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			0.27	4.89	uM	Infant (6 months - <1 year old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			0.81	16.28	uM	Infant (2 - <6 months old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			0.81	7.60	uM	Children (9 - <13 years old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			1.63	13.03	uM	Adolescent (13 - <16 years old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			28.9	40.7	uM	Newborn (0-30 days old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			3.53	16.01	uM	Adolescent (16 - <19 years old)	Male	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			4.07	16.01	uM	Adolescent (16 - <19 years old)	Female	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			0.950	1.167	uM	Adult (>18 years old)	Both	Normal	HMDB	Vancouver Coastal Health Lab (http://www.vch.ca/Locations-Services/result?res_id=601)
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 Placenta	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 Blood	Detected but not Quantified						Adult (>18 years old)	Female	Normal	HMDB	22944140
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
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

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

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 ]
Milewich L, Sontheimer RD, Herndon JH Jr: Steroid sulfatase activity in epidermis of acne-prone and non-acne-prone skin of patients with acne vulgaris. Arch Dermatol. 1990 Oct;126(10):1312-4. [PubMed:2145810 ]
Zappulla F, Ventura D, Capelli M, Cassio A, Balsamo A, Frejaville E, Bolelli G, Cacciari E: Gonadal and adrenal secretion of dehydroepiandrosterone sulfate in prepubertal and pubertal subjects. J Endocrinol Invest. 1981 Apr-Jun;4(2):197-202. doi: 10.1007/BF03350452. [PubMed:6268694 ]
Gu H, Li Y, Rong L: [The effect of sodium prasterone sulfate on lactation]. Zhonghua Fu Chan Ke Za Zhi. 1995 Apr;30(4):197-9. [PubMed:7664601 ]
Jaquish CE, Blangero J, Haffner SM, Stern MP, Maccluer JW: Quantitative genetics of dehydroepiandrosterone sulfate and its relation to possible cardiovascular disease risk factors in Mexican Americans. Hum Hered. 1996 Nov-Dec;46(6):301-9. doi: 10.1159/000154368. [PubMed:8956025 ]
De Pergola G, Zamboni M, Sciaraffia M, Turcato E, Pannacciulli N, Armellini F, Giorgino F, Perrini S, Bosello O, Giorgino R: Body fat accumulation is possibly responsible for lower dehydroepiandrosterone circulating levels in premenopausal obese women. Int J Obes Relat Metab Disord. 1996 Dec;20(12):1105-10. [PubMed:8968856 ]
Coulter CL, Jaffe RB: Functional maturation of the primate fetal adrenal in vivo: 3. Specific zonal localization and developmental regulation of CYP21A2 (P450c21) and CYP11B1/CYP11B2 (P450c11/aldosterone synthase) lead to integrated concept of zonal and temporal steroid biosynthesis. Endocrinology. 1998 Dec;139(12):5144-50. doi: 10.1210/endo.139.12.6333. [PubMed:9832454 ]
Roberts E: The importance of being dehydroepiandrosterone sulfate (in the blood of primates): a longer and healthier life? Biochem Pharmacol. 1999 Feb 15;57(4):329-46. doi: 10.1016/s0006-2952(98)00246-9. [PubMed:9933021 ]
Ankarberg C, Norjavaara E: Diurnal rhythm of testosterone secretion before and throughout puberty in healthy girls: correlation with 17beta-estradiol and dehydroepiandrosterone sulfate. J Clin Endocrinol Metab. 1999 Mar;84(3):975-84. doi: 10.1210/jcem.84.3.5524. [PubMed:10084582 ]
Benvenga S, Smedile G, Lo Giudice F, Trimarchi F: Testicular adrenal rests: evidence for luteinizing hormone receptors and for distinct types of testicular nodules differing for their autonomization. Eur J Endocrinol. 1999 Sep;141(3):231-7. doi: 10.1530/eje.0.1410231. [PubMed:10474120 ]
Wang HS, Wang TH, Soong YK: Low dose flutamide in the treatment of acne vulgaris in women with or without oligomenorrhea or amenorrhea. Changgeng Yi Xue Za Zhi. 1999 Sep;22(3):423-32. [PubMed:10584414 ]
Ibanez L, Potau N, Marcos MV, de Zegher F: Exaggerated adrenarche and hyperinsulinism in adolescent girls born small for gestational age. J Clin Endocrinol Metab. 1999 Dec;84(12):4739-41. doi: 10.1210/jcem.84.12.6341. [PubMed:10599744 ]
Chang HJ, Shi R, Rehse P, Lin SX: Identifying androsterone (ADT) as a cognate substrate for human dehydroepiandrosterone sulfotransferase (DHEA-ST) important for steroid homeostasis: structure of the enzyme-ADT complex. J Biol Chem. 2004 Jan 23;279(4):2689-96. doi: 10.1074/jbc.M310446200. Epub 2003 Oct 21. [PubMed:14573603 ]
Zouboulis CC, Degitz K: Androgen action on human skin -- from basic research to clinical significance. Exp Dermatol. 2004;13 Suppl 4:5-10. doi: 10.1111/j.1600-0625.2004.00255.x. [PubMed:15507105 ]
Rainey WE, Rehman KS, Carr BR: The human fetal adrenal: making adrenal androgens for placental estrogens. Semin Reprod Med. 2004 Nov;22(4):327-36. doi: 10.1055/s-2004-861549. [PubMed:15635500 ]
Clauss SB, Holmes KW, Hopkins P, Stein E, Cho M, Tate A, Johnson-Levonas AO, Kwiterovich PO: Efficacy and safety of lovastatin therapy in adolescent girls with heterozygous familial hypercholesterolemia. Pediatrics. 2005 Sep;116(3):682-8. doi: 10.1542/peds.2004-2090. [PubMed:16140708 ]
Sipila S, Heikkinen E, Cheng S, Suominen H, Saari P, Kovanen V, Alen M, Rantanen T: Endogenous hormones, muscle strength, and risk of fall-related fractures in older women. J Gerontol A Biol Sci Med Sci. 2006 Jan;61(1):92-6. doi: 10.1093/gerona/61.1.92. [PubMed:16456199 ]
Dalla Valle L, Toffolo V, Nardi A, Fiore C, Bernante P, Di Liddo R, Parnigotto PP, Colombo L: Tissue-specific transcriptional initiation and activity of steroid sulfatase complementing dehydroepiandrosterone sulfate uptake and intracrine steroid activations in human adipose tissue. J Endocrinol. 2006 Jul;190(1):129-39. doi: 10.1677/joe.1.06811. [PubMed:16837617 ]
Cutolo M, Sulli A, Capellino S, Villaggio B, Montagna P, Pizzorni C, Paolino S, Seriolo B, Felli L, Straub RH: Anti-TNF and sex hormones. Ann N Y Acad Sci. 2006 Jun;1069:391-400. doi: 10.1196/annals.1351.037. [PubMed:16855166 ]
Cappola AR, Xue QL, Walston JD, Leng SX, Ferrucci L, Guralnik J, Fried LP: DHEAS levels and mortality in disabled older women: the Women's Health and Aging Study I. J Gerontol A Biol Sci Med Sci. 2006 Sep;61(9):957-62. doi: 10.1093/gerona/61.9.957. [PubMed:16960027 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Dehydroepiandrosterone sulfate (MMDBc0000561)

MOL for #<Metabolite:0x00007f5394173308>

3D MOL for #<Metabolite:0x00007f5394173308>

3D SDF for #<Metabolite:0x00007f5394173308>

3D-SDF for #<Metabolite:0x00007f5394173308>

PDB for #<Metabolite:0x00007f5394173308>

3D PDB for #<Metabolite:0x00007f5394173308>

SMILES for #<Metabolite:0x00007f5394173308>

INCHI for #<Metabolite:0x00007f5394173308>

Structure for #<Metabolite:0x00007f5394173308>

3D Structure for #<Metabolite:0x00007f5394173308>