dehydroandrosterone

{{Short description|Chemical compound}}

{{Distinguish|Dehydroepiandrosterone}}

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| ImageFile = Dehydroandrosterone.svg

| ImageSize = 200px

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| IUPACName = 3α-Hydroxyandrost-5-en-17-one

| SystematicName = (3aS,3bR,7R,9aR,9bS,11aS)-7-Hydroxy-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-one

| OtherNames = DHA; 5-Dehydroandrosterone; 5-DHA; Androst-5-en-3α-ol-17-one; Isoandrostenolone

| Section1 = {{Chembox Identifiers

| CASNo = 2283-82-1

| ChemSpiderID = 118560

| PubChem = 134506

| StdInChI = 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+/m1/s1

| StdInChIKey = FMGSKLZLMKYGDP-HKQXQEGQSA-N

| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@H](C4)O)C

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| Section2 = {{Chembox Properties

| C=19 | H=28 | O=2

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| Section3 = {{Chembox Hazards

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Dehydroandrosterone (DHA), or 5-dehydroandrosterone (5-DHA), also known as isoandrostenolone, as well as androst-5-en-3α-ol-17-one, is an endogenous androgen steroid hormone.{{cite HMDB|author1-link=David S. Wishart|url=http://www.hmdb.ca/metabolites/HMDB05962|title=Showing metabocard for Dehydroandrosterone (HMDB05962)}}{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=641–}} It is the 3α-epimer of dehydroepiandrosterone (DHEA; androst-5-en-3β-ol-17-one) and the 5(6)-dehydrogenated and non-5α-reduced analogue of androsterone (5α-androstan-3α-ol-17-one). DHA is produced in and secreted from the adrenal glands, along with other weak androgens like DHEA, androstenediol, and androstenedione.{{cite book|author1=Alfred E. Chang|author2=Patricia A. Ganz|author3=Daniel F. Hayes |author4=Timothy Kinsella |author5=Harvey I. Pass |author6=Joan H. Schiller |author7=Richard M. Stone |author8=Victor Strecher |title=Oncology: An Evidence-Based Approach|url=https://books.google.com/books?id=vxh6u1-ETk0C&pg=PA75|date=8 December 2007|publisher=Springer Science & Business Media|isbn=978-0-387-31056-5|pages=75–}}