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Dehydroandrosterone

From Wikipedia, the free encyclopedia
Chemical compound
Not to be confused withDehydroepiandrosterone.
Dehydroandrosterone
Names
IUPAC name
3α-Hydroxyandrost-5-en-17-one
Systematic IUPAC name
(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
Other names
DHA; 5-Dehydroandrosterone; 5-DHA; Androst-5-en-3α-ol-17-one; Isoandrostenolone
Identifiers
3D model (JSmol)
ChemSpider
  • 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+/m1/s1
    Key: FMGSKLZLMKYGDP-HKQXQEGQSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@H](C4)O)C
Properties
C19H28O2
Molar mass288.431 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Dehydroandrosterone (DHA), or5-dehydroandrosterone (5-DHA), also known asisoandrostenolone, as well asandrost-5-en-3α-ol-17-one, is anendogenousandrogensteroid hormone.[1][2] It is the 3α-epimer ofdehydroepiandrosterone (DHEA; androst-5-en-3β-ol-17-one) and the 5(6)-dehydrogenated and non-5α-reducedanalogue ofandrosterone (5α-androstan-3α-ol-17-one).[2] DHA is produced in and secreted from theadrenal glands, along with other weak androgens like DHEA,androstenediol, andandrostenedione.[3]

See also

[edit]

References

[edit]
  1. ^Wishart, David S.; Guo, An Chi; Oler, Eponine; Wang, Fel; Anjum, Afia; Peters, Harrison; Dizon, Raynard; Sayeeda, Zinat; Tian, Siyang; Lee, Brian L.; Berjanskii, Mark; Mah, Robert; Yamamoto, Mai; Jovel Castillo, Juan; Torres Calzada, Claudia; Hiebert Giesbrecht, Mickel; Lui, Vicki W.; Varshavi, Dorna; Varshavi, Dorsa; Allen, Dana; Arndt, David; Khetarpal, Nitya; Sivakumaran, Aadhavya; Harford, Karxena; Sanford, Selena; Yee, Kristen; Cao, Xuan; Budinsky, Zachary; Liigand, Jaanus; Zhang, Lun; Zheng, Jiamin; Mandal, Rupasri; Karu, Naama; Dambrova, Maija; Schiöth, Helgi B.; Gautam, Vasuk."Showing metabocard for Dehydroandrosterone (HMDB05962)".Human Metabolome Database, HMDB. 5.0.
  2. ^abJ. Elks (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 641–.ISBN 978-1-4757-2085-3.
  3. ^Alfred E. Chang; Patricia A. Ganz; Daniel F. Hayes; Timothy Kinsella; Harvey I. Pass; Joan H. Schiller; Richard M. Stone; Victor Strecher (8 December 2007).Oncology: An Evidence-Based Approach. Springer Science & Business Media. pp. 75–.ISBN 978-0-387-31056-5.
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