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Dehydroandrosterone

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Not to be confused with Dehydroepiandrosterone.
Dehydroandrosterone
Names
IUPAC name
(3R,8R,9S,10R,13S,14S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
Other names
DHA; 5-Dehydroandrosterone; 5-DHA; Androst-5-en-3α-ol-17-one; 3α-Hydroxyandrost-5-en-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 mass 288.431 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[1][2] 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).[2] DHA is produced in and secreted from the adrenal glands, along with other weak androgens like DHEA, androstenediol, and androstenedione.[3]

See also

References

  1. ^ http://www.hmdb.ca/metabolites/HMDB05962
  2. ^ a b J. 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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