Dehydroandrosterone

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]

Not to be confused with Dehydroepiandrosterone.
Dehydroandrosterone
Names
Preferred 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; 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).
Infobox references

See also

References
  1. Wishart, David S.; Djombou Feunang, Yannick; Marcu, Ana; Guo, An Chi; Liang, Kevin; Vázquez Fresno, Rosa; Sajed, Tanvir; Johnson, Daniel; Li, Carin; Karu, Naama; Sayeeda, Zinat; Lo, Elvis; Assempour, Nazanin; Berjanskii, Mark; Singhal, Sandeep; Arndt, David; Liang, Yonjie; Badran, Hasan; Grant, Jason; Serra Cayuela, Arnau; Liu, Yifeng; Mandal, Rupa; Neveu, Vanessa; Pon, Allison; Knox, Craig; Wilson, Michael; Manach, Claudine; Scalbert, Augustin. "Showing metabocard for Dehydroandrosterone (HMDB05962)". Human Metabolome Database, HMDB. 4.0.
  2. 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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