Dehydroandrosterone

Not to be confused with Dehydroepiandrosterone.

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]

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
CAS Number	2283-82-1
3D model (JSmol)	Interactive image
ChemSpider	118560
PubChem CID	134506
CompTox Dashboard (EPA)	DTXSID20177384
InChI 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
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@H](C4)O)C
Properties
Chemical formula	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

• 3α-Androstanediol
• Epiandrosterone

References

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. 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.