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Chemical compound
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
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
C 19 H 28 O 2
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).
Chemical compound
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
^ 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.
^
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 .
^ 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 .
AR Tooltip Androgen receptor
Agonists
SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A