P7754
5α-Pregnane-3,20-dione (allo)
progesterone metabolite
Synonym(s):
5α-Dihydroprogesterone, Allopregnane-3,20-dione
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About This Item
Empirical Formula (Hill Notation):
C21H32O2
CAS Number:
Molecular Weight:
316.48
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
51111800
EC Number:
209-297-3
MDL number:
Quality Segment
form
powder
SMILES string
[H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@H](C(C)=O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CCC(=O)C2
InChI
1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1
InChI key
XMRPGKVKISIQBV-BJMCWZGWSA-N
Biochem/physiol Actions
A high-level metabolite of progesterone in breast cancer tissue (but not normal breast tissue); promotes cell proliferation and detachment. Receptors appear only on the cell surface of MCF-7 breast cancer cells, not on nuclei where most other steroid receptors are located.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Related Content
J Zhang et al.
The Journal of steroid biochemistry and molecular biology, 70(4-6), 123-131 (2000-01-06)
Progesterone inhibits intracellular transport of lysosomal cholesterol in cultured cells, and thus at least in part mimics the biochemical phenotype of Niemann-Pick type C disease (NPC) in human fibroblasts. The goal of this study was to determine whether metabolism of
George Wittemyer et al.
Hormones and behavior, 51(3), 346-354 (2007-02-27)
Non-invasive endocrine methods enable investigation of the relationship between ecological variation and ovarian activity and how this impacts on demographic processes. The underlying physiological factors driving high variation in inter-calving intervals among multi-parous African elephants offer an interesting system for
Laurence Meyer et al.
Cellular and molecular life sciences : CMLS, 67(17), 3017-3034 (2010-05-01)
Painful neuropathy is a major side-effect limiting cancer chemotherapy. Therefore, novel strategies are required to suppress the neuropathic effects of anticancer drugs without altering their chemotherapeutic effectiveness. By combining biochemical, neuroanatomical/neurochemical, electrophysiological and behavioral methods, we demonstrated that progesterone-derived neurosteroids