Structure Database (LMSD)

Common Name
5alpha-pregnane-3,20-dione
Systematic Name
5α-pregnane-3,20-dione
Synonyms
  • 3,20-allopregnanedione
  • 3,20-dioxo-5alpha-pregnane
  • 5-alpha-dihydroprogesterone
  • 5alpha-Pregnane-3,20-dione
  • 5alpha-dihydroprogesterone
LM ID
LMST02030170
Formula
C21H32O2
Exact Mass
Calculate m/z
316.24023
Sum Composition
ST 21:2;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View BMRB ID(NMR) spectrum
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroids [ST02]
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]

Biological Context

5α-Dihydroprogesterone (5α-DHP) is a progesterone receptor agonist and metabolite of progesterone .1 It is formed from progesterone by 5α-reductase.2 It induces gene expression mediated by the progesterone receptor (PR) in reporter assays using HepG2 cells expressing equine PR or human PR (EC50s = 14 and 23.1 nM, respectively).1 5α-DHP (0.7 mg/kg) maintains equine pregnancy in the absence of luteal progesterone. It increases proliferation of C4HD murine mammary cells when used at a concentration of 1 µM and induces tumor formation in a C4HD mouse model of tumorigenesis in a dose-dependent manner.3 5α-DHP levels increase locally following spinal cord injury or traumatic brain injury in rats and ischemic brain injury in mice.2

This information has been provided by Cayman Chemical

References

1. Wiebe, J.P., Rivas, M.A., Mercogliano, M.F., et al. Progesterone-induced stimulation of mammary tumorigenesis is due to the progesterone metabolite, 5α-dihydroprogesterone (5αP) and can be suppressed by the 5α-reductase inhibitor, finasteride. J. Steroid Biochem. Mol. Biol. 149, 27-34 (2015).
2. Guennoun, R., Labombarda, F., Gonzalez Deniselle, M.C., et al. Progesterone and allopregnanolone in the central nervous system: Response to injury and implication for neuroprotection. J. Steroid Biochem. Mol. Biol. 146, 48-61 (2015).
3. Scholtz, E.L., Krishnan, S., Ball, B.A., et al. Pregnancy without progesterone in horses defines a second endogenous biopotent progesterone receptor agonist, 5α-dihydroprogesterone. Proc. Natl. Acad. Sci. USA 111(9), 3365-3370 (2014).

Reactions

Filter by species:
ⓘ Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
Click on an edge to display the reaction(s).
Reactions graph legend

String Representations

InChiKey (Click to copy)
XMRPGKVKISIQBV-BJMCWZGWSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1C[C@]2(C)[C@@H](C(=O)C)CC[C@@]2([H])[C@]2([H])CC[C@@]3([H])CC(CC[C@]3(C)[C@]21[H])=O

Other Databases

KEGG ID
C03681
HMDB ID
HMDB0003759
CHEBI ID
28952
PubChem CID
92810
SwissLipids ID
SLM:000485382
Cayman ID
31505

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 4
Aromatic Rings 0
Rotatable Bonds 1
Van der Waals Molecular Volume 334.72
Topological Polar Surface Area 34.14
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 2
logP 4.80
Molar Refractivity 90.91

Admin

Created at
-
Updated at
-