Structure Database (LMSD)

Common Name
5beta-pregnane-3,20-dione
Systematic Name
5β-pregnane-3,20-dione
Synonyms
  • (5BETA)-PREGNANE-3,20-DIONE
  • 3,20-pregnanedione
  • 5beta-Pregnane-3,20-dione
  • 5beta-dihydroprogesterone
  • 5beta-pregnan-3,20-dione
LM ID
LMST02030146
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 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

5β-Dihydroprogesterone (5β-DHP) is a progesterone receptor agonist and metabolite of progesterone .1,2 It is formed from progesterone by 5β-reductase.2 5β-DHP inhibits spontaneous contractions in isolated rat uterus when used at a concentration of 10 µg/ml, an effect that can be blocked by the progesterone receptor antagonist RU486 (mifepristone) but not the GABAA receptor antagonist picrotoxin .1 It is a negative modulator of homooligomeric ρ1 subunit-containing GABAA receptors, inhibiting GABA-induced currents in X. laevis oocytes expressing these receptors (IC50 = 5.02 µM).3 Plasma levels of 5β-DHP decrease at the onset of spontaneous human labor.4

This information has been provided by Cayman Chemical

References

1. Sheehan, P.M., Rice, G.E., Moses, E.K., et al. 5β-dihydroprogesterone and steroid 5β-reductase decrease in association with human parturition at term. Mol. Hum. Reprod. 11(7), 495-501 (2005).
2. Morris, K.D., Moorefield, C.N., and Amin, J. Differential modulation of the γ-aminobutyric acid type C receptor by neuroactive steroids. Mol. Pharmacol. 56(4), 752-759 (1999).
3. Bumke-Vogt, C., Bähr, V., Diederich, S., et al. Expression of the progesterone receptor and progesterone- metabolising enzymes in the female and male human kidney. J. Endocrinol. 175(2), 349-364 (2002).
4. Putnam, C.D., Brann, D.W., Kolbeck, R.C., et al. Inhibition of uterine contractility by progesterone and progesterone metabolites: Mediation by progesterone and gamma amino butyric acidA receptor systems. Biol. Reprod. 45(2), 266-272 (1991).

Reactions

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String Representations

InChiKey (Click to copy)
XMRPGKVKISIQBV-XWOJZHJZSA-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-/m1/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

Wikipedia
5β-Dihydroprogesterone
KEGG ID
C05479
CHEBI ID
30154
PubChem CID
92745
SwissLipids ID
SLM:000390130
Cayman ID
34644
PDB ID
CI2
GuidePharm ID
2759

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

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Created at
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Updated at
9th Jun 2022